FALSE00016914212025FYhttp://fasb.org/us-gaap/2025#OtherAssetshttp://fasb.org/us-gaap/2025#OtherAssetshttp://fasb.org/us-gaap/2025#AccruedLiabilitiesAndOtherLiabilitieshttp://fasb.org/us-gaap/2025#AccruedLiabilitiesAndOtherLiabilities1169iso4217:USDxbrli:sharesiso4217:USDxbrli:shareslmnd:securityxbrli:purelmnd:segmentlmnd:claimlmnd:directorlmnd:floor00016914212025-01-012025-12-3100016914212025-06-3000016914212026-02-2400016914212025-10-012025-12-3100016914212025-12-3100016914212024-12-3100016914212024-01-012024-12-3100016914212023-01-012023-12-310001691421us-gaap:CommonStockMember2022-12-310001691421us-gaap:AdditionalPaidInCapitalMember2022-12-310001691421us-gaap:RetainedEarningsMember2022-12-310001691421us-gaap:AccumulatedOtherComprehensiveIncomeMember2022-12-3100016914212022-12-310001691421us-gaap:CommonStockMember2023-01-012023-12-310001691421us-gaap:AdditionalPaidInCapitalMember2023-01-012023-12-310001691421us-gaap:RetainedEarningsMember2023-01-012023-12-310001691421us-gaap:AccumulatedOtherComprehensiveIncomeMember2023-01-012023-12-310001691421us-gaap:CommonStockMember2023-12-310001691421us-gaap:AdditionalPaidInCapitalMember2023-12-310001691421us-gaap:RetainedEarningsMember2023-12-310001691421us-gaap:AccumulatedOtherComprehensiveIncomeMember2023-12-3100016914212023-12-310001691421us-gaap:CommonStockMember2024-01-012024-12-310001691421us-gaap:AdditionalPaidInCapitalMember2024-01-012024-12-310001691421us-gaap:CommonStockMember2025-01-012025-12-310001691421us-gaap:RetainedEarningsMember2024-01-012024-12-310001691421us-gaap:AccumulatedOtherComprehensiveIncomeMember2024-01-012024-12-310001691421us-gaap:CommonStockMember2024-12-310001691421us-gaap:AdditionalPaidInCapitalMember2024-12-310001691421us-gaap:RetainedEarningsMember2024-12-310001691421us-gaap:AccumulatedOtherComprehensiveIncomeMember2024-12-310001691421us-gaap:AdditionalPaidInCapitalMember2025-01-012025-12-310001691421us-gaap:RetainedEarningsMember2025-01-012025-12-310001691421us-gaap:AccumulatedOtherComprehensiveIncomeMember2025-01-012025-12-310001691421us-gaap:CommonStockMember2025-12-310001691421us-gaap:AdditionalPaidInCapitalMember2025-12-310001691421us-gaap:RetainedEarningsMember2025-12-310001691421us-gaap:AccumulatedOtherComprehensiveIncomeMember2025-12-310001691421us-gaap:ComputerEquipmentMember2025-12-310001691421lmnd:FurnitureAndEquipmentMember2025-12-310001691421us-gaap:SoftwareDevelopmentMember2025-12-310001691421us-gaap:EmployeeStockOptionMember2025-01-012025-12-310001691421us-gaap:CorporateDebtSecuritiesMember2025-12-310001691421us-gaap:USGovernmentAgenciesDebtSecuritiesMember2025-12-310001691421us-gaap:AssetBackedSecuritiesMember2025-12-310001691421us-gaap:ForeignGovernmentDebtSecuritiesMember2025-12-310001691421us-gaap:CorporateDebtSecuritiesMember2024-12-310001691421us-gaap:USGovernmentAgenciesDebtSecuritiesMember2024-12-310001691421us-gaap:AssetBackedSecuritiesMember2024-12-310001691421us-gaap:ForeignGovernmentDebtSecuritiesMember2024-12-310001691421us-gaap:FixedIncomeSecuritiesMember2025-12-310001691421us-gaap:FixedIncomeSecuritiesMember2024-12-310001691421us-gaap:CashAndCashEquivalentsMember2025-01-012025-12-310001691421us-gaap:CashAndCashEquivalentsMember2024-01-012024-12-310001691421us-gaap:CashAndCashEquivalentsMember2023-01-012023-12-310001691421us-gaap:DebtSecuritiesMember2025-01-012025-12-310001691421us-gaap:DebtSecuritiesMember2024-01-012024-12-310001691421us-gaap:DebtSecuritiesMember2023-01-012023-12-310001691421us-gaap:ShortTermInvestmentsMember2025-01-012025-12-310001691421us-gaap:ShortTermInvestmentsMember2024-01-012024-12-310001691421us-gaap:ShortTermInvestmentsMember2023-01-012023-12-310001691421lmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421lmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:DElmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:DElmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:NYlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:NYlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:WAlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:WAlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:COlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:COlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:VAlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:VAlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:NMlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:NMlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:OHlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:OHlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:NJlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:NJlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:NClmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:NClmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:NVlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:NVlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:ARlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:ARlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:FLlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:FLlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:MAlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:MAlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:KSlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:KSlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:KYlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:KYlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421stpr:GAlmnd:DepositWithStateInsuranceDepartmentMember2025-12-310001691421stpr:GAlmnd:DepositWithStateInsuranceDepartmentMember2024-12-310001691421us-gaap:CorporateDebtSecuritiesMemberus-gaap:FairValueInputsLevel1Member2025-12-310001691421us-gaap:CorporateDebtSecuritiesMemberus-gaap:FairValueInputsLevel2Member2025-12-310001691421us-gaap:CorporateDebtSecuritiesMemberus-gaap:FairValueInputsLevel3Member2025-12-310001691421us-gaap:USGovernmentAgenciesDebtSecuritiesMemberus-gaap:FairValueInputsLevel1Member2025-12-310001691421us-gaap:USGovernmentAgenciesDebtSecuritiesMemberus-gaap:FairValueInputsLevel2Member2025-12-310001691421us-gaap:USGovernmentAgenciesDebtSecuritiesMemberus-gaap:FairValueInputsLevel3Member2025-12-310001691421us-gaap:AssetBackedSecuritiesMemberus-gaap:FairValueInputsLevel1Member2025-12-310001691421us-gaap:AssetBackedSecuritiesMemberus-gaap:FairValueInputsLevel2Member2025-12-310001691421us-gaap:AssetBackedSecuritiesMemberus-gaap:FairValueInputsLevel3Member2025-12-310001691421us-gaap:ForeignGovernmentDebtSecuritiesMemberus-gaap:FairValueInputsLevel1Member2025-12-310001691421us-gaap:ForeignGovernmentDebtSecuritiesMemberus-gaap:FairValueInputsLevel2Member2025-12-310001691421us-gaap:ForeignGovernmentDebtSecuritiesMemberus-gaap:FairValueInputsLevel3Member2025-12-310001691421us-gaap:FairValueInputsLevel1Member2025-12-310001691421us-gaap:FairValueInputsLevel2Member2025-12-310001691421us-gaap:FairValueInputsLevel3Member2025-12-310001691421us-gaap:WarrantMemberus-gaap:FairValueInputsLevel1Member2025-12-310001691421us-gaap:WarrantMemberus-gaap:FairValueInputsLevel2Member2025-12-310001691421us-gaap:WarrantMemberus-gaap:FairValueInputsLevel3Member2025-12-310001691421us-gaap:WarrantMember2025-12-310001691421us-gaap:CorporateDebtSecuritiesMemberus-gaap:FairValueInputsLevel1Member2024-12-310001691421us-gaap:CorporateDebtSecuritiesMemberus-gaap:FairValueInputsLevel2Member2024-12-310001691421us-gaap:CorporateDebtSecuritiesMemberus-gaap:FairValueInputsLevel3Member2024-12-310001691421us-gaap:USGovernmentAgenciesDebtSecuritiesMemberus-gaap:FairValueInputsLevel1Member2024-12-310001691421us-gaap:USGovernmentAgenciesDebtSecuritiesMemberus-gaap:FairValueInputsLevel2Member2024-12-310001691421us-gaap:USGovernmentAgenciesDebtSecuritiesMemberus-gaap:FairValueInputsLevel3Member2024-12-310001691421us-gaap:AssetBackedSecuritiesMemberus-gaap:FairValueInputsLevel1Member2024-12-310001691421us-gaap:AssetBackedSecuritiesMemberus-gaap:FairValueInputsLevel2Member2024-12-310001691421us-gaap:AssetBackedSecuritiesMemberus-gaap:FairValueInputsLevel3Member2024-12-310001691421us-gaap:ForeignGovernmentDebtSecuritiesMemberus-gaap:FairValueInputsLevel1Member2024-12-310001691421us-gaap:ForeignGovernmentDebtSecuritiesMemberus-gaap:FairValueInputsLevel2Member2024-12-310001691421us-gaap:ForeignGovernmentDebtSecuritiesMemberus-gaap:FairValueInputsLevel3Member2024-12-310001691421us-gaap:FairValueInputsLevel1Member2024-12-310001691421us-gaap:FairValueInputsLevel2Member2024-12-310001691421us-gaap:FairValueInputsLevel3Member2024-12-310001691421us-gaap:WarrantMemberus-gaap:FairValueInputsLevel1Member2024-12-310001691421us-gaap:WarrantMemberus-gaap:FairValueInputsLevel2Member2024-12-310001691421us-gaap:WarrantMemberus-gaap:FairValueInputsLevel3Member2024-12-310001691421us-gaap:WarrantMember2024-12-310001691421Reinsurance Program2024-07-012024-07-0100016914212023-07-012023-07-010001691421Proportional Reinsurance Contracts2023-07-012023-07-010001691421srt:MaximumMemberProperty Per Risk Excess of Loss Reinsurance2023-07-012023-07-010001691421Property Per Risk Excess of Loss Reinsurance2023-07-012023-07-010001691421lmnd:LemonadeInsuranceCompanyMemberAutomatic Facultative Property Per Risk Excess of Loss2024-06-302024-06-300001691421lmnd:LemonadeInsuranceCompanyMemberAutomatic Facultative Property Per Risk Excess of Loss Reinsurance2024-06-302024-06-300001691421Excess of Loss Reinsurance Contract2023-07-012023-07-010001691421lmnd:HannoverRueckSEMembersrt:AMBestAPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421lmnd:HannoverRueckSEMembersrt:AMBestAPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421lmnd:MAPFREReCompaniaDeReasegurosSAMembersrt:AMBestARatingMemberus-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421lmnd:MAPFREReCompaniaDeReasegurosSAMembersrt:AMBestARatingMemberus-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421lmnd:SwissReinsuranceAmericaCorporationMembersrt:AMBestAPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421lmnd:SwissReinsuranceAmericaCorporationMembersrt:AMBestAPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421lmnd:AvivaInsuranceLimitedMembersrt:AMBestAPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421lmnd:AvivaInsuranceLimitedMembersrt:AMBestAPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421lmnd:LloydsUnderwriterSyndicateNo2791MAPMemberus-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421lmnd:LloydsUnderwriterSyndicateNo2791MAPMemberus-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421lmnd:TokioMarineNichidoFireInsuranceCompanyLimitedMembersrt:AMBestAPlusPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421lmnd:TokioMarineNichidoFireInsuranceCompanyLimitedMembersrt:AMBestAPlusPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421lmnd:LloydsUnderwriterSyndicateNo1084CSLMemberus-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421lmnd:LloydsUnderwriterSyndicateNo1084CSLMemberus-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421lmnd:TheTravellersIndemnityCompanyMembersrt:AMBestAPlusPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421lmnd:TheTravellersIndemnityCompanyMembersrt:AMBestAPlusPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421lmnd:OdysseyReinsuranceCompanyMembersrt:AMBestAPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421lmnd:OdysseyReinsuranceCompanyMembersrt:AMBestAPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421lmnd:LloydsUnderwriterSyndicateNo2001AMLMembersrt:AMBestAPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421lmnd:LloydsUnderwriterSyndicateNo2001AMLMembersrt:AMBestAPlusRatingMemberus-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421lmnd:TopReinsurersMemberus-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421lmnd:TopReinsurersMemberus-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421lmnd:OtherReinsurersMemberus-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421lmnd:OtherReinsurersMemberus-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421us-gaap:CededCreditRiskUnsecuredMember2025-12-310001691421us-gaap:CededCreditRiskUnsecuredMember2024-12-310001691421lmnd:ComputerEquipmentAndSoftwareMember2025-12-310001691421lmnd:ComputerEquipmentAndSoftwareMember2024-12-310001691421us-gaap:LeaseholdImprovementsMember2025-12-310001691421us-gaap:LeaseholdImprovementsMember2024-12-310001691421lmnd:FurnitureAndEquipmentMember2024-12-310001691421lmnd:InsuranceLicensesMember2025-12-310001691421lmnd:InsuranceLicensesMember2024-12-310001691421us-gaap:TrademarksMember2025-12-310001691421us-gaap:TrademarksMember2024-12-310001691421lmnd:TechnologyMember2025-01-012025-12-310001691421lmnd:TechnologyMember2025-12-310001691421lmnd:TechnologyMember2024-12-310001691421lmnd:ValueOfBusinessAcquiredMember2025-01-012025-12-310001691421lmnd:ValueOfBusinessAcquiredMember2025-12-310001691421lmnd:ValueOfBusinessAcquiredMember2024-12-310001691421lmnd:CaliforniaWildfiresMember2025-01-012025-12-310001691421lmnd:CaliforniaWildfiresMember2025-03-012025-03-310001691421lmnd:HurricaneHeleneMember2024-01-012024-12-310001691421lmnd:HurricaneBerylMember2024-01-012024-12-310001691421lmnd:WinterStormElliotMember2023-01-012023-12-310001691421lmnd:TexasHailStormMember2023-01-012023-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2016-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2017-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2018-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2019-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2020-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2021-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2022-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2023-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2024-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2025-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2017-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2018-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2019-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2020-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2021-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2022-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2023-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2024-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2025-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2018-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2019-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2020-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2021-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2022-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2023-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2024-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2025-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2019-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2020-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2021-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2022-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2023-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2024-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2025-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2020-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2021-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2022-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2023-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2024-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2025-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2021-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2022-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2023-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2024-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2025-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2022Member2022-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2022Member2023-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2022Member2024-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2022Member2025-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2023Member2023-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2023Member2024-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2023Member2025-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2024Member2024-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2024Member2025-12-310001691421us-gaap:PropertyInsuranceProductLineMemberus-gaap:ShortDurationInsuranceContractAccidentYear2025Member2025-12-310001691421us-gaap:PropertyInsuranceProductLineMember2025-12-310001691421us-gaap:PropertyInsuranceProductLineMember2023-12-310001691421us-gaap:PropertyInsuranceProductLineMember2022-12-310001691421us-gaap:PropertyInsuranceProductLineMember2020-12-310001691421us-gaap:PropertyInsuranceProductLineMember2024-12-310001691421us-gaap:PropertyInsuranceProductLineMember2016-12-310001691421us-gaap:PropertyInsuranceProductLineMember2017-12-310001691421us-gaap:PropertyInsuranceProductLineMember2019-12-310001691421us-gaap:PropertyInsuranceProductLineMember2021-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2020-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2021-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2022-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2023-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2024-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2025-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2021-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2022-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2023-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2024-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2025-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2022Member2022-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2022Member2023-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2022Member2024-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2022Member2025-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2023Member2023-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2023Member2024-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2023Member2025-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2024Member2024-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2024Member2025-12-310001691421lmnd:PetInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2025Member2025-12-310001691421lmnd:PetInsuranceMember2025-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2016-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2017-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2018-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2019-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2020-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2021-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2022-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2023-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2024-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortdurationInsuranceContractsAccidentYear2016Member2025-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2017-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2018-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2019-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2020-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2021-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2022-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2023-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2024-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2017Member2025-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2018-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2019-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2020-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2021-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2022-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2023-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2024-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractsAccidentYear2018Member2025-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2019-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2020-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2021-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2022-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2023-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2024-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2019Member2025-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2020-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2021-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2022-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2023-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2024-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2020Member2025-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2021-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2022-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2023-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2024-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2021Member2025-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2022Member2022-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2022Member2023-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2022Member2024-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2022Member2025-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2023Member2023-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2023Member2024-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2023Member2025-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2024Member2024-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2024Member2025-12-310001691421lmnd:CarInsuranceMemberus-gaap:ShortDurationInsuranceContractAccidentYear2025Member2025-12-310001691421lmnd:CarInsuranceMember2025-12-310001691421lmnd:CustomerInvestmentAgreementMemberus-gaap:LineOfCreditMember2023-06-280001691421lmnd:CustomerInvestmentAgreementMemberus-gaap:LineOfCreditMember2023-06-282023-06-280001691421lmnd:AmendedAndRestatedCustomerInvestmentAgreementMemberus-gaap:LineOfCreditMember2024-01-080001691421lmnd:AmendedAndRestatedCustomerInvestmentAgreementMemberus-gaap:LineOfCreditMember2025-02-030001691421lmnd:GCCustomerValueArrangerLLCMemberlmnd:CustomerInvestmentAgreementMemberus-gaap:LineOfCreditMember2023-06-282023-06-280001691421lmnd:CustomerInvestmentAgreementMemberus-gaap:LineOfCreditMember2025-12-310001691421lmnd:CustomerInvestmentAgreementMemberus-gaap:LineOfCreditMember2024-12-310001691421lmnd:CustomerInvestmentAgreementMemberus-gaap:LineOfCreditMember2025-01-012025-12-310001691421lmnd:CustomerInvestmentAgreementMemberus-gaap:LineOfCreditMember2024-01-012024-12-310001691421lmnd:CustomerInvestmentAgreementMemberus-gaap:LineOfCreditMember2023-01-012023-12-310001691421lmnd:LemonadeFoundationMembersrt:AffiliatedEntityMember2020-01-012020-12-310001691421lmnd:LemonadeInc.Membersrt:AffiliatedEntityMemberlmnd:LemonadeFoundationMember2024-12-310001691421lmnd:LemonadeInc.Membersrt:AffiliatedEntityMemberlmnd:LemonadeFoundationMember2025-12-310001691421lmnd:OmnibusAgreementMemberus-gaap:WarrantMember2022-12-310001691421lmnd:OmnibusAgreementMember2022-12-310001691421lmnd:OmnibusAgreementMember2022-01-012022-12-310001691421lmnd:OmnibusAgreementMemberus-gaap:WarrantMember2025-04-040001691421lmnd:IncentiveCompensationPlan2020Member2020-07-020001691421lmnd:IncentiveCompensationPlan2020Member2020-07-022020-07-020001691421lmnd:IncentiveCompensationPlan2020Member2025-12-310001691421lmnd:EmployeeStockPurchasePlan2020Member2020-07-020001691421lmnd:EmployeeStockPurchasePlan2020Member2020-07-022020-07-020001691421lmnd:EmployeeStockPurchasePlan2020Member2025-12-310001691421lmnd:IncentiveShareOptionPlan2015Memberus-gaap:EmployeeStockOptionMember2015-07-012015-07-310001691421lmnd:IncentiveShareOptionPlan2015Member2015-07-310001691421lmnd:IncentiveShareOptionPlan2015Member2025-12-310001691421lmnd:IncentiveStockPlan2021Member2022-01-012022-12-310001691421lmnd:IncentiveCompensationPlan2020Memberus-gaap:SubsequentEventMember2026-01-012026-01-010001691421lmnd:EmployeeSharePurchasePlanESPPMember2026-01-012026-01-010001691421us-gaap:EmployeeStockOptionMember2024-01-012024-12-310001691421us-gaap:RestrictedStockUnitsRSUMember2024-12-310001691421us-gaap:RestrictedStockUnitsRSUMember2025-01-012025-12-310001691421us-gaap:RestrictedStockUnitsRSUMember2025-12-310001691421lmnd:ClaimsAndClaimsAdjustmentExpenseMember2025-01-012025-12-310001691421lmnd:ClaimsAndClaimsAdjustmentExpenseMember2024-01-012024-12-310001691421lmnd:ClaimsAndClaimsAdjustmentExpenseMember2023-01-012023-12-310001691421lmnd:OtherInsuranceExpenseMember2025-01-012025-12-310001691421lmnd:OtherInsuranceExpenseMember2024-01-012024-12-310001691421lmnd:OtherInsuranceExpenseMember2023-01-012023-12-310001691421us-gaap:SellingAndMarketingExpenseMember2025-01-012025-12-310001691421us-gaap:SellingAndMarketingExpenseMember2024-01-012024-12-310001691421us-gaap:SellingAndMarketingExpenseMember2023-01-012023-12-310001691421us-gaap:ResearchAndDevelopmentExpenseMember2025-01-012025-12-310001691421us-gaap:ResearchAndDevelopmentExpenseMember2024-01-012024-12-310001691421us-gaap:ResearchAndDevelopmentExpenseMember2023-01-012023-12-310001691421us-gaap:GeneralAndAdministrativeExpenseMember2025-01-012025-12-310001691421us-gaap:GeneralAndAdministrativeExpenseMember2024-01-012024-12-310001691421us-gaap:GeneralAndAdministrativeExpenseMember2023-01-012023-12-310001691421us-gaap:WarrantMember2025-01-012025-12-310001691421us-gaap:WarrantMember2024-01-012024-12-310001691421us-gaap:WarrantMember2023-01-012023-12-310001691421us-gaap:EmployeeStockOptionMember2023-01-012023-12-310001691421us-gaap:RestrictedStockUnitsRSUMember2024-01-012024-12-310001691421us-gaap:RestrictedStockUnitsRSUMember2023-01-012023-12-310001691421us-gaap:EmployeeStockOptionMember2025-12-310001691421lmnd:OmnibusAgreementMemberus-gaap:WarrantMember2022-01-012022-12-310001691421lmnd:OmnibusAgreementMemberus-gaap:WarrantMember2024-04-300001691421country:IL2025-01-012025-12-310001691421country:IL2024-01-012024-12-310001691421country:IL2023-01-012023-12-310001691421us-gaap:ForeignTaxJurisdictionOtherMember2025-01-012025-12-310001691421us-gaap:ForeignTaxJurisdictionOtherMember2024-01-012024-12-310001691421country:US2025-01-012025-12-310001691421country:US2024-01-012024-12-310001691421country:US2023-01-012023-12-310001691421country:NL2025-01-012025-12-310001691421country:NL2024-01-012024-12-310001691421country:NL2023-01-012023-12-310001691421us-gaap:DomesticCountryMember2025-12-310001691421us-gaap:StateAndLocalJurisdictionMember2025-12-310001691421us-gaap:EmployeeStockOptionMember2025-01-012025-12-310001691421us-gaap:EmployeeStockOptionMember2024-01-012024-12-310001691421us-gaap:EmployeeStockOptionMember2023-01-012023-12-310001691421us-gaap:RestrictedStockMember2025-01-012025-12-310001691421us-gaap:RestrictedStockMember2024-01-012024-12-310001691421us-gaap:RestrictedStockMember2023-01-012023-12-310001691421us-gaap:WarrantMember2025-01-012025-12-310001691421us-gaap:WarrantMember2024-01-012024-12-310001691421us-gaap:WarrantMember2023-01-012023-12-310001691421lmnd:MetromileMember2024-01-012024-12-310001691421lmnd:MetromileMember2025-01-012025-12-310001691421lmnd:MetromileMember2023-01-012023-12-310001691421us-gaap:RelatedPartyMember2025-12-310001691421lmnd:LemonadeFoundationMembersrt:AffiliatedEntityMember2025-01-012025-12-310001691421lmnd:LemonadeFoundationMembersrt:AffiliatedEntityMember2025-12-310001691421lmnd:LemonadeFoundationMembersrt:AffiliatedEntityMember2024-12-310001691421us-gaap:PropertyLeaseGuaranteeMember2025-12-310001691421lmnd:CaliforniaWildfiresMember2025-02-280001691421stpr:NY2025-01-012025-12-310001691421lmnd:AmsterdamMember2025-01-012025-12-310001691421lmnd:TelAvivMember2025-01-012025-12-310001691421lmnd:SanFranciscoMember2025-01-012025-12-310001691421stpr:NY2023-09-300001691421stpr:NY2024-01-012024-12-310001691421stpr:NY2023-01-012023-12-310001691421lmnd:SanFranciscoMember2024-01-012024-12-310001691421lmnd:SanFranciscoMember2023-01-012023-12-310001691421lmnd:LemonadeInsuranceCompanyMember2025-12-310001691421lmnd:LemonadeInsuranceCompanyMember2024-12-310001691421lmnd:MetromileInsuranceCompanyMember2025-12-310001691421lmnd:MetromileInsuranceCompanyMember2024-12-310001691421lmnd:ReportableSegmentMember2025-01-012025-12-310001691421lmnd:ReportableSegmentMember2024-01-012024-12-310001691421lmnd:ReportableSegmentMember2023-01-012023-12-310001691421us-gaap:DomesticCountryMemberlmnd:CARESActERCProgramMember2025-01-012025-12-310001691421stpr:NY2024-01-012024-12-310001691421lmnd:MetromileMember2023-12-310001691421stpr:CA2025-01-012025-12-310001691421stpr:CAus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421stpr:CA2024-01-012024-12-310001691421stpr:CAus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421stpr:CA2023-01-012023-12-310001691421stpr:CAus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421stpr:TX2025-01-012025-12-310001691421stpr:TXus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421stpr:TX2024-01-012024-12-310001691421stpr:TXus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421stpr:TX2023-01-012023-12-310001691421stpr:TXus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421stpr:NY2025-01-012025-12-310001691421stpr:NYus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421stpr:NYus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421stpr:NY2023-01-012023-12-310001691421stpr:NYus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421stpr:WA2025-01-012025-12-310001691421stpr:WAus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421stpr:WA2024-01-012024-12-310001691421stpr:WAus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421stpr:WA2023-01-012023-12-310001691421stpr:WAus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421stpr:IL2025-01-012025-12-310001691421stpr:ILus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421stpr:IL2024-01-012024-12-310001691421stpr:ILus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421stpr:IL2023-01-012023-12-310001691421stpr:ILus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421stpr:NJ2025-01-012025-12-310001691421stpr:NJus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421stpr:NJ2024-01-012024-12-310001691421stpr:NJus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421stpr:NJ2023-01-012023-12-310001691421stpr:NJus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421stpr:CO2025-01-012025-12-310001691421stpr:COus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421stpr:CO2024-01-012024-12-310001691421stpr:COus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421stpr:CO2023-01-012023-12-310001691421stpr:COus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421stpr:FL2025-01-012025-12-310001691421stpr:FLus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421stpr:FL2024-01-012024-12-310001691421stpr:FLus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421stpr:FL2023-01-012023-12-310001691421stpr:FLus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421stpr:PA2025-01-012025-12-310001691421stpr:PAus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421stpr:PA2024-01-012024-12-310001691421stpr:PAus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421stpr:PA2023-01-012023-12-310001691421stpr:PAus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421stpr:AZ2025-01-012025-12-310001691421stpr:AZus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421stpr:AZ2024-01-012024-12-310001691421stpr:AZus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421stpr:AZ2023-01-012023-12-310001691421stpr:AZus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421lmnd:AllOtherStatesMember2025-01-012025-12-310001691421lmnd:AllOtherStatesMemberus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421lmnd:AllOtherStatesMember2024-01-012024-12-310001691421lmnd:AllOtherStatesMemberus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421lmnd:AllOtherStatesMember2023-01-012023-12-310001691421lmnd:AllOtherStatesMemberus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421country:US2025-01-012025-12-310001691421country:USus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421country:US2024-01-012024-12-310001691421country:USus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421country:US2023-01-012023-12-310001691421country:USus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421lmnd:EuropeAndUintedKindomMember2025-01-012025-12-310001691421lmnd:EuropeAndUintedKindomMemberus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421lmnd:EuropeAndUintedKindomMember2024-01-012024-12-310001691421lmnd:EuropeAndUintedKindomMemberus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421lmnd:EuropeAndUintedKindomMember2023-01-012023-12-310001691421lmnd:EuropeAndUintedKindomMemberus-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421us-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2025-01-012025-12-310001691421us-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2024-01-012024-12-310001691421us-gaap:GeographicConcentrationRiskMemberlmnd:PremiumsWrittenGrossBenchmarkMember2023-01-012023-12-310001691421us-gaap:ValuationAllowanceOfDeferredTaxAssetsMember2024-12-310001691421us-gaap:ValuationAllowanceOfDeferredTaxAssetsMember2025-01-012025-12-310001691421us-gaap:ValuationAllowanceOfDeferredTaxAssetsMember2025-12-310001691421us-gaap:AllowanceForUncollectiblePremiumsReceivableMember2024-12-310001691421us-gaap:AllowanceForUncollectiblePremiumsReceivableMember2025-01-012025-12-310001691421us-gaap:AllowanceForUncollectiblePremiumsReceivableMember2025-12-310001691421us-gaap:ValuationAllowanceOfDeferredTaxAssetsMember2023-12-310001691421us-gaap:ValuationAllowanceOfDeferredTaxAssetsMember2024-01-012024-12-310001691421us-gaap:AllowanceForUncollectiblePremiumsReceivableMember2023-12-310001691421us-gaap:AllowanceForUncollectiblePremiumsReceivableMember2024-01-012024-12-310001691421lmnd:OfficerTradingArrangementMember2025-01-012025-12-310001691421lmnd:MayaProsorMember2025-10-012025-12-310001691421lmnd:MayaProsorMember2025-12-31

(Exact name of Registrant as specified in its charter)

(Address of principal executive offices) (Zip Code)

(Registrant’s telephone number including area code)

Securities registered pursuant to Section 12(b) of the Act:

Securities registered pursuant to Section 12(g) of the Act: None

Indicate by check mark if the registrant is a well-known seasoned issuer, as defined in Rule 405 of the Securities Act.     ☑ Yes ☐ No

Indicate by check mark if the registrant is not required to file reports pursuant to Section 13 or Section 15(d) of the Act.     ☐ Yes ☑ No

Indicate by check mark whether the registrant (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days.                                ☑ Yes ☐ No

Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§ 232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit such files). ☑ Yes ☐ No

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company. See the definitions of "large accelerated filer," "accelerated filer," "smaller reporting company," and "emerging growth company" in Rule 12b-2 of the Exchange Act.

Large accelerated filer

☑

Accelerated filer

☐

Non-accelerated filer

☐

Smaller reporting company

☐

Emerging growth company

☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

Indicate by check mark whether the registrant has filed a report on and attestation to its management’s assessment of the effectiveness of its internal control over financial reporting under Section 404(b) of the Sarbanes-Oxley Act (15 U.S.C. 7262(b)) by the registered public accounting firm that prepared or issued its audit report. ☑

If securities are registered pursuant to Section 12(b) of the Act, indicate by check mark whether the financial statements of the registrant included in the filing reflect the correction of an error to previously issued financial statements. ☐

Indicate by check mark whether any of those error corrections are restatements that required a recovery analysis of incentive-based compensation received by any of the registrant’s executive officers during the relevant recovery period pursuant to §240.10D-1(b). ☐

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Act).        ☐ Yes ☑ No

The aggregate market value of the common stock held by non-affiliates of the registrant, based on the closing sales price of $43.81 on June 30, 2025, was approximately $2,880,712,049.

Registrant had 76,383,438 shares of common stock outstanding as of February 24, 2026.

Portions of the Registrant’s definitive Proxy Statement relating to its 2026 Annual Meeting of Stockholders, to be filed with the Securities and Exchange Commission within 120 days after the end of the fiscal year to which this report relates, are incorporated by reference into Part III of this Annual Report on Form 10-K where indicated.

This Annual Report on Form 10-K (the “Annual Report”) contains forward-looking statements. We intend such forward-looking statements to be covered by the safe harbor provisions for forward-looking statements contained in Section 27A of the Securities Act of 1933, as amended and Section 21E of the Securities Exchange Act of 1934, as amended, or the Exchange Act. All statements other than statements of historical fact contained in this Annual Report are forward-looking statements, including without limitation, statements regarding our future results of operations and financial position, our ability to expand our business, our ability to effectively manage the growth of our business, our ability to achieve profitability, our ability to attract, retain and expand our customer base, our ability to operate under and maintain our business model, our ability to maintain and enhance our brand and reputation, the effects of seasonal trends on our results of operations, the impact of catastrophe events or natural disasters on our results of operations, our ability to attain greater value from each customer, our ability to compete effectively in our industry, the future performance of the markets in which we operate, our ability to maintain reinsurance contracts, the adequacy of our loss and loss adjustment reserves, the impact of the evolving conflict in Israel and surrounding region, the potential effects of macroeconomic conditions including inflation, changes in trade policy and tariffs on our claims costs and results of operations, our ability to develop and deploy artificial intelligence and technology, our ability to expand into new products and geographic markets, anticipated benefits of and our ability to maintain our financing arrangements, the impact of current and future laws and regulations including tax legislation, the sufficiency of our capital and liquidity, and the plans and objectives of management for future operations and capital expenditures. These statements involve known and unknown risks, uncertainties and other important factors that may cause our actual results, performance or achievements to be materially different from any future results, performance or achievements expressed or implied by the forward-looking statements.

In some cases, you can identify forward-looking statements by terms such as “may,” “will,” “should,” “expect,” “plan,” “anticipate,” “could,” “intend,” “target,” “project,” “contemplate,” “believe,” “estimate,” “predict,” “potential”, or “continue” or the negative of these terms or other similar expressions. The forward-looking statements in this Annual Report are only predictions. We have based these forward-looking statements largely on our current expectations and projections about future events and financial trends that we believe may affect our business, financial condition and results of operations. These forward-looking statements speak only as of the date of this Annual Report and are subject to a number of important factors that could cause actual results to differ materially from those in the forward-looking statements, including the factors described under the sections in this Annual Report titled “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations.”

You should read this Annual Report and the documents that we reference in this Annual Report completely and with the understanding that our actual future results may be materially different from what we expect. We qualify all of our forward-looking statements by these cautionary statements. Except as required by applicable law, we do not plan to publicly update or revise any forward-looking statements contained herein, whether as a result of any new information, future events, changed circumstances or otherwise.

In this Annual Report, unless we indicate otherwise or the context otherwise requires, "Lemonade," the “Company," "we," "our," "ours" and "us" refer to Lemonade, Inc. and its consolidated subsidiaries, including Lemonade Insurance Company, Lemonade Insurance Agency, LLC, Metromile, Inc. and Metromile Insurance Company.

Our business is subject to numerous risks and uncertainties, including those described in Part I Item 1A. “Risk Factors” in this Annual Report. You should carefully consider these risks and uncertainties, together with all of the other information contained in this Annual Report, when investing in our common stock. The principal risks and uncertainties affecting our business include the following:

•We have a history of losses and we may not achieve or maintain profitability in the future.

•Our success and ability to grow our business depend on retaining and expanding our customer base.

•Denial of claims or our failure to accurately and timely pay claims could materially and adversely affect our business, financial condition, results of operations, and prospects.

•Our future revenue growth depends on our ability to increase the lifetime value of our customers and attaining greater value from each customer.

•Intense competition in the segments of the insurance industry in which we operate could negatively affect our ability to attain or increase profitability.

•Our proprietary artificial intelligence algorithms may not operate properly or as we expect them to which could cause us to write policies we should not write, price those policies inappropriately or overpay claims that are made by our customers.

•Failure to maintain our risk-based capital at the required levels could adversely affect the ability of our insurance subsidiaries to maintain regulatory authority to conduct our business.

•If we are unable to maintain and implement relationships with third-party service providers, or renew contracts with them on favorable terms, or if those parties are adversely impacted by financial, reputational, regulatory and other tasks, our prospects for future growth and our business may be adversely affected.

•If we are unable to expand our product offerings, or penetrate new markets, our future growth may be limited.

•We rely on artificial intelligence, telematics, mobile technology, and our digital platforms to collect data and any legal or regulatory requirements that prohibit or restrict our ability to collect or use this data could adversely affect our business.

•If we are unable to underwrite risks accurately and charge competitive yet profitable rates our business will be adversely affected.

•Our pricing model for self-driving technologies and reliance on direct vehicle telemetry may not function as expected.

•We may require additional capital to grow our business, which may not be available on terms acceptable to us or at all.

•Interruptions or delays in the services provided by our sole provider of third-party data centers could impair the operability of our website.

•Security incidents or real or perceived errors, failures or bugs in our systems could impair our operations.

•We are periodically subject to examinations by our primary state insurance regulators, which could result in adverse examination findings and necessitate remedial actions.

•Reinsurance may be unavailable at current levels and prices, which may limit our ability to write new business and impact our capital needs.

•We may face particular privacy, data security, and data protection risks as we continue to expand into Europe and the UK in connection with the GDPR and other data protection regulations.

•We may be unable to prevent or address the misappropriation of our data.

•If our customers were to claim that the policies they purchased failed to provide adequate or appropriate coverage, we could face claims.

•Our product development cycles are complex and subject to regulatory approval, and we may incur significant expenses before we generate revenues.

•Litigation and legal proceedings filed by or against us and our subsidiaries could have a material adverse effect.

•The "Lemonade" brand may not become as widely known as incumbents' brands or the brand may become tarnished.

•Our expansion within the United States and any future international expansion strategy will subject us to additional costs and risks.

•There may be an adverse impact of the Customer Investment Agreement.

•We are subject to extensive insurance industry regulations.

•Severe weather events and other catastrophes are inherently unpredictable and may have a material adverse effect on our financial results and financial condition.

•We rely on data from our customers and third parties for pricing and underwriting our insurance policies handling claims and maximizing automation, the unavailability or inaccuracy of which could limit the functionality of our products and disrupt our business.

•Our results of operations and financial condition may be adversely affected due to limitations in the analytical models used to assess and predict our exposure to catastrophe losses.

•Our actual incurred losses may be greater than our loss and loss adjustment expense reserves, which could have a material adverse effect on our financial condition and results of operations.

•Our insurance subsidiaries are subject to minimum capital and surplus requirements, and our failure to meet these requirements could subject us to regulatory action.

Lemonade is rebuilding insurance from the ground up on a digital substrate and an innovative business model. By leveraging technology, data, artificial intelligence, contemporary design, and social impact, we believe we are making insurance more delightful, more affordable, and more precise. To that end, we have built a vertically-integrated company with wholly-owned insurance carriers in the United States and Europe, including the UK, and the full technology stack to power them.

A brief chat with our bot, AI Maya, is all it takes to get covered with renters, homeowners, pet, car or life insurance, and we expect to offer a similar experience for other insurance products over time. Claims are filed by chatting with another bot, AI Jim, who pays claims in as little as two seconds. This breezy experience belies the extraordinary technology that enables it: a state-of-the-art platform that spans marketing to underwriting, customer care to claims processing, finance to regulation. Our architecture melds artificial intelligence with the human kind, and learns from the prodigious data it generates to become ever better at delighting customers and evaluating risk.

In addition to digitizing insurance end-to-end, we also reimagined the underlying business model to minimize volatility while maximizing trust and social impact. To lessen the volatility inherent in an industry directly impacted by the weather, we utilize several forms of reinsurance, with the goal of reducing the impact on our gross margin.

At the foundation of our business model is a direct, digital, customer-centric experience that enables rapid growth and strong retention. Our customer-centricity runs deep, and our underlying business model is designed to align interests between us and our customers. This technology-first customer acquisition and retention strategy, combined with our unconflicted business model, results in a highly attractive financial model.

We leverage technology in everything we do. AI Maya and our APIs sell 98% of Lemonade's policies. Homeowners insurance policies in the United States are sold primarily via agents, making a platform that finds, onboards, and digitally serves consumers end-to-end very much an outlier. Our digital substrate enables us to integrate marketing and onboarding with underwriting and claims processing, collecting and deploying data throughout, to constantly drive efficient customer acquisition, enhance the customer experience, and mitigate risk. This approach results in significant, rapid scaling coupled with high customer satisfaction.

To align our interests with those of our customers, encourage good behavior and build a long-term relationship based on mutual trust, we endeavor to decouple our financial incentives from variability in claims. Unlike many of our competitors, we work to minimize incentives to deny legitimate claims as we aim to give back, rather than keep the remaining monies. Our reinsurance contracts lessen the volatility in our operating results, as a portion of claims are borne by our reinsurance partners. See "Risk Factors - Risks Relating to Our Business”. In the future, reinsurance may be unavailable at current levels and prices, which may limit our ability to write new business and impact our capital needs. Furthermore, reinsurance subjects us to counterparty risk and may not be adequate to protect us against losses, which could have a material effect on our results of operations and financial condition.

After our customers purchase a policy, we ask them to designate a charitable cause for us to support. As a result, we believe customers are less inclined to embellish claims as they could be hurting a nonprofit they care about, rather than an insurance company they do not.

Strong retention rates and a subscription-based model create highly-recurring and naturally-growing revenue streams, and provide visibility into our topline results. Our reinsurance construct, in turn, mitigates the volatility inherent in traditional insurance companies, where profits quite literally depend on the weather. With our reinsurance agreements reducing the impact of excess claims, and our Giveback policy, we have two powerful ballasts that reduce volatility, while creating an aligned, trustful, and values-rich relationship with our customers.

This combination of a customer-focused onboarding experience, a customer-aligned business model, and a revenue stream that grows along with our customers' insurance needs, has created a sustainable financial model that we are proud of. Over time, we believe our platform will continue to efficiently acquire new customers and give us the ability to service their growing needs at a lower cost, and with higher satisfaction levels, than the industry at large.

Our proprietary and entirely integrated technology stack is a key enabler of our strategy and business model. Interactions with our customers across our platform generate a trove of data, which in turn improves interactions with our customers across our platform.

AI Maya, our playful onboarding and customer experience bot, uses natural language to guide customers through an easy and fun process of joining Lemonade. Maya handles everything from collecting information and personalizing coverage to creating quotes and facilitating payments securely. By asking customers a limited number of high-impact questions, and adapting based on their responses, AI Maya is able to dramatically reduce onboarding times while still collecting and utilizing the data that is central to our continuous improvement.

AI Jim is our claims bot, and, as of December 31, 2025, 96% of the time, it is AI Jim that will take the first notice of loss from a Lemonade customer without human intervention (and with zero claims overhead, known as loss adjustment expense, or “LAE”). As of December 31, 2025, roughly 55% of our claims were automated, resulting in instant or near-instant processing from start to finish. AI Jim triages and assigns claims he is not authorized to settle, or ones where he identifies concerns, to human claims experts, analyzing each expert's specialty, qualifications, workload, and schedule to determine to whom to assign the claim. Even where human escalation is needed, AI Jim will have done much of the heavy lifting so our team can settle claims and support customers in their hour of need as quickly and smoothly as possible.

The claims process represents the most acute pain point in the insurance experience, and it is where animosity toward the industry is most commonly cultivated. Re-imagining claims for the benefit of the customer, by aligning interests and incentives and by endeavoring to remove friction, hassle, cost, and delays, is therefore a key driver of our leadership in customer satisfaction.

CX.AI is our bot platform built to understand and resolve customer requests without human intervention. Currently, over half of Lemonade’s customer inquiries are handled this way. Customers often require assistance pre- or post-purchase, ranging from coverage questions to making changes to their policy, such as adding a spouse, updating coverage amounts, changing payment methods, or adding newly purchased items. CX.AI uses Natural Language Processing to analyze and understand customers' requests, helping them perform a growing set of tasks.

Our customer-facing technologies, AI Maya, AI Jim, and CX.AI deliver a superior experience at a fraction of the cost, all the while collecting and utilizing far more data than their human counterparts. A similar construct powers the rest of the Company.

Our 'behind the scenes technology' is structured within three proprietary applications: Forensic Graph, Blender, and Cooper.

Forensic Graph utilizes the combined power of behavioral economics, big data, and AI to predict, deter, detect, and block fraud throughout the customer engagement. Insurance fraud is a complicated problem to solve for traditional insurers, mostly due to data paucity. Forensic Graph tracks untold signals and analyzes relationships between things which may appear trivial or invisible to humans, but in which our machine learning uncovers complex multivariate links that have helped us avoid millions of dollars' worth of potential losses.

Blender is a robust insurance management platform that we built with customer centricity and exponential efficiency in mind. This is a built-from-scratch, cutting edge backend system, designed as a single, cohesive, and streamlined management tool for our customer experience, underwriting, claims, growth, marketing, finance, and risk teams. When a claims experience specialist logs in to Blender, for example, they instantly see all claims assigned to them by AI Jim. Blender then provides them with instructions for next steps, and when possible, includes coverage determinations, and alerts of suspicious activity. Critically, they will also see an extraordinary amount of information about the users' behavior patterns and their claim, background information, risk indicators, insurance history, and much more. If a vendor is needed, for example, to assess the damage, all appropriate suppliers will appear in Blender, and can be dispatched to the field, and paid, at the push of a button. Blender brings similar integrated, customer-centric, and focused workflows to the other Lemonade teams as well.

Cooper is our internal bot (we like to think of him as our own Jarvis) who runs important parts of our Company. Cooper handles complex as well as repetitive tasks, from helping our customer experience team handle lengthy, manual processes such as processing paper checks, to automatically running tens of thousands of tests on each release of our software. Cooper continuously analyzes spectrometry imaging beamed from NASA's satellites, identifying wildfires in real time and blocking ads and sales in the affected areas; Cooper collates and formats materials for our regulatory filings; and he even handles most of our engineering task allocation, code deployment, QA, and more. Cooper makes our team dramatically more efficient and keeps evolving and learning with time.

Blender, Forensic Graph and Cooper, together with AI Maya, AI Jim, and CX.AI, run atop our Customer Cortex. The Customer Cortex, like a central nervous system, is the place where all data about our customers is transmitted, continuously analyzed, and then used by all six applications.

We recently passed 3 million customers, proof that people are ready for insurance to work differently. We are well positioned to continue to grow our customer base by continuing to attract first time buyers, an underserved population that continually replenishes.

Our delightful experience and competitive pricing also attract customers who switch from their existing carriers. Our bot automatically files the necessary paperwork to cancel a customer's old policy, removing what is typically a barrier to switching. As we continue to strengthen brand recognition and execute our marketing strategy, we will look to increase the number of customers migrating to the Lemonade platform.

As our customers move up the economic ladder and through lifecycle events, their insurance needs evolve to higher value products: renters typically acquire more property and frequently upgrade to successively larger homes. Growing households often need car, pet, and life insurance, and additional coverage. These progressions regularly trigger orders of magnitude jumps in insurance premiums, and within states that offer all of Lemonade’s “suite of products” - Renters, Home, Car, Pet, and Life - we see a growing proportion of customers with multiple Lemonade policies and see ripe opportunities for the business. For instance, we see a significant opportunity for Lemonade Car in selling to our existing customers, allowing us to acquire customers at little or no cost. Of the approximately 3,000,000 customers we have today, about 1.9 million already have car insurance—that translates to a potential multi-billion dollar opportunity in car premiums at nearly zero acquisition costs. We aim to provide an unmatched user experience in order to retain customers throughout their lifespan, expanding their lifetime value without incurring any incremental costs of acquisition.

Our strategy of growing with our customers also lends itself to expanding into new lines of insurance, as lifecycle events trigger the need for additional insurance products.

Our regulatory framework, technology stack, and brand are all extensible to new lines of insurance, and we anticipate that these will contribute to our growth in the future. In the last five years, we have added life, pet and car insurance to our growing portfolio of offerings, and have expanded product offerings in certain countries in Europe and the UK.

The Lemonade platform is inherently multilingual and agile by design, so that we can efficiently expand into new markets and new product offerings both within the United States and internationally. We are licensed to sell renters, homeowners, pet and/or car insurance policies in 50 states of the United States and Washington, D.C. As of December 31, 2025, we operate in 41 of those states and Washington, D.C., which collectively represent approximately 95% of the U.S. population. Our strong brand and unique business model drive rapid growth and allow us to quickly gain share in new markets. We also hold a pan-European license, enabling us to passport into and sell in 30 countries across Europe. We currently operate in Germany, the Netherlands, France and the UK and will continue to expand our product offerings in other countries.

We offer our products to renters and homeowners in the United States, France, the Netherlands and the UK (in addition to liability insurance) and contents and liability insurance in Germany. The insurance we offer in the United States covers stolen or damaged property, and personal liability, which protects our customers if they are responsible for an accident or damage to another person or their property. In a number of states, we also offer landlord insurance policies to condo and co-op owners who rent out their property less than five times a year.

In the past two years, we expanded our offerings to include Buildings insurance in the UK, the Netherlands and France, giving homeowners the ability to purchase extensive coverage for their home and belongings. Both expansions in the UK and France were supported by existing partnerships with Aviva in the UK and BNP Paribas Cardif in France, providing coverage options unique to each locale through our fully digital experience.

The full Lemonade experience is available through our iOS and Android apps, as well as through our website. Before a customer purchases one of our policies, we allow the customer to review a summary of their coverage and a sample policy. We also enable the customer to reconfigure their coverage and other policy settings, such as the deductible and start date. After payment via a credit or debit card, we instantly issue the customer their policy documents and send it to them via email. From start to finish, the entire process is completed digitally.

In the U.S., our products automatically cover all residents of a household who are related to the customer by marriage, blood, or adoption. In addition to the base coverage we offer for personal property, electronics, furniture, and clothing, our customers can purchase extra coverage to protect against accidental loss, damage, and theft, worldwide, of their jewelry, fine art, and other personal property.

We currently offer pet insurance that covers diagnostics, procedures, medication, accidents or illness. Even our basic pet insurance offering covers blood tests, urinalysis, X-rays, MRIs, lab work, and CT scans. We also offer two optional add-ons to the basic plan, a wellness package and an extended accident and illness package. These provide additional coverage for preventative care costs, including annual exams and vaccines, and recovery treatments, including physical therapy and hydrotherapy.

We believe our expansion into pet insurance will allow us to further achieve our long-term strategy of growing with our young customer base by offering new insurance experiences to customers as they progress in their lifecycles. Our leadership in leveraging AI has also allowed us to create a highly-efficient business. Our Pet book of business has increased more than 35x (in IFP), dropped 39 points from the loss ratio, and increased efficiencies by 78%, driving down the cost per claim from $65 to $14. About 87% of our pet insurance policies were sold to new customers, and about 5% of those have already added a renters or homeowners policy to their pet policy as of December 31, 2025. Customers that bundle our insurance offerings typically save money. The remaining 13% or so of pet insurance policies were sold to existing customers, whose median premium per customer grew roughly 3.8x with little to no incremental customer acquisition costs.

We offer car insurance in a number of states. Lemonade Car insurance covers car accidents, weather damage, theft and vandalism, damage from fire, trees, or animals, glass and windshield repair, liability for bodily injury and property damage, medical expenses, roadside assistance, and reimburses drivers for expenses relating to temporary transportation when a car is being repaired, subject to certain exceptions.

Recently, we have integrated a pricing model in certain markets that utilizes direct vehicle telemetry to distinguish between human-driven and autonomous miles. This allows us to offer specialized rates for self-driving technologies specifically pricing autonomous miles at significant discount to reflect the differing risk profiles of AI-assisted driving.

Lemonade also provides life insurance through a partnership arrangement with a third-party carrier, Legal & General Group. With Lemonade’s term life insurance offering individuals can apply online for up to $1.5 million or more in coverage, for a term of 10 to 40 years. Applicants use Lemonade’s interface to receive an initial quote estimate and then are transferred to our partner to complete their final application.

Giveback is a distinctive Lemonade policy to which the Company continues to have a deep commitment. Each year, we aim to donate funds to cause our customers care about. After our customers purchase a policy, we ask them to select from a list of charitable causes categories to support. We determine the annual Giveback based on our review of the Company’s financial performance and our customers’ chosen causes, and aim to donate funds quarterly.

The Giveback is paid only if payment is authorized by our board of directors in its sole discretion and consistent with its duty of care. See "Risk Factors — We could be forced to modify or eliminate our Giveback, which could undermine our business model and have a material adverse effect on our results of operations and financial condition." Since 2017, we have donated over $12 million to causes chosen by our customers under our Giveback program. The Giveback is not a contractual obligation to any customer or to any cause, and customers may not take a tax deduction related to the donations.

Although a new and untested concept, we believe that donating funds to causes our customers care about will discourage fraud and promote greater trust between us and our customers. The Giveback program, and its underlying ethos, has also helped build an honest relationship with our consumers. They trust us, and they also become part of a community; our policyholders are helping others while protecting their valuables, insuring their home, or making sure their pet can afford vital medical care.

Our goal is to increase brand awareness and the number of customers migrating to our platform by utilizing a number of marketing channels to aid our direct-to-consumer sales model. Our primary channel of advertisement is the internet, where we promote our ads and services through various media and social media platforms, including Facebook, TikTok, YouTube, X and Instagram. We also use the data generated in customer support interactions to constantly refine and improve our marketing campaigns. We conduct drip campaigns via email to follow up with those who have inquired about us or started the onboarding process. Additionally, we enter into agreements with parties who have access to potential customers, including insurance agencies, apartment building owners, and property management companies.

Our digital platform enables us to ask fewer questions of our customers but derive many times more data points from each customer interaction than our competitors. Applying machine learning to these data allows us to identify predictive patterns, and these inform our underwriting. Our underwriting process involves collecting this information, classifying and evaluating each individual risk exposure, assessing the impact of the risk on our existing portfolio, and pricing the risk accordingly.

Our claims process is conducted via our digital platform, which includes our iOS and Android mobile apps. Claims can be substantiated with receipts, notes of where and when the item was purchased, and in certain cases, police reports. We also ask the customer to record a video explaining their claim to enhance the claim review process. After the customer completes a claim report on our mobile app, the customer is asked to enter bank account information. If the claim is approved, a payment is issued and deposited directly into the customer's account. Claims are often paid or declined through our claims bot, AI Jim, within seconds.

While a meaningful portion of simple theft and standard pet claims are paid almost instantly, in many cases the incident is also reviewed by a human before the claim is approved, and certain property damage claims or liability claims may take longer to settle. In an event that requires immediate assistance or temporary housing as a result of fire, ongoing water damage, or structural damage that leaves the customer's home exposed, we contact the customer to assess the situation and provide emergency services, such as water or fire damage cleanup, temporary housing, or a designated specialist.

Insurance companies typically experience highly recurring revenue streams, and hence predictable top lines, but with significant bottom line volatility, as profits can literally fluctuate with the weather. Earthquakes, hailstorms, wildfires and hurricanes strike with caprice, and can push an otherwise profitable business deep into the red with little or no warning.

The first-order consequence of this uncertainty is that insurers often see unwelcome swings in their results. The second-order consequence is that regulators require insurers to keep significant reserves to absorb these swings, making them capital intensive. We set out to architect our business to be at once capital-light and possessed of a predictable and growing gross margin. Through judicious use of "reinsurance," we believe we have largely achieved these goals.

Reinsurance is a financial instrument under which one insurer, the "reinsurer," agrees to cover a portion of the claims of another insurer, the "primary insurer," in return for a portion of their premiums. While this description characterizes all reinsurance, implementations come in different flavors, each with its own costs and benefits. We have entered into a range of reinsurance agreements, differing in both duration and terms, which combine, we believe, to deliver maximum capital efficiency, while optimizing our gross margin for both stability and size.

The low cost of capital for reinsurance companies creates an opportunity to share premiums and maintain our gross margin while reducing our capital requirements. We maintain proportional reinsurance contracts which transfers, or “cedes”, a specified percentage of the premium to reinsurers (“Proportional Reinsurance Contracts”).

Under U.S. and E.U. regulatory laws, insurance companies are required to set aside "surplus capital" in accordance with various formulae. Our proportional reinsurance structure shifts much of that surplus capital requirement to the reinsurer, reducing these capital requirements.

As described above, our Proportional Reinsurance Contracts provide that we cede a portion of our premiums to our reinsurers, improving our capital efficiency. We manage the remaining portion of our business with alternative forms of reinsurance, with a view to maximizing profitability.

These two remaining goals live in tension with one another: leaving zero "wiggle room" around our fixed fee would guarantee its stability, but would diminish the benefit from an improved loss ratio. Conversely, any room for improved profitability would also introduce additional volatility.

To balance our desire for both growing and stable gross margin, we set out to structure our remaining reinsurance such that variability in our gross margin is reduced, though not eliminated entirely. We believe we have achieved this through a combination of reinsurance structures known as "per risk reinsurance" (the "Non-Proportional Reinsurance Contracts"), which together reduce the maximum amount we would need to pay for any one claim.

Our business is exposed to the risk of severe weather conditions and other catastrophes which are inherently unpredictable. To reduce this risk, we also purchase a catastrophe excess of loss policy with a one year term.

We formed a risk-bearing entity, Lemonade Re SPC, in the Cayman Islands, where we hold some of our retained risk. We also established a captive cell facility at a Bermuda transformer vehicle that is authorized to write and purchase insurance / reinsurance where we retain most of our tail catastrophe exposure.

We believe our reinsurance structure achieves these important goals: making us capital-light, buffering our gross margin from the vicissitudes of claims, and leaving room for our gross margin to grow.

Our book of business was reinsured approximately 55% through June 30, 2025 and approximately 20% through June 30, 2026, under agreements renewed and renegotiated on an annual basis. The Proportional Reinsurance Contracts with a term of one year that expires on June 30, 2026 are issued by Hannover Ruck SE and MAPFRE Re Compania De Reaseguros S.A., each holding an ‘A’ or better rating from A.M. Best, and each holding a share of the agreement’s commitments. In addition, Lemonade Insurance Company (LIC) and Metromile Insurance Company (“MIC”) cedes approximately 15% and 35% of their premiums and losses, respectively, to our Cayman Islands-based captive reinsurer.

Our Non-Proportional Reinsurance Contracts are issued by a collection of reinsurers, each holding an ‘A’ or better rating from A.M. Best, and have a one-year term that expires on June 30, 2026. We also have a reinsurance contract between LIC and MIC, and a Bermuda-based segregated cell insurer to cover catastrophe risks over the initial $50,000,000 limit for each loss occurrence, and further subject to a limit of $80,000,000 for each loss occurrence and in aggregate.

We believe that the terms of our reinsurance arrangements provide an appropriate balance between maximizing predictability, and enabling us to capture more margin over time.

Our portfolio of investable assets is primarily held in cash, money market funds, and fixed income securities which include U.S. and non-US government and government agency obligations, corporate debt securities and asset-backed securities of relatively short durations. We manage the portfolio in accordance with investment policies and guidelines approved by our board of directors.

We have designed our investment policy and objectives to provide a balance between current yield, conservation of capital, and liquidity requirements of our operations, setting guidelines that provide for a well-diversified investment portfolio that is compliant with insurance regulations applicable to the states in which we operate. Furthermore, our investment policy prohibits investments in sectors such as oil and gas, coal, tobacco, controversial weapons, and entities that exhibit non-compliance with the United Nations Global Compact. The policy, which may change from time to time, is approved by the board of directors and is reviewed on a regular basis to ensure that the policy evolves in response to changes in the financial markets and our risk profile. See "Note 4 — Summary of Significant Accounting Policies" in the Notes to Consolidated Financial Statements included in this Annual Report.

The homeowners, pet, car and, to a lesser extent, the renters insurance industries in which we operate are highly competitive. While we believe we are well positioned to execute our business model and reinvent insurance, we face significant competition from traditional insurance companies such as Allstate, Farmers, Liberty Mutual, State Farm, GEICO, Progressive and Travelers. Although we are tapping into markets that our competitors have struggled to reach, the incumbent insurance companies are larger than us and have significant competitive advantages over us, including increased name recognition, higher financial ratings, greater resources, additional access to capital. In particular, many of these competitors offer consumers the ability to purchase homeowners and multiple other types of insurance products and "bundle" them together, and in certain circumstances, to include an umbrella liability policy for additional coverage at competitive prices. Moreover, as we expand into new lines of business and offer additional products beyond renters and homeowners insurance, pet and car insurance, we may face intense competition from traditional insurance companies that are already established in such markets. Competitors in the pet insurance space include companies such as Nationwide, Embrace, and Trupanion. Competitors in the car insurance space include companies such as Progressive, GEICO and Allstate.

We also compete with new market entrants. Competition is based on many factors, including the reputation and experience of the insurer, coverages offered, pricing and other terms and conditions, customer service, relationships with brokers and agents (including ease of doing business, service provided, and commission rates paid), size, and financial strength ratings, among other considerations. We believe we compete favorably across many of these factors, and have developed a digital platform and business model based on artificial intelligence and behavioral economics that we believe will be difficult for incumbent insurance providers to emulate.

The protection of our technology and intellectual property is an important aspect of our business. We intend to rely upon a combination of trademarks, trade secrets, copyrights, confidentiality procedures, contractual commitments, and other legal rights to establish and protect our intellectual property. We generally enter into confidentiality agreements and invention of work product assignment agreements with our employees and consultants to control access to, and clarify ownership of, our proprietary information.

As of December 31, 2025, we have 5 issued patents in the United States. The issued patents generally relate to determining the route and parking location of a vehicle, recording trip data associated with a vehicle, and estimating the usage of a vehicle based on refueling events. The issued patents will expire between September 1, 2035 and January 11, 2036. We do not own any foreign patents and do not have any foreign patent applications pending. As of December 31, 2025, we hold 137 foreign registered trademarks and 8 registered trademarks in the United States, including the Lemonade and Metromile marks, and have no foreign trademark applications pending and no U.S. trademark applications pending. We also hold 3 copyrights in the United States, covering certain videos, texts, photographs, and artwork displayed on our mobile apps and website. We continually review our development efforts to assess the existence and patentability of intellectual property.

Intellectual property laws, procedures, and restrictions provide only limited protection and any of our intellectual property rights may be challenged, invalidated, circumvented, infringed, or misappropriated. Further, the laws of certain countries do not protect proprietary rights to the same extent as the laws of the United States, and, therefore, in certain jurisdictions, we may be unable to protect our proprietary technology.

While not required by Delaware law or the terms of our certificate of incorporation, we have been designated as a Certified B Corp. The term "Certified B Corp" does not refer to a particular form of legal entity, but instead refers to companies that are certified by B Lab, an independent nonprofit organization, as meeting rigorous standards of social and environmental performance, accountability, and transparency.

The first step in becoming a Certified B Corp is completing a comprehensive and objective assessment of a business's positive impact on society and the environment. The assessment varies depending on the company's size (number of employees), and sector. The standards in the assessment are created and revised by an independent governing body that determines eligibility to be a Certified B Corp.

Based on responses to a set of over 200 questions that reflect impact indicators, best practices, and outcomes, a company receives a composite score on a 200-point scale representative of its overall impact on its employees, customers, communities, and the environment. Representative indicators in the assessment range from payment of living wage, employee benefits, charitable giving/community service, and use of renewable energy.

Recognition as a Certified B Corp currently requires that a company achieve a reviewed assessment score of at least 80. The review process includes a phone review and a random selection of indicators for purposes of verifying documentation. The assessment also includes a corporate structure review and a disclosure questionnaire, including certain practices, fines, and sanctions related to the company or its partners.

Our certification also required us to adopt the public benefit corporation structure, a step we have already completed. Once certified, every Certified B Corp must make its assessment score transparent on the independent non-profit organization's website. Acceptance as a Certified B Corp and continued certification is at the sole discretion of the independent nonprofit organization.

As of December 31, 2025, we had 1,282 employees, 810 of whom were based in the United States and the rest of whom were based outside of the United States, primarily in Israel and the Netherlands. In the Netherlands, certain employees are subject to a collective agreement between the Dutch Association of Insurers and various trade unions. The collective agreement covers wages and terms and conditions of employment. Participation in the collective agreement is mandatory for members of the Dutch Association of Insurers, a leading association of private insurance companies operating in the Netherlands. Beyond this, to our knowledge, none of our employees are represented by a labor union. We consider our relationships with our employees to be good and have not experienced any interruptions of operations due to labor disagreements.

As of December 31, 2025, and based on public information from five competing insurance companies in the United States, we estimate that the number of customers per employee for those companies ranges from approximately 300 to approximately 600 customers per employee. We base this estimate on publicly available information, which we have adjusted for comparability. The calculation of "employees" includes insurance agents and brokers because they are a significant cost component for other insurance companies. In comparison to these competitors, our number of customers per employee was approximately 2,300 as of December 31, 2025.

Our status as a Certified B Corp and our commitment to charitable giving, in particular our Giveback program, distinguishes us from our competitors, with the goal of building a trusting relationship between us, our employees, and our customers. We value the power of creativity and encourage and support the sharing of ideas to enhance our business model. Like the industry in which we operate, we understand the importance and value of a community pooling its resources together for the public good. We value inclusivity, respecting differences, and seamless teamwork in every facet of our business.

We issued 500,000 shares of common stock in 2020 as the initial endowment of the Lemonade Foundation, a 501(c)(4) social welfare organization established under Arizona law. By contributing approximately 1% of our common stock to the Lemonade Foundation, we hope to promote charitable giving and other community-centric activities with a nexus to our community.

In 2023, the Foundation, launched a first of its kind blockchain-based insurance product benefitting some of the world’s most vulnerable farmers. The product was built with a goal of protecting subsistence farmers against the effects of climate variability. Thousands of families in Kenya have already been protected by this product, and the Foundation expects to continue scaling this product in the coming years. The product was launched as part of the Lemonade Foundation Crypto Climate Coalition - in cooperation with a number of strategic partners, including Hannover Re, Pula, Chainlink, Avalanche, Etherisc and DAOstack.

We understand that strength lies in the unique backgrounds of our employees that drive the innovation behind our product. We encourage employees to bring their lived experiences, and personal strengths, to develop new ideas, improve customer experiences and shape our brand. We engage with employees for ideas of nonprofits to partner with, or resources to learn more about a social issue, and their candid (and anonymous, should they choose) feedback about our workplace culture and environment. Additionally, our employees organize several education groups across the Company addressing these important topics.

As a B Corp, it is part of our legal mission to advance the health and well-being of employees. To that end, employees have access to health and wellness programs, and healthcare plans.

In the United States, as of December 31, 2025, LIC and MIC are licensed to sell our insurance products in the following states:

We also hold a pan-European license, which enables us to sell in 30 countries across Europe, and currently operate and sell our insurance products in Germany, the Netherlands, France and the UK.

For information regarding the seasonality of our business, please refer to Part II, Item 7 “Management’s Discussion and Analysis of Financial Condition and Results of Operations” of this Annual Report.

Our U.S. insurance subsidiaries are regulated by insurance regulatory authorities in the states in which we operate. State insurance laws and regulations generally are designed to protect the interests of customers, consumers, and claimants rather than stockholders or other investors. State regulators generally have broad administrative power with respect to all aspects of the insurance business. The regulatory requirements and restrictions include, among others, the following:

•approval of policy forms and premium rates;

•approval for intercompany service agreements;

•advertising, marketing, and trade practices; and

•restrictions on the ability of our regulated insurance subsidiaries to pay dividends to us or enter into certain related party transactions

Regulation of insurance companies constantly changes as governmental agencies and legislatures react to real or perceived issues.

Our regulated U.S. insurance subsidiaries are domiciled and admitted in the states of New York and Delaware. Under a provision of the California Insurance Code, MIC is deemed “commercially domiciled” in California, meaning that the California Department of Insurance is entitled to regulate certain aspects of MIC’s business as if it were actually domiciled in California.

LIC, MIC, Lemonade Insurance Agency, LLC, Lemonade Life Insurance Agency, LLC, Lemonade E&S Insurance Agency, LLC and Metromile Insurance Services LLC must apply for and maintain licenses to provide and sell insurance in those jurisdictions in which they transact insurance businesses.

Our insurance company and insurance producer subsidiaries are required to adhere to myriad laws and regulatory requirements. The insurance regulators in the states in which our subsidiaries do the business of insurance are empowered to conduct on-site visits and examine the financial affairs and market conduct practices of those entities. Insurance regulators have broad administrative powers to impose monetary penalties and/or restrict or revoke licenses to transact business for violations of applicable laws and regulations.

We are a holding company that transacts a majority of our business through operating subsidiaries. Consequently, our ability to pay dividends to stockholders and meet our debt payment obligations is largely dependent on dividends and other distributions from our subsidiaries. Applicable insurance laws restrict the ability of our regulated insurance subsidiaries to declare stockholder dividends. Applicable insurance regulators require insurance companies to maintain specified levels of statutory capital and surplus.

Insurance regulators have broad powers to prevent reduction of statutory surplus to inadequate levels, and there is no assurance that dividends of the maximum amounts calculated under any applicable formula would be permitted to be made by our insurance subsidiaries. State insurance regulatory authorities that have jurisdiction over the payment of dividends by our regulated insurance subsidiaries may in the future adopt statutory provisions more restrictive than those currently in effect.

LIC is subject to New York’s insurance laws and MIC is subject to Delaware and California’s laws regarding the composition of their investments. Those laws generally require diversification of their investment portfolios and limits on the amount of their investments in certain categories. Failure to comply with these laws and regulations would cause non-conforming investments to be treated as non-admitted assets for purposes of measuring statutory surplus and, in some instances, would require those companies to sell those investments.

In most states in which we operate, insurance claims adjusters are required to be licensed and some must fulfill annual continuing education requirements. In most instances, our employees who are negotiating coverage terms are underwriters and are not required to be licensed agents. As of December 31, 2025, 382 employees were required to maintain and did maintain requisite licenses for these activities as required by the states in which we operate.

The National Association of Insurance Commissioners (“NAIC”) has engaged in a concerted effort to strengthen the ability of U.S. state insurance regulators to monitor U.S. insurance holding company groups. Among other things, the NAIC’s model, when adopted, requires the ultimate controlling person of an insurance company to submit an annual enterprise risk management report that describes the risk that an activity, circumstance, event, or series of events involving one or more affiliates of an insurer will, if not remedied promptly, be likely to have a material adverse effect upon the financial condition or liquidity of the insurer or its insurance holding company system as a whole. Recently, the NAIC has developed model laws requiring annual reports concerning the nature of corporate governance within an insurance holding company.

The NAIC in 2012 adopted the Risk Management and Own Risk and Solvency Assessment (“ORSA”) Model Act (the “ORSA Model Act”) to require domestic insurers to maintain a risk management framework and establishes a legal requirement for domestic insurers to conduct an ORSA in accordance with the NAIC’s ORSA Guidance Manual. The ORSA Model Act provides that domestic insurers, or their insurance group, must regularly conduct an ORSA consistent with a process comparable to the ORSA Guidance Manual process. The ORSA Model Act also provides that, no more than once a year, an insurer’s domiciliary regulator may request that an insurer submit an ORSA summary report, or any combination of reports that together contain the information described in the ORSA Guidance Manual, with respect to the insurer and the insurance group of which it is a member. When the ORSA Model Act is adopted by a particular state, it imposes more extensive filing requirements on parents and affiliates of domestic insurers. Delaware and New York have adopted the ORSA Model Act.

In the course of our business, we collect and maintain confidential and personal information. As a result, we are subject to U.S. federal and state and international privacy and data security laws and regulations that, among other things, require that we institute and maintain certain policies and procedures to safeguard this information from improper use or disclosure. For example, in 2017, the New York Department of Financial Services (“NY DFS") adopted a broad cybersecurity regulation that requires financial services institutions to, among other things, implement and maintain a cybersecurity program and a cybersecurity policy that will be monitored and tested periodically, develop controls and technology standards for data protection, meet minimum standards in response to any cybersecurity breach and annually certify their compliance with the regulation. The NY DFS in 2023 issued a significant amendment to the cybersecurity requirements, mandating that covered entities adopt specific standards and controls to secure sensitive data. The recent amendment significantly expands obligations of entities regulated by NY DFS to report cybersecurity incidents and enhance their consumer data protection and cybersecurity infrastructure. Regulated entities were generally required to comply with the new requirements imposed by the Amendment in phases throughout 2024 and 2025.

The NAIC in 2017 adopted the Insurance Data Security Model Law, which established standards for data security and for the investigation and notification of insurance commissioners of cybersecurity events involving unauthorized access to, or the misuse of, certain nonpublic information. Many states have enacted the Insurance Data Security Model Law or similar laws, and we expect more states to follow.

Additionally, a growing set of privacy regulations have created intense scrutiny by legislative, regulatory, and self-regulatory bodies, privacy advocates, academics, and commercial interests in the United States and abroad that focus on consumer data protection and privacy regarding interest-based advertising, or the use of data to draw inferences about a consumer’s interests and deliver relevant advertising to that consumer. In particular, much of this scrutiny has focused on the use of cookies and other tracking technologies that collect or aggregate information about consumers’ online browsing and mobile app usage activity. It is essential that we monitor legal requirements and other developments in this area, domestically and globally, maintain a robust privacy and security compliance program, and engage in responsible privacy practices, including providing consumers with notice of the types of data we collect, how we collect it, with whom we share it, how we use that data to provide our solutions, and the applicable choices we offer consumers.

California has enacted legislation restricting the use of automated systems to communicate with people online. California enacted a statute making it unlawful for any person to use a bot to communicate with another person in California online with the intent to mislead the other person about its artificial identity for the purpose of knowingly deceiving the person about the content of the communication in order to incentivize a purchase or sale of goods or services in a commercial transaction. The statute provides that a person using a bot will not be liable under the statute if the person discloses that it is a bot. See “Risk Factors — Risks Relating to Our Business — New legislation or legal requirements may affect how we communicate with our customers, which could have a material adverse effect on our business model, financial condition, and results of operations.”

The General Data Protection Regulation (E.U.) 2016/679 (the “E.U. GDPR”) applies to our activities to the extent that those activities take place in the context of our establishments in the European Union, and the UK General Data Protection Regulation and Data Protection Act 2018 (collectively, the “UK GDPR”) applies to our activities to the extent that those activities take place in the context of our establishments in the UK (EU GDPR and UK GDPR together referred to as the “GDPR”). In addition, the GDPR may apply to our activities that involve the processing of personal data of individuals in the European Union or UK to whom we offer our products or services. The GDPR could also apply to our business if we were to monitor the activities of individuals in the European Union or UK. As we expand into Europe or UK, the compliance obligations under the GDPR will become more significant. See “Risk Factors — Risks Relating to Our Business — We may face particular privacy, data security, and data protection risks as we continue to expand into Europe and the UK. in connection with the GDPR and other data protection regulations.”

A number of federal laws affect and apply to the insurance industry, including various privacy laws, the Fair Credit Reporting Act (“FCRA”), and the economic and trade sanctions implemented by the Office of Foreign Assets Control (“OFAC”) of the U.S. Department of the Treasury. OFAC maintains and enforces economic sanctions against certain foreign countries and groups and prohibits U.S. persons from engaging in certain transactions with certain persons or entities. OFAC has imposed civil penalties on persons, including insurance and reinsurance companies, arising from violations of its economic sanctions program.

State insurance laws permit U.S. insurance companies, as ceding insurers, to take financial statement credit for reinsurance that is ceded, so long as the assuming reinsurer satisfies the state’s credit for reinsurance laws. There are several different ways in which the credit for reinsurance laws may be satisfied by an assuming reinsurer, including being licensed in the state, being accredited in the state, or maintaining certain types of qualifying collateral. We ensure that LIC and MIC are able to take full financial statement credit for their reinsurance.

Most states require admitted property and casualty insurance companies to become members of insolvency funds or associations which generally protect customers against the insolvency of the admitted insurance companies. Members of the fund or association must contribute to the payment of certain claims made against insolvent insurance companies through annual assessments. The annual assessments required in any one year will vary from state to state, and are subject to various maximum assessments per line of insurance.

In January 2025, the Greater Los Angeles area experienced significant wildfires (the “January 2025 California Wildfires”). The Company incurred net losses of approximately $19.6 million related to these events. Additionally, the Company received a $6.9 million assessment from the California FAIR Plan in February 2025, which was paid and expensed in the first quarter of 2025. The Company received regulatory approval for recoupment of up to 50% of the assessment over a period of two years beginning in 2026. See “Risk Factors - Our exposure to loss activity and regulation may be greater in states where we currently have most of our customers: California, New York and Texas.” and “Management's Discussion and Analysis” for additional information.

Risk-based capital laws are designed to assess the minimum amount of capital that an insurance company needs to support its overall business operations and to ensure that it has an acceptably low expectation of becoming financially impaired. State insurance regulators use risk-based capital ratios to set capital requirements, considering the size and degree of risk taken by the insurer and taking into account various risk factors including asset risk, credit risk, underwriting risk, and interest rate risk. As the ratio of an insurer’s total adjusted capital and surplus decreases relative to its risk-based capital, the risk-based capital laws provide for increasing levels of regulatory intervention culminating with mandatory control of the operations of the insurer by the domiciliary insurance department at the so-called mandatory control level. Our regulators in New York, Delaware and California require annual reporting to confirm that LIC and MIC hold in excess of the minimum amount of risk-based capital necessary for their operations. Insurers falling below a calculated threshold may be subject to varying degrees of regulatory action. Failure to maintain risk-based capital at the required levels could adversely affect the ability of LIC and MIC to maintain the regulatory approvals necessary to conduct their businesses. As of December 31, 2025, LIC maintained a risk-based capital level of 586% and MIC maintained a risk-based capital level of 625%.

The NAIC Insurance Regulatory Information System (“IRIS”) is a collection of analytical tools designed to provide state insurance regulators with an integrated approach to screening and analyzing the financial condition of insurance companies operating in their respective states. IRIS consists of two phases: statistical and analytical. In the statistical phase, the NAIC database generates key financial ratio results based on financial information obtained from insurers’ annual statutory statements. The statistical phase highlights those insurers that merit the highest priority in the allocation of the state insurance regulators’ resources. The ratios are not, in themselves, indicative of adverse financial conditions. The analytical phase is a review of the annual statements, financial ratios, and other automated solvency tools. An insurance company may fall out of the usual range for one or more ratios for any number of reasons and a ratio falling outside the prescribed "usual range" is not considered a failing result. Rather, unusual values are viewed as part of the regulatory early monitoring system. The primary goal of the analytical phase is to identify companies that appear to require immediate regulatory attention.

Statutory accounting principles (“SAP”) is a basis of accounting developed by U.S. insurance regulators to monitor and regulate the solvency of insurance companies. In developing SAP, insurance regulators were primarily concerned with evaluating an insurer’s ability to pay all its current and future obligations to customers. As a result, statutory accounting focuses on conservatively valuing the assets and liabilities of insurers, generally in accordance with standards specified by the insurer’s domiciliary jurisdiction. Uniform statutory accounting practices are established by the NAIC and generally adopted by regulators in the various U.S. jurisdictions. These accounting principles and related regulations determine, among other things, the amounts our regulated insurance subsidiaries may pay to us as dividends and differ somewhat from U.S. Generally Accepted Accounting Principles (“GAAP”), which are designed to measure a business on a going-concern basis. GAAP gives consideration to matching of revenue and expenses and, as a result, certain expenses are capitalized when incurred and then amortized over the life of the associated policies. The valuation of assets and liabilities under GAAP is based in part on best estimate assumptions made by the insurer. Stockholders’ equity represents both amounts currently available and amounts expected to emerge over the life of the business. As a result, the values for assets, liabilities, and equity reflected in financial statements prepared in accordance with GAAP may be different from those reflected in financial statements prepared under SAP.

Nearly all states have insurance laws requiring personal property and casualty insurers to file rating plans, policy or coverage forms, and other information with the state’s regulatory authority. In many cases, such rating plans, policy forms, or both must be approved prior to use.

The speed with which an insurer can change rates in response to competition or increasing costs depends, in part, on whether the rating laws are (i) prior approval, (ii) file-and-use, or (iii) use-and-file laws. In states having prior approval laws, the regulator must approve a rate before the insurer may use it. In states having file-and-use laws, the insurer does not have to wait for the regulator’s approval to use a rate, but the rate must be filed with the regulatory authority prior to being used. A use-and-file law requires an insurer to file rates within a certain period of time after the insurer begins using them. Eighteen states, including California and New York, have prior approval laws. Under all three types of rating laws, the regulator has the authority to disapprove a rate filing.

An insurer’s ability to adjust its rates in response to competition or to changing costs is dependent on an insurer’s ability to demonstrate to the regulator that its rates or proposed rating plan meets the requirements of the rating laws. In those states that significantly restrict an insurer’s discretion in selecting the business that it wants to underwrite, an insurer can manage its risk of loss by charging a rate that reflects the cost and expense of providing the insurance. In those states that significantly restrict an insurer’s ability to charge a rate that reflects the cost and expense of providing the insurance, the insurer can manage its risk of loss by being more selective in the type of business it underwrites. When a state significantly restricts both underwriting and pricing, it becomes more difficult for an insurer to maintain its profitability.

From time to time, the personal lines insurance industry comes under pressure from state regulators, legislators, and special interest groups to reduce, freeze, or set rates at levels that do not correspond with our analysis of underlying costs and expenses. We expect this kind of pressure to persist. State regulators may interpret existing law or rely on future legislation or regulations to impose new restrictions that adversely affect profitability or growth. We cannot predict the impact on our business of possible future legislative and regulatory measures regarding insurance rates.

Our European insurance entities consist of Lemonade Insurance N.V., Lemonade Agency B.V., their respective UK branch undertakings, and Lemonade B.V.. We also establish and maintain an entity for the provision of intercompany support services; Lemonade Technology B.V.. Lemonade Insurance N.V. is a licensed non-life insurer established in the Netherlands and is subject to key financial rules and regulations including the Second European Solvency Directive 2009/138/EC (as amended, the “Solvency II Directive”); Commission Delegated Regulation (EU) 2015/35 (as amended, the “Delegated Regulation”, together with the Solvency II Directive referred to as the “Solvency II Regulations”); the implementing technical standards and regulatory technical standards issued by the European Insurance and Occupational Pensions Authority (“EIOPA”); the European Insurance Distribution Directive (Directive (EU) 2016/97, “IDD”); the Dutch Financial Supervision Act (Wet op het financieel toezicht, “DFSA”) and the lower rules and regulations promulgated thereunder; the International Financial Reporting Standards as adopted by the European Union ("IFRS EU"); and national regulations, as well as local conduct of business requirements, in each of the jurisdictions in which it operates. Currently, the European Commission is preparing for a review of the Solvency II Directive. Lemonade Agency B.V. is subject to the IDD, the DFSA and national regulations, as well as local business conduct requirements and consumer laws, in each of the jurisdictions in which it operates. Lemonade B.V. is an insurance holding company within the meaning of article 212 of the Solvency II Directive, as implemented in article 1:1 DFSA.

In addition to the regulations noted above, we are also subject to the European Accessibility Act (Directive (EU) 2019/882, the “EAA”), a landmark directive establishing common accessibility requirements for a range of products and services across the EU, including those related to financial services, e-commerce, and information technology. The EAA mandates accessibility standards to ensure that our digital products and customer service channels are accessible to people with disabilities and our operations and customer-facing technologies meet these mandatory standards.

Lemonade has operated in the UK market since 2022 and is therefore also subject to relevant UK regulation including the Financial Services and Markets Act 2000 (the “FSMA”), the Insurance Act 2015, and relevant subsidiary regulations. By virtue of its authorisation and oversight by both the Prudential Regulation Authority (the “PRA”) and the Financial Conduct Authority (the “FCA”) in the UK, Lemonade is also subject to the regulatory requirements of the PRA Rulebook and the FCA Handbook respectively as they pertain to Insurers, distributing agents and financial service providers generally.

The Solvency II Directive, as implemented in the DFSA and other national regulations, such as the German Insurance Supervisory Act (Versicherungsaufsichtsgesetz), prescribes uniform rules for insurers and their activities and services. More specifically, the Solvency II Directive provides rules and regulations relating to, inter alia, Lemonade Insurance N.V.’s authorization requirements (including the European “passport” regime), its minimum own funds and solvency and its governance. Governance requirements include the need to ensure sound business operations, implement mandatory key functions (including Actuarial, Compliance, Internal Audit and Risk) and requirements relating to Lemonade Insurance N.V.’s Management Board members, Supervisory Board Members and other key personnel. The Delegated Regulation is promulgated under the Solvency II Directive and provides detailed requirements relating to some of the Solvency II Directive’s broader requirements.

The IDD provides a harmonized regime for insurance distribution activities. It regulates the way insurance products are designed and sold both by insurance intermediaries (e.g. Lemonade Agency B.V.) and directly by insurance undertakings (e.g. Lemonade Insurance N.V.). The rules and regulations set out in the IDD have been implemented in the DFSA. The provisions set out in the IDD mainly relate to standards of product disclosure, promotional materials and product governance and oversight. Local regulations and conduct of business rules implemented in each of the European member states in which both Lemonade Agency B.V. and Lemonade Insurance N.V. do business supplement the requirements set out in the IDD.

Lemonade Insurance N.V. is subject to primary supervision by the Dutch Central Bank (De Nederlandsche Bank, “DNB”) as the supervisory authority of its home member state. In addition, it is subject to supervision by the Dutch Authority for the Financial Markets (Autoriteit Financiële Markten, “AFM”). The AFM is the regulator tasked with conduct supervision relating to Lemonade Insurance N.V.’s Dutch activities. The German Federal Financial Supervisory Authority (Bundesanstalt für Finanzdienstleistungsaufsicht, “BaFin”), as the supervisory authority of a host member state. BaFin is the competent regulator tasked with the supervision of Lemonade Insurance N.V.’s compliance with German regulations and conduct requirements. The French Autorité de Contrôle Prudentiel et de Résolution ("ACPR"), which is charged with preserving the stability of the financial system and protecting the customers, insurance policyholders, members and beneficiaries of the persons that it supervises, and Organisme pour le Registre des Intermédiaires en Assurance ("ORIAS"), an association under the supervision of the Treasury Department in France and in charge of approving insurance intermediaries operating on the French market; the Bank of England’s Prudential Regulation Authority in charge of prudentially regulating and supervising financial services firms operating in the UK; the British Financial Conduct Authority, whose role includes protecting consumers, keeping the industry stable, and promoting healthy competition between financial service providers.

Lemonade Agency B.V. is subject to supervision by the AFM. Lemonade B.V., as parent, and Lemonade Insurance N.V., as subsidiary, is an E.U. sub-group within the meaning of Article 213(2)(b) of Solvency II, as implemented in article 3:285 (2) DFSA. Lemonade B.V. is subject to group supervision by DNB under the Solvency II Directive. The relevant EU supervisory body for insurers, EIOPA, has limited supervisory powers in the Netherlands, however it plays an important role in drafting and issuing technical standards and preparing guidance relating to various European directives and regulations. EIOPA aims to accomplish efficient and harmonized financial supervision across the European Union.

DNB and AFM employ a risk-based and proportionate approach to supervision, comprising a firm systemic framework, which focuses on the continuous assessment of how firms manage the risks they create and identifying the root causes of risk. DNB regularly proactively contacts insurers to discuss matters of strategy, day-to-day operations and the current (and expected future) financial standing of the undertaking, in order to assess what parts of a regulated undertaking, if any, could pose systemic risks. In addition, DNB monitors operations and business through monthly updates, the submission of Quantitative Reporting Templates, by reviewing annual reports, approving prospective Management Board and Supervisory Board members prior to their appointment and through scheduled and unannounced audits.

DNB also regulates the acquisition and increase of control over certain authorized firms, including insurers. Under the DFSA, any person intending to acquire control of, or increase (or decrease) control over, an insurer must first obtain the consent of the DNB. In considering whether to grant or withhold its approval for the acquisition of control, DNB must be satisfied that the acquirer is a fit and proper person and that the interests of consumers would not be threatened by their acquisition of, or increase in, control. A person will be treated as increasing (or decreasing) their control over an insurer if the level of their percentage of (indirect) shareholding or voting power in the insurer crosses the 10, 20, 33, 50 percent or 100 percent thresholds.

Both Lemonade Insurance N.V. and Lemonade Agency B.V. commenced operations in the UK under the Temporary Permission Regime in accordance with which certain European Economic Area based firms may continue to operate in the UK for a limited period following the UK's departure from the European Union. During 2023, the UK branch establishments of Lemonade Insurance N.V., and Lemonade Agency B.V. (“UK branch establishments”) received a third country branch authorization in the UK allowing both companies to continue to operate in the UK market on a permanent basis. Lemonade Agency B.V., UK Branch (BR024862) is the UK establishment of Lemonade Agency B.V.. Lemonade Insurance N.V., UK branch (BR025196), is the UK establishment of Lemonade Insurance N.V.. See Required Licensing section below for a description.

DNB and AFM expect firms to avoid actions that jeopardize compliance with their statutory objectives and applicable rules and regulations and have extensive powers to intervene in the affairs of a regulated firm. When DNB is concerned that an insurer may present a risk, this may lead to negative consequences, including the requirement to maintain a higher level of regulatory capital (via capital “add-ons” under the Solvency II Directive) to match the higher perceived risks and enforcement action where the risks identified breach applicable rules and regulations. In case of a breach of our license requirements or obligations arising from the applicable rules and regulations, although both DNB and AFM must apply the principle of proportionality in all of their actions, the regulators have a large amount of discretion in determining what measures to impose, if any, in order to address, remedy, or sanction the breach. DNB and the AFM have a large amount of enforcement tools at their disposal to sanction breaches of applicable rules and regulations, including public formal warnings, orders to adopt a certain course of conduct, incremental penalties, and administrative fines. In addition, breaches may lead to a revocation of an undertaking license and, in the case of insurers, where the breach relates to material prudential shortcomings, DNB may impose emergency measures, including the appointment of an administrator or the imposition of measures aimed at winding-up the undertaking).

Our subsidiary Lemonade Insurance N.V. is licensed and supervised by the insurance supervision division of DNB as a Solvency II non-life insurance company. DNB, as the supervisory authority of its home member state, has permitted us to sell in other European countries, such as Germany and France, on a Freedom of Services basis. In general, in addition to continuing to meet the threshold conditions to authorization, Lemonade Insurance N.V. and Lemonade Agency B.V. are obliged to comply with European regulations, European directives (in as far as these directives have direct effect in the Netherlands or other European member states in which our subsidiaries do business), the DFSA and the lower regulations set out thereunder, and other national regulations, all of which contain detailed rules covering, among other things, systems and controls, conduct of business, and prudential (i.e. capital and solvency) requirements.

Lemonade Insurance N.V. launched its first product in the UK market in October 2022, and operates in the UK through its registered branch establishment, Lemonade Insurance N.V., UK Branch (BR025196) which received third-country branch authorization from the Prudential Regulation Authority in the UK in May 2023. This allows the company to operate in the UK market permanently. Lemonade Insurance N.V. is licensed as an insurance company by De Nederlandsche Bank in the Netherlands (R162036). Authorized by the Prudential Regulation Authority. Subject to regulation by the Financial Conduct Authority and limited regulation by the Prudential Regulation Authority (FRN 846181).

Lemonade Agency B.V. commenced operations in the UK under the TPR as described above, and received third country branch authorisation through its registered branch establishment Lemonade Agency B.V., UK Branch (BR024862) in 2023. Lemonade Agency B.V., UK Branch is authorised and regulated by the Financial Conduct Authority (FRN: 989294).

Our internet website address is www.lemonade.com. In addition to the information about us and our subsidiaries contained in this Annual Report, information about us can be found on our website. Our website and information included in or linked to our website are not part of this Annual Report.

Our annual reports on Form 10-K, quarterly reports on Form 10-Q, current reports on Form 8-K and amendments to those reports filed or furnished pursuant to Section 13(a) or 15(d) of the Securities Exchange Act of 1934, as amended, are available free of charge through our website as soon as reasonably practicable after they are electronically filed with or furnished to the Securities and Exchange Commission (the “SEC”). Additionally, the SEC maintains an internet site that contains reports, proxy and information statements and other information at www.sec.gov.

We have not been profitable since our inception in 2015 and had an accumulated deficit of $1,464.3 million and $1,298.8 million as of December 31, 2025 and December 31, 2024, respectively. We incurred net losses of $165.5 million and $202.2 million in the years ended December 31, 2025 and December 31, 2024, respectively. We expect to make significant investments to further develop and expand our business, particularly in marketing and advertising to expand our consumer base. As a public company, we have incurred and expect to continue to incur significant legal, accounting and other expenses. Despite these investments, we may not succeed in increasing our revenue on the timeline that we expect or in an amount sufficient to lower our net loss and ultimately become profitable. In addition, if we reduce variable costs to respond to losses, this may limit our ability to sign up new customers and grow our revenues. Accordingly, we may not achieve or maintain profitability and we may continue to incur significant losses in the future.

We have experienced significant customer growth since we commenced operations; however, we may not be able to maintain this growth and thus, our customer base could stop growing or even shrink over time.

Our ability to attract new customers and retain existing customers depends, in large part, on our ability to continue to be perceived as providing delightful and superior insurance-buying and claims- filing customer experiences, competitive pricing, and adequate insurance coverage. In order to maintain this perception, we may be required to incur significantly higher marketing and advertising expenses, costs related to improving our service, and lower margins in order to attract new customers and retain existing customers. If we fail to remain competitive on customer experience, pricing, and insurance coverage options, our ability to grow our business and generate revenue by attracting and retaining customers may be adversely affected.

There are many factors that could negatively affect our ability to grow our customer base, including if:

•we are unable to cost-effectively attract and convert customers through digital distribution channels (e.g., search, social media, app stores, and online advertising);

•underwriting constraints, competitive pressures (including competitors replicating our digital model), or failure to expand geographically or offer competitive new products limit growth;

•our digital platform is disrupted or performs poorly—whether due to our systems or third parties—resulting in degraded customer experience or impaired quoting, policy servicing, or claims payments; or

•customer trust in our brand, including perceptions of our chatbots and concerns regarding content, privacy, and security, deteriorates due to actual or alleged issues or negative publicity.

Our inability to overcome these challenges could impair our ability to attract new customers and retain existing customers, and could have a material adverse effect on our business, revenue, operating results and financial condition.

We must accurately and timely evaluate and pay claims that are made under our policies. Many factors affect our ability to pay claims accurately and timely, including the efficacy of our artificial intelligence claims processing, the training and experience of our claims adjusters, including our third-party claims administrators, and our ability to develop or select and implement appropriate procedures and systems to support our claims functions.

The speed by which our artificial intelligence technology allows us to process and pay claims is a differentiating factor for our business and an increase in the average time to process claims could undermine our reputation and position in the insurance marketplace. Any failure to pay claims accurately or timely could also lead to regulatory and administrative actions or material litigation, or result in damage to our reputation, any one of which could materially and adversely affect our business, financial condition, results of operations, and prospects.

If our claims adjusters or third party claims administrators are unable to effectively process our volume of non-automated claims, our ability to grow our business while maintaining high levels of customer satisfaction could be compromised, which in turn, could adversely affect our operating margins.

Our future growth and prospects depend on our ability to increase the premium per customer, as described in the section titled "Management's Discussion and Analysis of Financial Condition and Results of Operations." Our business model is premised on the expectation we can win customers early in their financial lives and retain them throughout their insurance life cycle.

•Failure to Retain Customers During Life Transitions: The purchase of a home or a new vehicle is a significant life event where customers are exposed to third-party service providers (such as mortgage brokers, real estate agents, or car dealers) who may influence their insurance choices in ways we cannot. If we cannot successfully transition our core renters base into higher-premium products like homeowners or car insurance, our ability to increase premium per customer will be materially impaired.

•Perception of Brand Quality vs. Incumbents: While we are a preferred brand among the next generation of buyers, as customers’ assets grow, they may perceive traditional, larger insurers as offering higher quality or more "stable" coverage due to their longevity and financial ratings. If this perception leads customers to switch to incumbents as their insurance expenditures increase, we will fail to capture the anticipated growth.

•Competitive Pricing Sensitivity: During major purchasing decisions, such as buying a home, the relative price difference between our products and those of our competitors may appear less significant to a consumer. If we are unable to maintain a competitive edge in both price and user experience during these transitions, our growth prospects will suffer.

•Acquisition of New High-Value Customers: Beyond retaining existing customers, our growth depends on successfully acquiring new homeowners and car owners directly or through partners. If we are unable to penetrate these higher-priced segments effectively, our revenue growth may stagnate.

If we fail to effectively manage these transitions or if our customers do not "graduate" to higher-premium products as expected, our results of operations and financial condition could be materially and adversely affected.

The markets in which we provide insurance are highly competitive. We compete against large traditional carriers who possess significant advantages in name recognition, financial ratings, capital resources, and the ability to offer "bundled" policies coverage at scale. Our future growth depends heavily on our ability to compete in all markets, including the homeowners and auto market where these traditional advantages are most pronounced. Furthermore, we face intense competition in specialized lines from Embrace and Trupanion in pet insurance, and from Progressive and GEICO in car insurance.

We also face increasing pressure from technology companies entering the insurance space, as well as traditional carriers adopting technology similar to ours to erode our current market advantages. These competitors may offer more aggressive pricing or superior resources, and our ability to counter them may be hindered if our new products face regulatory delays or fail to receive approval. If we are unable to compete effectively against both established insurance giants and tech-first entrants, our business and financial results will be materially and adversely affected.

We use artificial intelligence (“AI”) machine learning, and automated decision-making technologies, including proprietary AI and machine learning algorithms and models, (collectively “AI Technologies”) throughout our business, and are making significant investments in this area. For example, we utilize the data gathered from the insurance application process to determine whether or not to write a particular policy and, if so, how to price that particular policy. Similarly, we use proprietary AI Technologies to process many of our claims. The data that we gather through our interactions with our customers is evaluated and curated by proprietary AI Technologies.

We expect that increased investment will be required in the future to continuously improve our use of AI Technologies. As with many technological innovations, there are significant risks involved in developing, maintaining and deploying these technologies and there can be no assurance that the usage of or our investments in such technologies will always enhance our products or services or be beneficial to our business, including our efficiency or profitability.

In particular, if the models underlying our AI Technologies are incorrectly designed or implemented; trained or reliant on incomplete, inadequate, inaccurate, biased or otherwise poor quality data, or on data to which we do not have sufficient rights or in relation to which we and/or the providers of such data have not implemented sufficient legal compliance measures; used without sufficient oversight and governance to ensure their responsible use; and/or adversely impacted by unforeseen defects, technical challenges, cybersecurity threats or material performance issues, the performance of our business, as well as our reputation could suffer or we could incur liability resulting from the violation of laws or contracts to which we are a party or civil claims. In addition, we may incorrectly price insurance products for our customers or incorrectly pay or deny claims made by our customers, either of which could result in customer dissatisfaction with us, which could cause customers to cancel their insurance policies with us, prevent prospective customers from obtaining new insurance policies, or cause us to underprice policies or overpay claims.

We must have sufficient capital to comply with insurance regulatory requirements and maintain authority to conduct our business. The NAIC has developed a system to test the adequacy of statutory capital of U.S.-based insurers, known as risk-based capital that all states have adopted. This system establishes the minimum amount of capital necessary for an insurance company to support its overall business operations. It identifies insurers, including property-casualty insurers, that may be inadequately capitalized by looking at certain inherent risks of each insurer's assets and liabilities and its mix of net written premiums. Insurers falling below a calculated threshold may be subject to varying degrees of regulatory action, including supervision, rehabilitation or liquidation. Moreover, as a new entrant to the insurance industry, we may face additional capital requirements as compared to those of our larger and more established competitors. Failure to maintain adequate risk-based capital at the required levels could adversely affect the ability of our insurance subsidiaries to maintain regulatory authority to conduct its business. See "Regulation — Risk-Based Capital." Some parts of our business depend on our relationships and contractual arrangements with third parties.

If our third parties terminate business arrangements with us, or renew contracts on terms less favorable to us, we may fail to meet our business objectives and targets, and our cash flows, results of operations and financial condition could be adversely affected. For example, our life insurance product is offered through an arrangement with a life insurance provider. In these relationships, we rely on the third-party’s internal controls, to manage the product. Our monitoring efforts of the third party providers and other service providers may not be adequate, or our providers could exceed their authorities or otherwise breach obligations owed to us, which could result in operational disruption, reputational damage and regulatory intervention and otherwise have a material adverse effect on our results of operation and financial condition. Furthermore, these third parties are subject to many of the same risks that we face, including those related to cybersecurity and fraudulent claims. These parties also experience intense competition in the segments of the insurance industry in which they operate. They may be acquired or form alliances with our competitors thereby reducing or eliminating their business with us. If we are unsuccessful in our ability to maintain successful relationships with these third-party service providers and implement our arrangements with them for any of these reasons, our business may be adversely affected.

Our ability to increase revenue depends on our capacity to successfully launch new product offerings and expand into new geographic markets. Since 2020, we have diversified our portfolio by launching pet, life, and car insurance to complement our core renters and homeowners products, and in 2024, we expanded our offerings in the UK and France to include buildings insurance. However, entering these complex markets requires substantial investments of time and capital to gain a deep understanding of unique business challenges and customer needs; we may not be successful in these efforts. Furthermore, insurance regulations may limit our ability to introduce new products or restrict the states and countries in which we operate and regulatory approvals may take months to be obtained or may be rejected entirely.

Even if we successfully expand, managing this growth effectively presents significant operational risks. Our revenue grew from $429.8 million for the year ended December 31, 2023 to $526.5 million for the year ended December 31, 2024 and $737.9 million for the year ended December 31, 2025, placing substantial demands on our management, employees, and financial resources. As we add staff and enhance our internal controls, our organizational structure will become increasingly complex. This expansion requires significant capital expenditures and the allocation of management resources to ensure that our corporate culture of innovation and the quality of our customer experience are not undermined. If we cannot maintain the efficiency of our insurance-buying experience as we scale, our brand could be harmed, and our business, results of operations, and financial condition could be materially and adversely affected.

We use artificial intelligence, telematics, mobile technology, and our digital platforms to collect data that we evaluate in pricing and underwriting certain of our insurance policies, managing claims and customer support, and improving business processes. If federal, state or international regulators or courts were to determine that the type of data we collect, the process we use for collecting this data or how we use it unfairly discriminates against or otherwise violates the rights of some groups of people, laws and regulations could be interpreted or implemented to prohibit or restrict our ability to collect or use this data.

State legislatures and insurance regulators have also shown interest in the use of external data and artificial intelligence in insurance practices, including underwriting, marketing and claims practices. The NAIC adopted its Artificial Intelligence Principles in August 2020, a model bulletin titled “Use of Artificial Intelligence Systems by Insurers,” and a number of states have had legislative or regulatory initiatives relating to the use of external data and artificial intelligence in the insurance industry, including bulletins issued in 2022 by the California and Connecticut Departments of Insurance, and more recently in July 2024 by the New York State Department of Financial Services, advising insurers of their obligations related to unfair discrimination when using big data and artificial intelligence.

Due to Proposition 103 in California, our largest market for car insurance, we are currently limited in our ability to use telematics data beyond miles-driven to underwrite insurance, including data on how the car is driven. This could hinder our ability to accurately assess the risks that we underwrite in other states if they were to pass similar laws or regulations. In three other states where we currently operate, we do not use behavioral telematics data because it is either (a) permitted, but we opted out given uncertainty regarding the impact such data would have on pricing, or (b) it is voluntary (meaning the policyholder has to opt in). As we aim to be a fully national provider of insurance across 50 states and Washington, D.C. in the future, we will need to comply with the rules and regulations of each market. At this time, we do not know which of our target markets prohibit, permit with conditions, or fully permit the use of behavioral telematics to set premiums, and if permitted, if this will be of benefit to us in pricing. While we are currently in discussions with regulators to allow the use of telematics to a greater extent to underwrite and price insurance policies, we cannot predict the outcome of these discussions, and there can be no assurance that state regulators will revise regulations accordingly, if at all, nor that current permissive states will further restrict the use of such data. Although there is currently limited federal and state legislation outside of California restricting our ability to collect driving behavior data, private organizations are implementing principles and guidelines to protect driver privacy. Some state regulators have expressed interest in the use of external data sources, algorithms and/or predictive models in insurance underwriting or rating. Specifically, regulators have raised questions about the potential for unfair discrimination, disparate impact, and lack of transparency associated with the use of external consumer data. Regulators may also require us to disclose the external data we use, algorithms and/or predictive matters prior to approving our underwriting models and rates. Such disclosures could put our intellectual property at risk.

Additionally, the regulatory framework for AI Technologies is rapidly evolving as many federal state and foreign government bodies and agencies have enacted or are currently considering laws and regulations governing AI. Additionally, existing laws and regulations may be interpreted or enforced in ways that would affect our use of AI Technologies. As a result, implementation standards and enforcement practices are likely to remain uncertain for the foreseeable future, and we cannot predict the impact future laws, regulations, or standards, or the market perception of their requirements, may have on our business or how we will respond to these laws or regulations.

In the United States, the regulatory framework for AI Technologies faces significant uncertainty. At the federal level, Congress has yet to enact meaningful AI legislation. Instead, federal policy on AI has been shaped by a series of executive orders that have shifted priorities and requirements substantially depending on the administration in power. In October 2023, President Biden issued an Executive Order on the Safe, Secure, and Trustworthy Development and Use of Artificial Intelligence, which emphasized AI safety and security and addressed topics such as civil rights, privacy, consumer protection, and accountable federal use of AI. In January and July 2025, President Trump issued three executive orders on AI, one of which repealed President Biden’s 2023 Executive Order, shifting the focus towards removing regulatory barriers to the adoption of AI Technologies and accelerating AI deployment.

In the absence of federal AI legislation, states have filled the void by enacting laws regulating different aspects of AI Technologies. For example, California has enacted laws and regulations related to AI safety protocols, reporting and transparency, among other AI-related topics. In addition, Colorado’s Artificial Intelligence Act will require developers and deployers of “high-risk” AI systems to implement certain safeguards against algorithmic discrimination (among other requirements), and the Texas Responsible Artificial Intelligence Governance Act prohibits the development and deployment of AI systems for certain purposes while establishing a regulatory sandbox. Moreover, state AI laws such as Colorado’s Artificial Intelligence Act and various comprehensive state privacy laws, including the California Consumer Privacy Act (“CCPA”), regulate the use of automated decision making technology that results in legal or similarly significant effects on individuals, and provide rights to individuals with respect to that automated decision making. Many states have also enacted sector-specific AI laws, including related to the use of AI in connection with the provision of financial services.

Numerous other states have enacted, passed, or are considering AI-focused legislation, creating a patchwork of regulations and a complex compliance challenge. However, the durability of these laws and the potential of additional state-level legislative activity faces uncertainty following President Trump’s December 2025 Executive Order “Ensuring a National Policy Framework for Artificial Intelligence.” This Executive Order establishes a federal policy favoring a uniform national AI regulatory framework designed to promote innovation and U.S. global competitiveness. The order directs federal agencies to identify, challenge, and potentially pre-empt state and local AI laws that are viewed as inconsistent with or burdensome to this national approach. It remains to be seen how agencies will effectuate this directive, and how states will approach AI legislation moving forward. Any or all of the foregoing regulatory developments could affect our use of AI Technologies and our ability to provide, improve or commercialize our services, require changes to our operations and processes, and materially adversely affect our business, results of operations, and financial condition. Further, any failure or perceived failure by us to comply with existing or newly enacted laws, regulations and other requirements relating to AI Technologies could result in legal claims or proceedings (including class actions), regulatory investigations or enforcement actions.

There is also increasing focus on regulating the use of artificial intelligence and machine learning in Europe. The EU Artificial Intelligence Act (“EU AI Act”) establishes a comprehensive, risk-based governance framework for artificial intelligence in the EU market and the majority of the substantive requirements will apply from August 2, 2026. The EU AI Act applies to companies like ours that develop, use and/ or provide artificial intelligence in the EU. It imposes requirements around ensuring AI literacy for staff and transparency in the use of AI. For high risk use cases which include the use of AI in offering of health or life insurance, it imposes an extensive range of obligations including risk assessments, conformity assessments and monitoring, as well as human oversight. While we do not currently offer health or life insurance in the EU, these provisions will impose onerous requirements should we wish to expand our offering to do so, which may impact our ability to expand. Fines under the EU AI Act are up to 7% of global turnover for use of AI and up to 3% for other non-compliance. In addition, the revised EU Product Liability Directive to be implemented into EU Member State national law by December 2026 extends the EU’s existing strict product liability regime to artificial intelligence technologies and artificial intelligence-enabled products and facilitates civil claims in respect of harm caused by artificial intelligence. The EU AI Act and the EU Product Liability Directive will have a material impact on the way artificial intelligence is regulated in the EU, and together with developing guidance and/ or decisions in this area, is likely to affect our use of artificial intelligence and our ability to provide and to improve our services, require additional compliance measures and changes to our operations and processes, result in increased compliance costs and potential increases in civil claims against us, and could adversely affect our business, operations and financial condition. See also “We may face particular privacy, data security, and data protection risks as we continue to expand into Europe and the UK in connection with the GDPR, UK GDPR, and other data protection regulations”.

On November 19, 2025, the European Commission published the “Digital Omnibus Package,” which is a proposal to simplify the EU’s digital rule book on data, cybersecurity, and artificial intelligence. As the proposal is still under legislative review and subject to change, its final scope and impact on our operations remain uncertain. We continue to monitor these developments.

It is possible that further new laws and regulations will be adopted in the United States, Europe, and in other non-U.S. jurisdictions, or that existing laws and regulations, including competition and, antitrust, data privacy and consumer protection laws, may be interpreted or enforced in ways that would limit our ability to use AI Technologies for our business, or require us to change the way we use AI Technologies in a manner that negatively affects the performance of our business and the way in which we use AI Technologies. We may need to expend resources to adjust our products or services in certain jurisdictions if the laws, regulations, or decisions are not consistent across jurisdictions. Further, the cost to comply with such laws, regulations, or decisions and/or guidance interpreting existing laws, could be significant and would increase our operating expenses (such as by imposing additional reporting obligations regarding our use of AI Technologies). Such an increase in operating expenses, as well as any actual or perceived failure to comply with such laws and regulations, could adversely affect our business, financial condition and results of operations. In addition, if we fail or are perceived to fail to comply with these laws and regulations, we may face lawsuits (including class actions), investigations, enforcement actions, negative reputational impacts, and other penalties that materially impact our business.

In general, the premiums for our insurance policies are established at the time a policy is issued and, therefore, before all of our underlying costs are known. The accuracy of our pricing is subject to our ability to adequately assess risks, estimate losses and comply with state insurance regulations. Like other insurance companies, we rely on estimates and assumptions in setting our premium rates. We also utilize the data that we gather through our interactions with our customers, as evaluated and curated by our proprietary artificial intelligence algorithms.

Establishing adequate premium rates is necessary, together with investment income, if any, to generate sufficient revenue to offset losses, loss adjustment expenses and other costs. Changes in U.S. trade policy, including tariffs on imported goods, may increase claims costs that are not immediately reflected in our premium rates due to regulatory approval timing. If we do not accurately assess the risks that we underwrite, we may not charge adequate premiums to cover our losses and expenses, which would adversely affect our results of operations and our profitability. Moreover, if we determine that our prices are too low, insurance regulations may preclude us from being able to cancel insurance contracts, non-renew customers, or raise prices. Alternatively, we could set our premiums too high, which could reduce our competitiveness and lead to lower revenues, which could have a material adverse effect on our business, results of operations and financial condition.

Pricing involves the acquisition and analysis of historical loss data and the projection of future trends, loss costs and expenses, and inflation trends, among other factors, for each of our products in multiple risk tiers and many different markets. In order to accurately price our policies, we must:

•collect and properly analyze a substantial volume of data from our customers;

•develop, test and apply appropriate actuarial projections and rating formulas;

•review and evaluate competitive product offerings and pricing dynamics;

•closely monitor and timely recognize changes in trends; and

•project both frequency and severity of our customers' losses with reasonable accuracy.

There are no assurances that we will have success in implementing our pricing methodology accurately in accordance with our assumptions. Our ability to accurately price our policies is subject to a number of risks and uncertainties, including:

•insufficient or unreliable data;

•incorrect or incomplete analysis of available data;

•uncertainties generally inherent in estimates and assumptions;

•our failure to implement appropriate actuarial projections and rating formulas or other pricing methodologies;

•incorrect or incomplete analysis of the competitive environment;

•regulatory constraints on rate increases; and

•our failure to accurately estimate investment yields and the duration of our liability for loss and loss adjustment expense, as well as unanticipated court decisions, legislation or regulatory action.

To address the potential inadequacy of our current business model, we may be compelled to increase the amount allocated to cover policy claims, increase premium rates or adopt tighter underwriting standards, any of which may result in a decline in new business and renewals and, as a result, could have a material adverse effect on our business, results of operations and financial condition.

Our strategy for Lemonade Car involves a long-term orientation toward a future where insurance pricing reflects whether a human or AI is driving. We recently launched autonomous pricing for self-driving technologies which uses direct vehicle telemetry to distinguish between autonomous and human-driven miles, pricing the former at 50% of the human-driven rate. This model is subject to several risks:

Reliance on Safety Outcomes: Our current and future pricing for autonomous miles depends on data continuing to show improving safety outcomes for self-driving technologies If these outcomes fail to improve as expected or if data indicates increased risk, we may be forced to raise rates, which could reduce our competitiveness and growth.

Technological and Regulatory Shifts: While we believe we are positioned to capitalize on the shift toward autonomous driving, this field is evolving rapidly. Any significant changes in autonomous driving capabilities, real-world utilization, or regulations governing the use of vehicle telemetry for pricing could undermine our infrastructure and convictions regarding autonomy-aware pricing.

Data Precision and Interconnectivity: Our product relies on precisely mapping direct vehicle telemetry to separate autonomous and human miles. Any technical failure to accurately distinguish these miles or interruptions in data flow from vehicle manufacturers could lead to inaccurate pricing and materially affect our results of operations.

If we are unable to accurately price the risks associated with evolving driving technologies, if we are unable to utilize the information appropriately, or if incumbents move faster to adapt to these shifts, our business and financial condition could be adversely affected.

To the extent that our capital is insufficient at any point in time to meet future operating requirements (including regulatory capital requirements) or to cover losses, we may need to raise additional funds through financings or curtail our projected growth. Many factors will affect our capital needs as well as their amount and timing, including our growth and profitability, the availability of reinsurance, as well as market disruptions and other developments.

Historically, we have funded our operations, marketing expenditures and capital expenditures primarily through equity issuances, cash from operations and our Customer Investment Agreement with GC Customer Value Arranger LLC. We evaluate financing opportunities from time to time, and our ability to obtain financing will depend, among other things, on our development efforts, business plans and operating performance, and the condition of the capital markets at the time we seek financing. In addition, the NYDFS, Delaware Department of Insurance ("DE Dept."), California Department of Insurance ("CDI"), and other regulatory bodies may not permit additional equity issuances or other forms of financing that we may wish to pursue. We cannot be certain that additional financing will be available to us on favorable terms, or at all.

If we raise additional funds through the issuance of equity, equity-linked or debt securities, those securities may have rights, preferences or privileges senior to those of our common stock, and our existing stockholders may experience dilution. Furthermore, any debt financing secured by us in the future could require a substantial portion of our operating cash flow to be allocated to payment of interest and principal, which may reduce available funds for other business activities, and could involve restrictive covenants relating to our capital-raising activities and other financial and operational matters, which may make it more difficult for us to obtain additional capital and to pursue business opportunities.

If we are unable to obtain adequate financing or financing on terms satisfactory to us, when required, our ability to continue to support our business growth, maintain minimum amounts of risk-based capital and to respond to business challenges could be significantly limited, and our business, results of operations and financial condition could be adversely affected.

We offer our products through our website and online app using Amazon Web Services ("AWS") data centers, a provider of cloud infrastructure services. We do not have control over the operations of the facilities of AWS that we use. AWS’s facilities are vulnerable to damage or interruption from human error, intentional bad acts, earthquakes, floods, fires, severe storms, war, terrorist attacks, power losses, hardware failures, systems failures, telecommunications failures, and similar events, many of which are beyond our control, any of which could disrupt our services, prevent customers from accessing our products, destroy customer data, or prevent us from being able to continuously back up and record data. If our data centers or related systems fail to operate properly or become disabled even for a brief period of time, we could suffer financial loss, a disruption of our business, liability to customers or damage to our reputation. We may not be able to easily switch our AWS operations to another cloud or other data center provider if there are disruptions or interference with our use of AWS, and other cloud and data center providers are subject to the same risks. Moreover, negative publicity arising from these types of disruptions could damage our reputation and may adversely impact use of our website and online app. We may not carry sufficient business interruption insurance, it may not be sufficient to compensate us for the potentially significant losses, including the potential harm to the future growth of our business that may result from interruptions in our services or products.

AWS enables us to order and reserve server capacity in varying amounts and sizes distributed across multiple regions and provides us with computing and storage capacity pursuant to an agreement that continues until terminated by either party. Termination of the AWS agreement may harm our ability to access data centers we need to host our website and online app or to do so on terms as favorable as those we have with AWS.

As we continue to expand the number of customers to whom we provide our products and services, we may not be able to scale our technology to accommodate the increased capacity requirements, which may result in interruptions or delays in service. In addition, the failure of AWS data centers or third-party internet service providers to meet our capacity requirements could result in interruptions or delays in access to our website or online app or impede our ability to scale our operations. In the event that our AWS service agreements are terminated, or there is a lapse of service, interruption of internet service provider connectivity or damage to such facilities, we could experience interruptions in access to our website or online app as well as delays and additional expense in arranging new facilities and services, which could harm our business, results of operations, and financial condition.

We rely on computer systems, hardware, software, technology infrastructure and online sites and networks for both internal and external operations that are critical to our business (collectively, “IT Systems”). We own and manage some of these IT Systems but also rely on third parties for a range of IT Systems and related products and services. We and certain of our third-party providers collect, maintain and process data about customers, employees, business partners and others, including information about individuals, as well as proprietary information belonging to our business such as trade secrets (collectively, “Confidential Information”). Our continued success is dependent on our IT Systems to meet the changing needs of our customers and users. We rely on our technology and engineering staff and vendors to successfully implement changes to and maintain our IT Systems in an efficient and secure manner. We face numerous and evolving cybersecurity risks that threaten the confidentiality, integrity and availability of our IT Systems and Confidential Information, including from diverse threat actors, such as state-sponsored organizations, opportunistic hackers and hacktivists, as well as through diverse attack vectors, such as social engineering/phishing, malware (including ransomware), malfeasance by insiders, human or technological error, and as a result of malicious code embedded in open-source software, or misconfigurations, bugs or other vulnerabilities in commercial software that is integrated into our (or our suppliers’ or service providers’) IT Systems, products or services.

Cyberattacks are expected to accelerate on a global basis in frequency and magnitude as threat actors are becoming increasingly sophisticated in using techniques and tools - including AI - that circumvent security controls, evade detection and remove forensic evidence. As a result, we may be unable to detect, investigate, remediate or recover from future attacks or incidents, or to avoid a material adverse impact to our IT Systems, Confidential Information or business. There can also be no assurance that our cybersecurity risk management program and processes, including our policies, controls or procedures, will be fully implemented, complied with or effective in protecting our IT Systems and Confidential Information. Furthermore, given the nature of complex systems, software and services like ours, and the scanning tools that we deploy across our networks and products, we regularly identify and track security vulnerabilities. We are unable to comprehensively apply patches or confirm that measures are in place to mitigate all such vulnerabilities, or that patches will be applied before vulnerabilities are exploited by a threat actor.

We and certain of our third-party providers regularly experience cyberattacks and other incidents, and we expect such attacks and incidents to continue in varying degrees. If we experience compromises to our security that result in technology performance, integrity, or availability problems, the complete shutdown of our website or our online app or the loss or unauthorized disclosure, access, acquisition, alteration or use of confidential information, customers may lose trust and confidence in us, and customers may decrease the use of our website or our online app, or stop using our website or our online app entirely. Further, outside parties may attempt to fraudulently induce employees or customers to disclose sensitive information in order to gain access to our Confidential Information. Because the techniques used to obtain unauthorized access, disable or degrade service, or sabotage systems change frequently, often they are not recognized until launched against a target, and may originate from less regulated and remote areas around the world, we may be unable to proactively address these techniques or to implement adequate preventative measures. Even if we take steps that we believe are adequate to protect us from cyber threats, hacking against our competitors or other companies could create the perception among our customers or potential customers that our digital platform is not safe to use. There can also be no assurance that our cybersecurity risk management program and processes, including our policies, controls or procedures, will be fully implemented, complied with or effective in protecting our IT Systems and Confidential Information.

Any adverse impact to the availability, integrity or confidentiality of our IT Systems or Confidential Information can result in legal claims or proceedings (such as class actions), regulatory investigations and enforcement actions, fines and penalties, negative reputational impacts that cause us to lose existing or future customers, and/or significant incident response, system restoration or remediation and future compliance costs. A significant impact on the performance, reliability, security, and availability of our systems, software, or services may harm our reputation, impair our ability to operate, retain existing customers or attract new customers, and expose us to legal claims and government action. Any or all of the foregoing could materially adversely affect our business, results of operations, and financial condition. Finally, we cannot guarantee that any costs and liabilities incurred in relation to an attack or incident will be covered by our existing insurance policies or that applicable insurance will be available to us in the future on economically reasonable terms or at all.

We provide insurance through our U.S. subsidiaries, LIC and MIC. Since LIC is a New York State-domiciled insurance company, LIC’s primary insurance regulator responsible for supervision and examination is the NYDFS. Since MIC is domiciled in Delaware and is commercially domiciled in California, MIC’s primary insurance regulators responsible for supervision and examination are the Delaware Department of Insurance and the California Department of Insurance. LIC and MIC are subject to a financial examination by their primary insurance regulators generally every three to five years, under which they will evaluate the financial condition and identify current and prospective risks of each company by obtaining information about each company including corporate governance, identifying and assessing inherent risks within each company and evaluating system controls and procedures used to mitigate those risks. In 2024, the NYDFS completed a group financial exam of LIC and MIC covering the years 2019 through 2022 for LIC, and 2021 and 2022 for MIC. All required remediation pursuant to the group financial exam was completed in 2024, however, we cannot predict with precision the likelihood, nature, or extent of any necessary remedial actions in any future examinations.

In addition, insurance regulators of other states in which we are licensed to operate periodically conduct market conduct examinations or other targeted investigations. We are presently subject to, and in the future will continue to be subject to, such examination and investigations. Any regulatory or enforcement action or any regulatory order imposing remedial, injunctive, or other corrective action against us resulting from these examinations or investigations could have a material adverse effect on our business, reputation, financial condition or results of operations. The results of each examination can give rise to fines and monetary penalties as well as regulatory orders requiring remedial, injunctive, or other corrective action.

Reinsurance is a contract by which an insurer, which may be referred to as the ceding insurer, agrees with a second insurer, called a reinsurer, that the reinsurer will cover a portion of the losses incurred by the ceding insurer in the event a claim is made under a policy issued by the ceding insurer, in exchange for a premium. Our insurance subsidiaries, LIC, MIC and NV, obtain reinsurance to help manage their exposure to property and casualty insurance risks. Although our reinsurance counterparties are liable to us according to the terms of the reinsurance policies, we remain primarily liable to our policyholders as the direct insurers on all risks reinsured. As a result, reinsurance does not eliminate the obligation of our insurance subsidiaries to pay all claims, and we are subject to the risk that one or more of our reinsurers will be unable or unwilling to honor its obligations, that the reinsurers will not pay in a timely fashion, or that our losses are so large that they exceed the limits inherent in our reinsurance contracts, limiting recovery. Reinsurers may become financially unsound by the time that they are called upon to pay amounts due, which may not occur for many years, in which case we may have no legal ability to recover what is due to us under our agreement with such reinsurer. Any disputes with reinsurers regarding coverage under reinsurance contracts could be time consuming, costly, and uncertain of success.

Under the Proportional Reinsurance Contracts, we transfer, or “cede,” a specified percentage of our premiums to our reinsurers. In exchange, these reinsurers pay us a “ceding commission” on all premiums ceded to the Reinsurers, in addition to funding the corresponding claims, subject to certain limitations. We have also opted to manage the remaining portion of our business with alternative forms of reinsurance through the Non-Proportional Reinsurance Contracts. Our business is exposed to the risk of severe weather conditions and other catastrophes which are inherently unpredictable. If we are unable to renegotiate, at the same or more favorable terms, the Proportional Reinsurance Contracts or the Non-Proportional Reinsurance Contracts when each expires, such changes could have an adverse impact on our business model.

We may change the structure of our reinsurance arrangement in the future, which may impact our overall risk profile and financial and capital condition. We may be unable to negotiate a new reinsurance contract to provide continuous coverage or negotiate reinsurance on the same terms and rates as are currently available, as such availability depends in part on factors outside of our control. A new contract may not provide sufficient reinsurance protection. Market forces and external factors, such as significant losses from hurricanes or terrorist attacks or an increase in capital requirements, impact the availability and cost of the reinsurance we purchase. If we were unable to maintain our current level of reinsurance, extend our reinsurance contracts or purchase new reinsurance protection in amounts that we consider sufficient at acceptable prices, we would have to either accept an increase in our exposure, reduce our insurance writings or develop or seek other alternatives.

The unavailability of acceptable reinsurance cover would have an adverse impact on our business model, which depends on reinsurance companies to absorb any unfavorable variance from the level of losses anticipated at underwriting. If we are unable to obtain adequate reinsurance at reasonable rates, we would have to increase our risk exposure or reduce the level of our underwriting commitments, each of which could have a material adverse effect upon our business volume and profitability. Alternatively, we could elect to pay higher than reasonable rates for reinsurance coverage, which could have a material adverse effect upon our profitability until policy premium rates could be raised, in most cases subject to approval by state regulators, to offset this additional cost. Moreover, if adequate reinsurance cannot be obtained or maintained at reasonable rates, we may be unable to make contributions to the nonprofit causes selected by our customers as part of our Giveback, which could erode customer trust, damage our brand, and have a material adverse effect on our financial condition and results of operations.

The GDPR applies to the processing of personal data by our business in the context of our establishments in the European Union and/or the UK. In addition, all portions of our business established outside the European Union and the UK may be required to comply with the requirements of the GDPR with respect to the offering of products or services to individuals in the European Union or UK. The GDPR could also apply to our establishments of business outside the European Union and the UK if we were to monitor the activities of individuals. The GDPR increases the maximum level of fines for the most serious compliance failures to the greater of four percent of annual worldwide turnover or €20,000,000 / GBP17,500,000, respectively.

We may also be subject to the local privacy and data protection laws of the E.U. Member States in which we offer products or services, which can carry penalties and potential criminal sanctions.

The regulatory requirements and restrictions set out in the GDPR include, among others, the following:

•The GDPR imposes a number of principles with respect to the processing of personal data, including requirements to process personal data lawfully, fairly, and in a transparent manner, to process personal data only to the extent necessary for the purposes required, maintain the accuracy of personal data, limit the retention of personal data for no longer than is necessary, and maintain appropriate technical and organizational security measures against unauthorized processing or accidental loss, destruction, or damage. We are implementing external and internal policies and procedures, technical measures and internal training designed to adhere to those principles;

•In relation to the transparency principle, the GDPR requires us to provide individuals in the European Union and the UK whose personal data we process ("data subjects") with certain information regarding the processing of their personal data by us, and we have an EU and UK privacy policy, which can be found at https://www.lemonade.com/de/en/privacy-policy (with respect to Germany), https://www.lemonade.com/nl/en/privacy-policy (with respect to the Netherlands) and http://www.lemonade.com/fr/en/privacy-policy (with respect to France); and https://www.lemonade.com/uk/privacy-policy (with respect to UK);

•The GDPR requires us to maintain internal records of our processing activities and to make those records available to regulators on demand;

•The GDPR requires us to include mandatory terms in our agreements with third parties that process personal data subject to the GDPR on our behalf ("Processors"). To comply with this requirement, we enter into Data Processing Addenda (“DPA’s”) with Processors to contractually ensure they process data only according to our instructions. If a third party violates the terms of the DPA, it could lead to regulatory penalties or an an adverse impact on our business;

•The GDPR grants data subjects various rights, including the right to access, copy, or object to the processing of their personal data. as well as the right to erasure {“right to be forgotten”). We have implemented internal policies and procedures, including specific response timelines and data retention protocols, designed to systematically address and fulfill these requests in compliance with regulatory requirements;

•The GDPR prohibits automated decision making, i.e. a decision evaluating a data subject's personal aspects based solely on automated processing that produces legal effects or other significant effects for that data subject, except where such decision making is necessary for entering into or performing a contract or is based on the data subject's explicit consent. There is not yet any clear precedent as to whether use of artificial intelligence to make insurance offers to individuals will be considered necessary even though it is integral to our business model. If our automated decision making processes cannot meet this necessity threshold, we cannot use these processes with E.U. data subjects unless we obtain their explicit consent. Notably for the UK, in 2025, the Data Use and Access Act (“DUAA”) came into force, which relaxed the restrictions around automated decision-making to only apply when the decision involves special category data such as health, race, region, or biometric data. However, this change under UK law does not alter the fact that automated decision-making of non-special category data must still be communicated to the data subject. Relying on consent to conduct this type of processing holds its own risks because consent must be considered freely given (commentators argue that seeking consent by tying it to a service may be problematic) and consent can be withdrawn by a data subject at any time. We are continually monitoring for updates to guidance in this area, however, if subsequent guidance and/or decisions limit our ability to use our artificial intelligence models, that may decrease our operational efficiency and result in an increase to the costs of operating our business. Automated decision making also attracts a higher regulatory burden under the GDPR, which requires the existence of such automated decision making be disclosed to the data subject including a meaningful explanation of the logic used in such decision making, and safeguards must be implemented to safeguard individual rights, including the right to obtain human intervention and to contest any decision. Further obligations in terms of transparency have and are likely to continue to be imposed under new laws regulating AI, including the EU AI Act with the majority of its substantive requirements applying from August 2, 2026. See “We rely on artificial intelligence, telematics, mobile technology, and our digital platforms to collect data that we evaluate in pricing and underwriting our insurance policies, managing claims and customer support, and improving business processes, and any legal or regulatory requirements that prohibit or restrict our ability to collect or use this data could materially and adversely affect our business, financial condition, results of operations and prospects”; and

•The GDPR also places limits on the profiling of individuals, i.e. processing of personal data to evaluate certain personal aspects, like analyzing or predicting aspects of a person's economic situation, health, personal preferences, location, etc. There is increasing enforcement related to the lawfulness, fairness and transparency of this processing, and there is still uncertainty about the relevant lawful basis for this activity (i.e., consent or legitimate interests) and, in the case of legitimate interests, it is unclear what kind of opt-out or objection mechanism would be required to achieve GDPR compliance. We are continually monitoring for updates to guidance in this area, however, if subsequent guidance and/or decisions limit our ability to engage in profiling, that may decrease our operational efficiency and result in an increase to the costs of operating our business.

The DUAA brought about other key changes as well. For instance, there is a new lawful basis for data processing in the form of “recognized legitimate interests.” These recognized legitimate interests are specific types of processing activities that are automatically considered lawful, for example, fraud detection and prevention, information security, crime prevention, and public health and safety. Contrary to regular legitimate interests, recognized legitimate interests do not require the controller to conduct and document a legitimate interest assessment to ensure that processing activities fulfil the contemplated purpose, are necessary, and override the interests and fundamental rights and freedoms of a data subject. A considerable number of Lemonade’s processing activities serve the purpose of fraud detection/prevention. In the future, when Lemonade seeks a lawful basis for its UK processing activities that serve a recognized legitimate interest, it will not need to conduct a legitimate interest assessment.

We are also subject to European Union rules with respect to cross-border transfers of personal data out of the European Economic Area (“EEA”) and the UK.

We currently rely on the EU standard contractual clauses and the UK Addendum to the EU standard contractual clauses and the UK International Data Transfer Agreement as relevant to transfer personal data outside the EEA and the UK with respect to both intragroup and third party transfers. We expect the existing legal complexity and uncertainty regarding international personal data transfers to continue and international transfers to the United States and to other jurisdictions more generally to continue to be subject to enhanced scrutiny by regulators. As the regulatory guidance and enforcement landscape in relation to data transfers continue to develop, we could suffer additional costs, complaints and/or regulatory investigations or fines; we may have to stop using certain tools and vendors and make other operational changes; we may have to implement revised standard contractual clauses for existing intragroup, customer and vendor arrangements within required time frames; and/or it could otherwise affect the manner in which we provide our services, and could adversely affect our business, operations and financial condition.

In respect of the GDPR’s obligations, we rely on positions and interpretations of the law that have yet to be fully tested before the relevant courts and regulators. If a regulator or court of competent jurisdiction determined that one or more of our compliance efforts does not satisfy the applicable requirements of the GDPR, or if any party brought a claim in this regard, there could be potential governmental or regulatory investigations, enforcement actions, regulatory fines, compliance orders, litigation or public statements against us by consumer advocacy groups or others, and that could cause customers to lose trust in us and damage our reputation. Likewise, a change in guidance could be costly and have an adverse effect on our business.

We are also subject to evolving EU and UK privacy laws on cookies, tracking technologies and e-marketing. Recent European court and regulator decisions are driving increased attention to cookies and tracking technologies. If the trend of increasing enforcement by regulators of the strict approach to opt-in consent for all but essential use cases, as seen in recent guidance and decisions continues this may increase the cost of operating our business and lead to a decline in revenues and impair our ability to collect user information. However, note that pursuant to the DUAA, consent will no longer be required for the placement of certain types of storage and access technologies (e.g., cookies), including analytics, site optimization, and website functionality. In addition, legal uncertainties about the legality of cookies and other tracking technologies may lead to regulatory scrutiny and increase potential civil liability under data protection or consumer protection laws. Any such changes may force us to incur substantial costs or require us to change our business practices which could compromise our ability to pursue our growth strategy effectively and may adversely affect our ability to acquire customers or otherwise harm our business, financial condition and operating results. In light of the complex and evolving nature of EU, EU Member State and UK privacy laws on cookies and tracking technologies be successful in our efforts to comply with such laws; violations of such laws could result in regulatory investigations, fines, orders to cease/ change our use of such technologies, as well as civil claims including class actions, and reputational damage.

In August 2025, Amendment 13 to the Israeli Protection of Privacy Law, 5741-1981, came into force, significantly reforming Israeli privacy laws. The Amendment expanded the enforcement powers of the Israeli Privacy Protection Authority, including its authority to impose substantial financial fines of up to 5% of an organization’s annual turnover. It also introduced additional requirements for the processing of personal data, broadened certain existing obligations, and expanded the authority of the courts to award statutory damages without proof of damage for violations. The Amendment therefore could affect our operations in Israel regarding the processing of personal data.

We also continue to monitor developments in private litigation in the U.S. arising from the use of online tracking technologies. Over the past several years, plaintiffs’ firms have filed numerous class action lawsuits alleging that website operators deploy third-party analytics or targeted advertising tools without first obtaining users’ affirmative consent. These suits generally assert that, by allowing such third-party trackers to collect data, the website operator has facilitated the unlawful interception of user communications in violation of the California Invasion of Privacy Act (“CIPA”), the federal Electronic Communications Privacy Act (“ECPA”), and similar state statutes.

More recently, plaintiffs have advanced related theories claiming that the use of these tracking technologies constitutes the operation of an unlawful pen register or trap-and-trace process under these same laws. Although these statutes are criminal in nature, they provide private rights of action that may include statutory damages on a per-violation basis (for example, up to $5,000 per alleged violation under CIPA). These claims remain active and continue to evolve, and adverse outcomes could result in significant monetary exposure or injunctive obligations.

Any significant change to applicable laws, regulations, interpretations of laws or regulations, or market practices, regarding the use of personal data, or regarding the manner in which we seek to comply with applicable laws and regulations, could require us to make modifications to our products, services, policies, procedures, notices, and business practices, including potentially material changes. Such changes could potentially have an adverse impact on our business.

From time to time, third parties may misappropriate our data through website scraping, bots or other means and aggregate this data on their websites with data from other companies. In addition, copycat websites or online apps may misappropriate data and attempt to imitate our brand or the functionality of our website or our online app. If we become aware of such websites or online apps, we intend to employ technological or legal measures in an attempt to halt their operations. However, we may be unable to detect all such websites or online apps in a timely manner and, even if we could, technological and legal measures may be insufficient to halt their operations. In some cases, particularly in the case of websites or online apps operating outside of the United States, our available remedies may not be adequate to protect us against the effect of the operation of such websites or online apps. Regardless of whether we can successfully enforce our rights against the operators of these websites or online apps, any measures that we may take could require us to expend significant financial or other resources, which could harm our business, results of operations or financial condition. In addition, to the extent that such activity creates confusion among consumers or advertisers, our brand and business could be harmed.

Customers could purchase policies that prove to be inadequate or inappropriate, and if such customers were to bring a claim or claims alleging that we failed in our responsibilities to provide them with the type or amount of coverage that they sought to purchase, Lemonade Insurance Agency, LLC or Metromile Insurance Services LLC could be found liable, resulting in an adverse effect on our business, results of operations and financial condition. While we maintain agents errors and omissions insurance coverage to protect us against such liability, such coverage may be insufficient or inadequate.

Because our products are highly-advanced and require rigorous testing and regulatory approvals, development cycles can be complex. Moreover, development projects can be technically challenging and expensive, and may be delayed or defeated by the inability to obtain licensing or other regulatory approvals. The nature of these development cycles may cause us to experience delays between the time we incur expenses associated with research and development and the time we generate revenues, if any, from such expenses. If we expend a significant amount of resources on research and development and our efforts do not lead to the successful introduction or improvement of products that are competitive in the marketplace, this could materially and adversely affect our business and results of operations. Additionally, anticipated customer demand for a product we are developing could decrease after the development cycle has commenced. Such decreased customer demand may cause us to fall short of our sales targets, and we may nonetheless be unable to avoid substantial costs associated with the product's development. If we are unable to complete product development cycles successfully and in a timely fashion and generate revenues from such future products, the growth of our business may be harmed.

Litigation and other proceedings may include, but are not limited to, complaints from or litigation by customers or reinsurers, related to alleged breaches of contract or otherwise. As our market share increases, competitors may pursue litigation to require us to change our business practices or offerings and limit our ability to compete effectively. As is typical in the insurance industry, we continually face risks associated with litigation of various types arising in the normal course of our business operations, including disputes relating to insurance claims under our policies as well as other general commercial and corporate litigation. Although we are not currently involved in any material litigation with our customers, us and other members of the insurance industry are the target of class action lawsuits and other types of litigation, some of which involve claims for substantial or indeterminate amounts, and the outcomes of which are unpredictable. This litigation is based on a variety of issues, including sale of insurance and claim settlement practices. In addition, because we employ artificial intelligence to collect data points, customers or consumer groups have brought and could bring individual or class action claims alleging that our methods of collecting or using data and pricing risk are impermissibly discriminatory or otherwise improper. We cannot predict with any certainty whether we will be involved in such material litigation in the future or what impact such material litigation would have on our business. If we were to be involved in litigation and it was determined adversely, it could require us to pay significant damage amounts or to change aspects of our operations, either of which could have a material adverse effect on our financial results. Even claims without merit can be time-consuming and costly to defend and may divert management's attention and resources away from our business and adversely affect our business, results of operations and financial condition. Additionally, routine lawsuits over claims that are not individually material could in the future become material if aggregated with a substantial number of similar lawsuits. In addition to increasing costs, a significant volume of customer complaints or litigation could adversely affect our brand and reputation, regardless of whether such allegations are valid or whether we are liable. We cannot predict with certainty the costs of defense, the costs of prosecution, insurance coverage or the ultimate outcome of litigation or other proceedings filed by or against us, including remedies or damage awards, and adverse results in such litigation, and other proceedings may harm our business and financial condition. See "Legal Proceedings." The "Lemonade" brand may not become as widely known as incumbents' brands or the brand may become tarnished.

Many of our competitors have brands that are well recognized. As a relatively new entrant into the insurance market, we spend considerable money and other resources to create brand awareness and build our reputation. We may not be able to build brand awareness, and our efforts at building, maintaining and enhancing our reputation could fail. Complaints or negative publicity about our business practices, our marketing and advertising campaigns, our compliance with applicable laws and regulations, the integrity of the data that we provide to consumers or business partners, data privacy and security issues, and other aspects of our business, whether valid or not, could diminish confidence in our brand, which could adversely affect our reputation and business. As we expand our product offerings and enter new markets, we need to establish our reputation with new customers, and to the extent we are not successful in creating positive impressions, our business in current and new markets could be adversely affected. We may not be able to maintain or enhance our reputation, and failure to do so could materially adversely affect our business, results of operations and financial condition. If we are unable to maintain or enhance consumer awareness of our brand cost-effectively, our business, results of operations and financial condition could be materially adversely affected.

Our success depends in significant part on our ability to expand into additional markets in the United States and abroad. As of December 31, 2025, we were licensed to sell renters, homeowners, pet and/or car insurance policies in 50 states of the United States and Washington D.C. We operate in 41 of those states and Washington D.C. covering approximately 95% of the U.S. population. We have targeted coverage across all 50 states, but we cannot guarantee that we will be able to provide nationwide coverage in the near term or at all. Moreover, one or more states could revoke our license to operate, or implement additional regulatory hurdles that could inhibit our ability to obtain or maintain our license in such states.

In addition to growing our domestic business, we continue to expand our presence internationally, particularly in Europe. We hold a pan-European license, which enables us to sell in 30 countries across Europe. We also hold branch authorization permits in the UK which allows us to operate on a permanent basis in the UK market. We currently operate in Germany, the Netherlands, France and the UK and will continue to expand our product offerings in other countries. Operating outside of the United States may require significant management attention to oversee operations over a broad geographic area with varying cultural norms and customs, in addition to placing strain on our finance, analytics, compliance, legal, engineering, and operations teams. Moreover, international operations are subject to risks and uncertainties inherent in operating in these regions, including political unrest, such as the current situation with Ukraine and Russia. We may incur significant operating expenses and may not be successful in our international expansion for a variety of reasons, including:

•obtaining any required government approvals, licenses or other authorizations;

•complying with varying laws and regulatory standards, including with respect to the insurance business and insurance distribution, capital and outsourcing requirements, data privacy, tax and local regulatory restrictions;

•recruiting and retaining talented and capable employees in foreign countries;

•competition from local incumbents that better understand the local market, may market and operate more effectively and may enjoy greater local affinity or awareness;

•differing demand dynamics, which may make our product offerings less successful;

•currency exchange restrictions or costs and exchange rate fluctuations;

•operating in jurisdictions that do not protect intellectual property rights to the same extent as the United States; and

•limitations on the repatriation and investment of funds as well as foreign currency exchange restrictions.

Our limited experience in operating our business internationally increases the risk that any potential future expansion efforts that we may undertake may not be successful. If we invest substantial time and resources to expand our operations internationally and are unable to manage these risks effectively, our business, results of operations and financial condition could be adversely affected.

In addition, international expansion may increase our risks in complying with various laws and standards, including with respect to anti-corruption, anti-bribery, anti-money laundering, export controls, and trade and economic sanctions.

Expansion into new markets here and abroad will require additional investments by us in both regulatory approvals and marketing. These incremental costs may include hiring additional personnel, as well as engaging third-party service providers and other research and development costs. If we fail to grow our geographic footprint or geographic growth occurs at a slower rate than expected, our business, results of operations and financial condition could be materially and adversely affected.

On February 3, 2025, we entered into the Amended and Restated Customer Investment Agreement with GC (both as defined in Note 13 of the consolidated financial statements and below), extending our arrangement with GC to provide financing our sales and marketing growth efforts. Under the Amended and Restated Customer Investment Agreement, GC will provide up to an additional $200 million of financing from January 1, 2026 to December 31, 2026.

As of December 31, 2025, we had $158.1 million of outstanding borrowings under the Amended and Restated Agreement. We incurred interest expense of $17.3 million for the year ended December 31, 2025. Under the Amended and Restated Customer Investment Agreement, GC finances up to 80% of our growth spend (the “Investment Amount”), after which we are obligated to pay GC a percentage of premium collections from customers until the Investment Amount, plus 16% rate of return, is repaid. The Amended and Restated Customer Investment Agreement is intended to deliver cash flow benefits to support our sales and marketing growth efforts. There can be no guarantee that this financing structure will function as intended, and its failure to do so could materially and adversely impact our financial condition and results of operations.

Our future success depends on our ability to continue to develop and implement our proprietary artificial intelligence algorithms, and to maintain the confidentiality of this technology. Changes to existing regulations, their interpretation or implementation, or new regulations could impede our use of this technology, or require that we disclose our proprietary technology to our competitors, which could impair our competitive position and result in a material adverse effect on our business, results of operations, and financial condition.

U.S. state and federal, and foreign lawmakers, and insurance regulators are focusing upon the use of AI broadly, including concerns about transparency, deception, and fairness in particular. Changes in laws or regulations, or changes in the interpretation of laws or regulations by a regulatory authority, specific to the use of AI, may decrease our revenues and earnings and may require us to change the manner in which we conduct some aspects of our business. In addition, our business and operations are subject to various U.S. federal, state, and local, and foreign, consumer protection laws, including laws which place restrictions on the use of automated and non-automated tools and technologies to communicate with wireless telephone subscribers or consumers generally.

The Company is subject to various laws and regulations at the local, state, and U.S. federal laws as well as laws in Europe and Israel that govern, and may restrict, communications via emails, calls, faxes, SMS text messages or communications done by bots. While the Company has taken steps to mitigate our liability for violations of the laws restricting the use of electronic communication tools, no assurance can be given that we will not be exposed to civil litigation or regulatory enforcement. We could face allegations that we have violated laws, rules and regulations, and even if these allegations are without merit, we could face regulatory inquiries, lawsuits and related defense costs, liability (such as fines, damages, consent decrees, and injunctions), harm to our reputation and other losses that could harm our business.

Further, to the extent that any changes in law or regulation further restrict the ways in which we communicate with prospective or current customers before or during onboarding, customer care, or claims management, these restrictions could result in a material reduction in our customer acquisition and retention, reducing the growth prospects of our business, and adversely affecting our financial condition and future cash flows.

Our success depends on our ability to attract consumers to our website and our online app and convert them into customers in a cost-effective manner. We depend, in large part, on search engines, social media platforms, digital app stores, content-based online advertising and other online sources for traffic to our website and our online app.

We rely on both paid and free algorithmic search listings; consequently, any modification to our relationships with search providers or changes in their display methodologies could increase our expenses or reduce our prominence in search results. Such shifts, along with the increasing use of ad-blocking software by consumers, could lead to a material decline in traffic to our website and app, adversely affecting our business and operating results.

Shifting regulations and commercial practices may restrict the ability of major digital platforms like Google and social media platforms like Meta to collect and monetize user data for targeted advertising. This proposed legislation could mandate annual SEC disclosures regarding the aggregate value of user data and specific revenue-generation models. Any resulting increase in advertising costs may force us to allocate additional marketing spend, potentially harming our operating results. Similarly, heightened scrutiny of insurance distribution may limit our reliance on third-party platforms, such as the Lemonade API, if those partners are unable to comply with evolving insurance laws and regulations.

Our ability to market and distribute our insurance products depends on maintaining cost-effective, satisfactory relationships with Apple and Google, as most of our customers access our services exclusively through their respective app stores. Both Apple and Google have broad discretion to change their respective terms and conditions applicable to the distribution of our online app, including those relating to the amount of (and requirement to pay) certain fees associated with purchases facilitated by Apple and Google through our online app, to interpret their respective terms and conditions in ways that may limit, eliminate or otherwise interfere with our ability to distribute online app through their stores, the features we provide and the manner in which we market in-app products. We cannot be certain that Apple or Google will not limit, eliminate or otherwise interfere with the distribution of our online app, the features we provide and the manner in which we market our online app. To the extent either or both of them do so, our business, results of operations and financial condition could be adversely affected.

In connection with running our business, we receive, store, use and otherwise process information that relates to individuals and/or constitutes “personal data,” “personal information,” “personally identifiable information,” or similar terms under applicable data privacy laws (collectively, “Personal Information”), including from and about actual and prospective customers, as well as our employees and business contacts. We also depend on third party vendors in relation to the operation of our business, a number of which process personal information on our behalf.

We and our vendors are subject to a variety of federal, state [and foreign] data privacy laws, rules, regulations, industry standards and other requirements, including those that apply generally to the processing of Personal Information, and those that are specific to certain industries, sectors, contexts, or locations. These requirements, and their application, interpretation and amendment are constantly evolving. It is also possible that new laws, regulations and other requirements, or amendments to or changes in interpretations of existing laws, regulations and other requirements, may require us to incur significant costs, implement new processes, or change our processing of information and business operations, which could ultimately hinder our ability to grow our business by extracting value from our data assets.

For example, the CCPA requires businesses that process personal information of California residents to, among other things: provide certain disclosures to California residents regarding the business’s collection, use, and disclosure of their personal information; receive and respond to requests from California residents to access, delete, and correct their personal information, or to opt-out of certain disclosures of their personal information; and enter into specific contractual provisions with service providers that process California resident personal information on the business’s behalf.

The enactment of the CCPA is prompting a wave of similar legislative developments in other states in the United States, which creates a patchwork of overlapping but different state laws. For example, since the CCPA went into effect, comprehensive privacy statutes that share similarities with the CCPA are now in effect and enforceable in numerous states, and will soon be enforceable in several other states as well. Similar laws have been proposed in many other states and at the federal level as well. Other state privacy laws have exempted from compliance financial institutions regulated under the Gramm-Leach-Bliley Act (the “GLBA”). A small number of states, including California, exempt only personal information collected pursuant to the GLBA, leaving a gap where the state law could apply where the company collects non-GLBA regulated information. However, other than California, those states have exempted insurance companies from compliance with the state privacy law. It is possible that more states will pass laws that regulate Lemonade similarly to California. The effects of the privacy laws are potentially significant and may require us to modify our data processing practices and policies and to incur substantial costs and potential liability in an effort to comply with such legislation.

Further, we are considered a “financial institution” under the GLBA. The GLBA regulates, among other things, the use of certain information about individuals (“non-public personal information”) in the context of the provision of financial services, including by insurance companies and other financial institutions. The GLBA includes both a “Privacy Rule,” which imposes obligations on financial institutions relating to the use or disclosure of non-public personal information, and a “Safeguards Rule,” which imposes obligations on financial institutions and, indirectly, their service providers to implement and maintain physical, administrative and technological measures to protect the security of non-public personal financial information. Any failure to comply with the GLBA could result in substantial financial penalties.

As we continue to expand into Europe and the UK, we may also face particular privacy, data security, and data protection risks in connection with requirements of the GDPR and other data protection regulations. The GDPR imposes comprehensive data privacy compliance obligations in relation to our collection, processing, sharing, disclosure, transfer and other use of data relating to an identifiable living individual or “personal data” , including a principal of accountability and the obligation to demonstrate compliance through policies, procedures, training and audit. Any failure or perceived failure to comply with these rules may result in regulatory fines or penalties including orders that require us to change the way we process data (including by way of our algorithms). In the event of a data breach, we are also subject to breach notification laws in the jurisdictions in which we operate, including U.S. state laws and the GDPR, and the risk of litigation and regulatory enforcement actions. In addition, a number of federal and state laws and regulations relating to privacy affect and apply to the insurance industry specifically, including those imposed by the NYDFS. See "Business - Regulation."

Additionally, we are subject to the terms of our privacy policies and privacy-related obligations to third parties. Any failure or perceived failure by us to comply with our privacy policies, our privacy-related obligations to customers or other third parties, or our privacy-related legal obligations, or any compromise of security that results in the unauthorized release or transfer of sensitive information, which could include Personal Information or other user data, may result in governmental or regulatory investigations, enforcement actions, regulatory fines, compliance orders, litigation or public statements against us by consumer advocacy groups or others, and could cause customers to lose trust in us, all of which could be costly and have an adverse effect on our business. In addition, new and changed rules and regulations regarding privacy, data protection (in particular those that impact the use of artificial intelligence) and cross-border transfers of Personal Information could cause us to delay planned uses and disclosures of data to comply with applicable privacy and data protection requirements. Moreover, if third parties that we work with violate applicable laws or our policies, such violations also may put Personal Information at risk, which may result in increased regulatory scrutiny and have a material adverse effect to our reputation, business and operating results.

We employ third-party licensed software for use in our business, and the inability to maintain these licenses, errors in the software we license or the terms of open source licenses could result in increased costs or reduced service levels, which would adversely affect our business.

Our business relies on certain third-party software obtained under licenses from other companies. We anticipate that we will continue to rely on such third-party software in the future. Although we believe that there are commercially reasonable alternatives to the third-party software we currently license, this may not always be the case, or it may be difficult or costly to replace. In addition, integration of new third-party software may require significant work and require substantial investment of our time and resources. Our use of additional or alternative third-party software would require us to enter into license agreements with third parties, which may not be available on commercially reasonable terms or at all. Many of the risks associated with the use of third-party software cannot be eliminated, and these risks could negatively affect our business.

Additionally, the software powering our technology systems incorporates software covered by open source licenses. The terms of many open source licenses have not been interpreted by U.S. courts, and there is a risk that the licenses could be construed in a manner that imposes unanticipated conditions or restrictions on our ability to operate our systems. In the event that portions of our proprietary software are determined to be subject to an open source license, we could be required to publicly release the affected portions of our source code or re-engineer all or a portion of our technology systems, each of which could reduce or eliminate the value of our technology systems. Such risk could be difficult or impossible to eliminate and could adversely affect our business, financial condition, and results of operations.

By processing certain personal injury data on behalf of our clients, we may be subject to specific compliance obligations under privacy and data security-related laws specific to the protection of healthcare information. Although we may be subject to the Health Insurance Portability and Accountability Act, the Health Information Technology for Economic and Clinical Health Act, and related state laws, we do not have a process in place to assess or align our privacy and security practices specifically against requirements for protecting medical information.

Our success depends upon the continued service of our co-founders, Daniel Schreiber and Shai Wininger (our "Co-Founders"), as Chief Executive Officer and President, respectively, and senior management team, highly-specialized insurance experts and key technical employees, as well as our ability to continue to attract and retain additional highly qualified personnel. If we are unable to attract the requisite personnel, our business and prospects may be adversely affected. Each of our Co-Founders, executive officers, specialized insurance experts and key technical personnel could terminate his or her relationship with us at any time which may delay or prevent the achievement of our strategic business objectives and could harm our business. Competition in our industry for qualified employees is intense. Our compensation arrangements, such as our equity award programs, may not always be successful in attracting new employees and retaining and motivating our existing employees. Moreover, if and when the stock options or other equity awards are substantially vested, employees under such equity arrangements may be more likely to leave, particularly when the underlying shares have seen a value appreciation.

We face competition for personnel and to attract top talent, we offer, and will need to continue to offer, competitive compensation and benefits packages. We may also need to increase our employee compensation levels. Failure to hire quickly, manage staffing needs, or successfully integrate new employees could diminish our efficiency, productivity, and morale, while impairing our ability to meet forecasts and retain talent, which in turn could have an adverse effect on our business, results of operations and financial condition.

We maintain offices in Israel and some of our officers, employees and directors are located in Israel, including our Co-Founders and some of our product development staff, help desk and online sales support operations. As of December 31, 2025, we had approximately 310 full-time employees in Israel. Although we do not currently sell our insurance products in Israel, political, economic and military conditions in Israel and the surrounding region may directly affect our Israeli operations. In recent years, including most recently after the events in October 2023, Israel has been involved in sporadic armed conflicts with (i) the Islamic Republic of Iran, (ii) Hamas, an Islamist terrorist group that controls the Gaza Strip, (iii) Hezbollah, an Islamist terrorist group that controls large portions of Southern Lebanon, (iv) Iranian-backed military forces in Syria and (v) the Houthis, an Islamist terrorist group that controls significant portions of Yemen. Some of these hostilities were accompanied by missile strikes against civilian targets in various parts of Israel, including areas in which our officers, employees and directors are located, and negatively affected conditions in Israel. As of December 31, 2025, the tension between Israel and Iran and/or these groups persist and could intensify in the future, which could materially and adversely affect conditions in Israel in general and our operations in particular.

Furthermore, many Israeli citizens are obligated to perform several days, and in some cases more, of annual military reserve duty each year until they reach the age of 40 (or older, for reservists who are military officers or who have certain occupations) and, in the event of a military conflict, may be called to active duty. In response to the recent hostilities as mentioned above, there have been call-ups of military reservists and it is possible that there will be increases in military reserve duty call-ups in the future. Some of our officers and employees based in Israel have been called upon to perform military reserve duty and/or active duty, and others may be called in the future. Our operations have been and may continue to be partially disrupted by these employee absences, which could materially adversely affect our business and results of operations. We have contingency plans and structures in place to mitigate these risks, and we continue to monitor our ongoing activities and will make any needed adjustments to ensure the continuity of our business, while supporting the safety and well-being of our employees.

If regional security conditions intensify, our suppliers in Israel could be affected, whether through workforce shortages caused by military reserve-duty mobilizations or disruptions to shipping lanes resulting from ongoing hostilities. Such disruptions could, in turn, affect our operations in Israel.

Parties with whom we do business may sometimes decline to travel to Israel during periods of heightened unrest or tension, forcing us to make alternative arrangements when necessary to meet our business partners in person. Further, shifting economic and political conditions in the United States and in other countries may result in changes in how the United States and other countries conduct business and other relations with Israel, which may have an adverse impact on our Israeli operations and a material adverse impact on our business. In addition, several countries, principally in the Middle East, restrict doing business with Israel, and additional countries may impose restrictions on doing business with Israel and Israeli companies whether as a result of hostilities in the region or otherwise. Moreover, there have been increased efforts by organizations and movements to cause companies and consumers to boycott Israeli goods based on Israeli government policies. Any hostilities, armed conflicts or political instability involving Israel could adversely affect our results of operations. With regards to the recent hostilities, there is still uncertainty regarding the extent to which it will impact our operations in Israel, which we continue to evaluate.

Our commercial insurance may not cover losses that could occur as a result of events associated with the security situation in the Middle East. Any losses or damages incurred by us could have a material adverse effect on our business. Continued hostilities between Israel and its neighbors and any future armed conflict, terrorist activity or political instability in the region could adversely affect our operations in Israel and adversely affect the market price of our common stock. An escalation of tensions or violence might result in a significant downturn in the economic or financial condition of Israel, which could have a material adverse effect on our operations in Israel and our business.

In addition, the Israeli government has recently and may in the future pursue extensive changes to Israel’s judicial system. In response to such changes, many individuals, organizations and institutions, both within and outside of Israel, have in the past and may in the future voice concerns that the proposed changes may negatively impact the business environment in Israel, due to potential reluctance of foreign investors to invest or transact business in Israel, increased currency fluctuations, downgrades in credit rating, increased interest rates, increased volatility in securities markets, and other changes in macroeconomic conditions.

To the extent that any of these negative developments occur, they may have an adverse effect on our business, our results of operations, or our ability to raise additional funds, if deemed necessary by our management and board of directors.

We enter into assignment of invention agreements with employees and consultants, pursuant to which such individuals assign to us all rights to any inventions created in the scope of their employment or engagement with us. Under the Israeli Patent Law, 5727-1967 (the "Israel Patent Law"), inventions conceived by an employee or a person deemed to be an employee (for example a consultant that was deemed to be an employee by the Israeli labor courts) during and in consequence of their employment are regarded as "service inventions," which belong to the employer, absent a specific agreement between employee and employer. Nevertheless, in the case of a service invention, employees and former employees may petition the Israeli Compensation and Royalties Committee established under the Israel Patent Law to determine whether they are entitled to remuneration for their service inventions. Although in the assignment of invention agreements with our employees they agree to waive their right to any additional compensation with respect to the service inventions, the Israeli Compensation and Royalties Committee and the Supreme Court have held that employees may be entitled to remuneration for their service inventions despite having waived such rights, resulting in uncertainty under Israeli law with respect to the efficacy of waivers of service invention rights. As such, we may face claims demanding remuneration in consideration for assigned service inventions, and as a consequence of such claims, we could be required to pay additional remuneration or royalties to our current or former employees (or consultants that might be deemed as employees), or be forced to litigate such claims, which could negatively affect our business.

We believe that our company culture has been critical to our success. Our status as a Certified B Corp and commitment to charitable giving distinguish us from our competitors and promote a relationship among our employees and customers founded on trust. We not only seek to engender a trusting relationship between our brand and our customers, but also among our employees. Our ability to continue to cultivate and maintain this culture is essential to our growth and continued success. We face a number of challenges that may affect our ability to sustain our corporate culture, including:

•failure to identify, attract, reward and retain people in leadership positions in our organization who share and further our culture, values and mission;

•the increasing size and geographic diversity of our workforce, and our ability to promote a uniform and consistent culture across all our offices and employees;

•the market perception about our charitable contributions and social and political stances;

•competitive pressures to move in directions that may divert us from our mission, vision and values;

•the continued challenges of a rapidly-evolving industry; and

•the increasing need to develop expertise in new areas of business that affect us.

Our unique culture is one of our core characteristics that helps us to attract and retain key personnel. If we are not able to maintain our culture, we would have to incur additional costs and find alternative methods to recruit key employees, which in turn could cause our business, results of operations and financial condition to be adversely affected.

Approximately 45% of our gross written premium for the year ended December 31, 2025 originated from customers in California, New York, and Texas. As a result of this concentration, if a significant catastrophe event or series of such events occurs and causes material loss in California, New York and Texas, our business, financial condition and results of operation could be materially adversely affected. For example, the January 2025 California Wildfires resulted in net incurred losses of $19.6 million and a California FAIR Plan assessment of $6.9 million. As a result of our concentration in this key market, any adverse changes in the regulatory environment affecting property and casualty insurance in California, New York and Texas may expose us to more significant risks. Further, as compared to our competitors who operate on a wider geographic scale, any adverse changes in the regulatory environment affecting property and casualty insurance in California, New York and Texas may expose us to more significant risks.

Our success is dependent in part on protecting our intellectual property rights and technology (such as source code, information, data, processes and other forms of information, knowhow and technology). We rely on a combination of copyrights, trademarks, service marks, trade secret laws and contractual restrictions to establish and protect our intellectual property. However, there are steps that we have not yet taken to protect our intellectual property on a global basis. Additionally, the steps that we have already taken to protect our intellectual property may not be sufficient or effective. Even if we do detect violations, we may need to engage in litigation to enforce our rights.

While we take precautions designed to protect our intellectual property, it may still be possible for competitors and other unauthorized third parties to copy our technology and use our proprietary brand, content and information to create or enhance competing solutions and services, which could adversely affect our competitive position in our rapidly evolving and highly competitive industry. Some license provisions that protect against unauthorized use, copying, transfer and disclosure of our technology may be unenforceable under the laws of certain jurisdictions and foreign countries. We enter into confidentiality and invention assignment agreements with our employees and consultants and enter into confidentiality agreements with our third-party providers and strategic partners. We cannot assure you that these agreements will be effective in controlling access to, and use and distribution of, our platform and proprietary information. Further, these agreements do not prevent our competitors from independently developing technologies that are substantially equivalent or superior to our offerings. Such arrangements may limit our ability to protect, maintain, enforce or commercialize such intellectual property rights, including requiring agreement with or payment to our joint development partners before protecting, maintaining, licensing or initiating enforcement of such intellectual property rights, and may allow such joint development partners to register, maintain, enforce or license such intellectual property rights in a manner that may affect the value of the jointly-owned intellectual property or our ability to compete in the market.

We have filed, and may continue in the future to file, applications to protect certain of our innovations and intellectual property. We do not know whether any of our applications will result in the issuance of a patent, trademark or copyright, as applicable, or whether the examination process will require us to narrow our claims. In addition, we may not receive competitive advantages from the rights granted under our intellectual property. Our existing intellectual property, and any intellectual property granted to us or that we otherwise acquire in the future, may be contested, circumvented or invalidated, and we may not be able to prevent third parties from infringing our rights to our intellectual property. Therefore, the exact effect of the protection of this intellectual property cannot be predicted with certainty. In addition, given the costs, effort, risks and downside of obtaining patent protection, including the requirement to ultimately disclose the invention to the public, we may choose not to seek patent protection for certain innovations. Any failure to adequately obtain such patent protection, or other intellectual property protection, could later prove to adversely impact our business.

We currently hold various domain names relating to our brand, including Lemonade and Lemonade.com. Failure to protect our domain names could adversely affect our reputation and brand and make it more difficult for users to find our website and our online app. We may be unable, without significant cost or at all, to prevent third parties from acquiring domain names that are similar to, infringe upon or otherwise decrease the value of our trademarks and other proprietary rights.

We may be required to spend significant resources in order to monitor and protect our intellectual property rights, and some violations may be difficult or impossible to detect. Litigation to protect and enforce our intellectual property rights could be costly, time-consuming and distracting to management and could result in the impairment or loss of portions of our intellectual property. Our efforts to enforce our intellectual property rights may be met with defenses, counterclaims and countersuits attacking the validity and enforceability of our intellectual property rights. Our inability to protect our proprietary technology against unauthorized copying or use, as well as any costly litigation or diversion of our management's attention and resources, could impair the functionality of our platform, delay introductions of enhancements to our platform, result in our substituting inferior or more costly technologies into our platform or harm our reputation or brand. In addition, we may be required to license additional technology from third parties to develop and market new offerings or platform features, which may not be on commercially reasonable terms or at all and could adversely affect our ability to compete.

If we are unable to prevent the unauthorized use or exploitation of our intellectual property, the value of our brand, content, and other intangible assets may be diminished, competitors may be able to more effectively mimic our service and methods of operations, the perception of our business and service to customers and potential customers may become confused, and our ability to attract customers may be adversely affected. Any inability or failure to protect our intellectual property could adversely impact our business, results of operations and financial condition.

Companies in the internet and technology industries are frequently subject to litigation based on allegations of infringement or other violations of intellectual property rights. In addition, certain companies and rights holders seek to enforce and monetize patents or other intellectual property rights they own, have purchased or otherwise obtained. As we gain an increasingly high public profile, the possibility of intellectual property rights claims against us grows. From time to time, third parties may assert claims of infringement of intellectual property rights against us. We may not be successful in defending against these allegations or reaching a business resolution that is satisfactory to us. Our competitors and others may now and in the future have significantly larger and more mature patent portfolios than us. In addition, future litigation may involve patent holding companies or other adverse patent owners who have no relevant product or service revenue and against whom our own patents may therefore provide little or no deterrence or protection. Many potential litigants, including some of our competitors and patent-holding companies, have the ability to dedicate substantial resources to assert their intellectual property rights. Any claim of infringement by a third party, even those without merit, could cause us to incur substantial costs defending against the claim, could distract our management from our business and could require us to cease use of such intellectual property. Furthermore, because of the substantial amount of discovery required in connection with intellectual property litigation, we risk compromising our confidential information during this type of litigation. We may be required to pay substantial damages, royalties or other fees in connection with a claimant securing a judgment against us, we may be subject to an injunction or other restrictions that prevent us from using or distributing our intellectual property, or from operating under our brand, or we may agree to a settlement that prevents us from distributing our offerings or a portion thereof, which could adversely affect our business, results of operations and financial condition.

With respect to any intellectual property rights claim, we may have to seek out a license to continue operations found to violate such rights, which may not be available on favorable or commercially reasonable terms and may significantly increase our operating expenses. Some licenses may be non-exclusive, and therefore our competitors may have access to the same technology licensed to us. If a third party does not offer us a license to its intellectual property on reasonable terms, or at all, we may be required to develop alternative, non-infringing technology, which could require significant time (during which we would be unable to continue to offer our affected offerings), effort and expense and may ultimately not be successful. Any of these events could adversely affect our business, results of operations and financial condition.

As of December 31, 2025, we had gross accumulated federal NOLs for tax purposes of $321.0 million, which can be offset against our future taxable income. Of these federal NOLs, $23.7 million in losses will begin to expire in 2036 and $297.3 million in losses can be carried forward indefinitely. As of December 31, 2025, the Company has gross accumulated state and local losses for tax purposes of $38.9 million which will begin to expire in 2030.

We may be unable to use our NOLs. Under Section 382 of the Code, if a corporation undergoes an "ownership change" (very generally defined as a greater than 50% change, by value, in the corporation's equity ownership by certain shareholders or groups of shareholders over a rolling three- year period), the corporation's ability to use its pre-ownership change NOLs to offset its post-ownership change income may be limited. We have experienced ownership changes in the past, and we may experience ownership changes in the future as a result of subsequent shifts in our stock ownership, some of which may be outside of our control. If we have undergone an ownership change, we may be prevented from fully utilizing our NOLs existing at the time of the ownership change prior to their expiration. Future regulatory changes could also limit our ability to utilize our NOLs. To the extent we are not able to offset future taxable income with our NOLs, our net income and cash flows may be adversely affected.

We conduct business globally and file income tax returns in multiple jurisdictions. Our consolidated effective income tax rate could be materially adversely affected by several factors, including: changing tax laws, regulations and treaties, or the interpretation thereof (such as the Inflation Reduction Act which, among other changes, introduced a 15% corporate minimum tax on certain United States corporations and a 1% excise tax on certain stock redemptions by United States corporations, and the One Big Beautiful Bill Act which, among other changes, expanded the rules related to deductibility of executive compensation, reinstated bonus depreciation deductions for qualified property, restored EBITDA-based business interest expense limitation and implemented changes relating to the computation of certain taxes in respect of non-US activities); tax policy initiatives and reforms in effect or under consideration (such as those related to the OECD/G20 Inclusive Framework on Base Erosion and Profit Sharing or other projects , including the “Pillar Two” framework to set a minimum global corporate tax rate of 15% which has been or may be implemented in many jurisdictions); the practices of tax authorities in jurisdictions in which we operate; and the resolution of issues arising from tax audits or examinations and any related interest or penalties. In January 2026, more than 145 countries in the OECD/G20 Inclusive Framework agreed to have U.S.-headquartered companies remain subject to only U.S. global minimum taxes while exempting them from Pillar Two. This side-by-side agreement recognizes the tax sovereignty of the United States over the worldwide operations of U.S. companies and the tax sovereignty of other countries over business activity within their own borders. However, the precise contours of this side-by-side agreement as well as the details about its implementation by specific jurisdictions are uncertain.

We are unable to predict what tax reforms may be proposed or enacted in the future or what effect such changes would have on our business, but such changes, to the extent they are brought into tax legislation, regulations, policies or practices in jurisdictions in which we operate, could increase the estimated tax liability that we have expensed to date and paid or accrued on our consolidated statements of operations and comprehensive loss, and otherwise affect our future results of operations, cash flows in a particular period and overall or effective tax rates in the future in countries where we have operations, reduce post-tax returns to our shareholders and increase the complexity, burden and cost of tax compliance.

Since we conduct limited operations in Israel, Europe and the UK, portions of our revenues, expenses, assets and liabilities are denominated in New Israeli Shekels, Euros and GBP pounds. Because our consolidated financial statements are presented in U.S. dollars, we must translate non-U.S. dollar denominated revenues, income and expenses, as well as assets and liabilities, into U.S. dollars at exchange rates in effect during or at the end of each reporting period. Therefore, increases or decreases in the value of the U.S. dollar against the other currencies may affect our revenues, income and the value of balance sheet items denominated in foreign currencies.

External events such as Brexit, global pandemics, the ongoing uncertainty regarding actual and potential shifts in U.S. and foreign, trade, economic and other policies, including under the current U.S. Presidential administration, the passage of U.S. taxation reform legislation, and concerns over interest rates (particularly short-term rates) each have caused, and may continue to cause, significant volatility in currency exchange rates, especially among the U.S. dollar, Euros and the GBP pounds. If global economic and market conditions, or economic conditions in the UK, European Union, the United States or other key markets remain uncertain or deteriorate further, the value of the GBP pounds and Euros, and the global credit markets may further weaken.

Historically, insurers have experienced significant fluctuations in operating results due to competition, frequency and severity of catastrophic events, levels of capacity, adverse litigation trends, regulatory constraints, general economic conditions, and other factors. The supply of insurance is related to prevailing prices, the level of insured losses and the level of capital available to the industry that, in turn, may fluctuate in response to changes in rates of return on investments being earned in the insurance industry. As a result, the insurance business historically has been a cyclical industry characterized by periods of intense price competition due to excessive underwriting capacity as well as periods when shortages of capacity increased premium levels. Demand for insurance depends on numerous factors, including the frequency and severity of catastrophic events, levels of capacity, the introduction of new capital providers and general economic conditions. All of these factors fluctuate and may contribute to price declines generally in the insurance industry.

We cannot predict with certainty whether market conditions will improve, remain constant or deteriorate. Negative market conditions may impair our ability to underwrite insurance at rates we consider appropriate and commensurate relative to the risk assumed. Additionally, negative market conditions could result in a decline in policies sold, an increase in the frequency of claims and premium defaults, and an uptick in the frequency of falsification of claims. If we cannot underwrite insurance at appropriate rates, our ability to transact business will be materially and adversely affected. Any of these factors could lead to an adverse effect on our business, results of operations and financial condition.

Our revenue and results of operations may vary significantly from period to period due to a variety of factors, some of which are outside of our control, including changes in the number of customers purchasing our products and fluctuations in the timing and amount of our expenses. The insurance industry, and particularly renters and homeowners insurance, is also subject to seasonal patterns and volatility, including weather-related events that may be seasonal and may result in variability in claims reporting and payment patterns. As a result, period-to-period comparisons of our operating results may not be meaningful, and the results of any single period should not be relied upon as an indication of future performance. If our results of operations do not meet the expectations of investors or research analysts, our stock price could be adversely affected.

We have experienced, and expect to continue to experience, seasonal fluctuations in revenues and growth rates driven by insurance purchasing patterns. For example, our revenues may be disproportionately higher in our third fiscal quarter due to seasonality in renter and homeowner move-in activity, which historically occurs in July, August, and September, and our growth may also be greater during that period. As our business expands and matures, additional seasonality trends may develop, and the seasonality and customer behavior we experience may change. Volatility in our key operating metrics, or failure to meet quarterly guidance or the expectations of research analysts or investors, could adversely affect our financial results and investor perceptions of our business prospects and cause our stock price to decline.

As of December 31, 2025, we were licensed to sell renters, homeowners, pet and/or car insurance policies in 50 states of the United States, and operate in 41 of those states, and Washington, D.C. We also hold a pan-European license, which enables us to sell in 30 countries across Europe, and currently operate in Germany, the Netherlands, France. In addition, we also hold branch authorization permits in the UK which allows us to operate on a permanent basis in the UK market.

In the United States, each state regulator retains the authority to license insurers in their states, and an insurer generally may not operate in a state in which it is not licensed. Accordingly, we are not permitted to sell insurance to residents of the remaining states and territories of the United States, which is likely to put us at a disadvantage among many of our competitors that have been in business much longer than us and are licensed to sell their insurance products in most, if not all, U.S. jurisdictions. We have a reinsurance captive subsidiary, Lemonade Re SPC, domiciled in the Cayman Islands which is subject to inspections by the Cayman Islands Monetary Authority.

We are subject to extensive regulation and supervision in the states in which we transact business by the individual state insurance departments. This regulation is generally designed to protect the interests of customers, and not necessarily the interests of insurers or agents, their shareholders or other investors. Numerous aspects of our insurance business are subject to regulation, including, but not limited to, premium rates, mandatory covered risks, limitations on the ability to renew or elect not to renew business, prohibited exclusions, licensing and appointment of agents, restrictions on the size of risks that may be insured under a single policy, reserves and provisions for unearned premiums, losses and other obligations, deposits of securities for the benefit of customers, investments and capital, policy forms and coverages, advertising and other conduct, including restrictions on the use of credit information and other factors in underwriting, as well as other underwriting and claims practices. To the extent we decide to expand our current product offerings to include other insurance products, this would subject us to additional regulatory requirements and scrutiny in each state in which we elect to offer such products. States have also adopted legislation defining and prohibiting unfair methods of competition and unfair or deceptive acts and practices in the business of insurance. Prohibited practices include, but are not limited to, misrepresentations, false advertising, coercion, disparaging other insurers, unfair claims settlement procedures, and discrimination in the business of insurance. Noncompliance with any of such state statutes may subject us to regulatory action by the relevant state insurance regulator, and, in certain states, private litigation. States also regulate various aspects of the contractual relationships between insurers and independent agents.

Such laws, rules and regulations are usually overseen and enforced by the various state insurance departments, as well as through private rights of action and by state attorneys general. Such regulations or enforcement actions are often responsive to current consumer and political sensitivities, such as homeowners insurance rates and coverage forms, or which may arise after a major event. Such rules and regulations may result in rate suppression, limit our ability to manage our exposure to unprofitable or volatile risks, or lead to fines, premium refunds or other adverse consequences. The federal government also may regulate aspects of our businesses, such as the protection of consumer confidential information or the use of consumer insurance (credit) scores to underwrite and assess the risk of customers under the Fair Credit Reporting Act ("FCRA"). Among other things, the FCRA requires insurance companies to have a permissible purpose before obtaining and using a consumer report for underwriting purposes, as well as comply with related notice and recordkeeping requirements. Failure to comply with federal requirements under the FCRA or any other applicable federal laws would subject us to regulatory fines and other sanctions. In addition, given our short operating history to-date and rapid speed of growth, we are particularly vulnerable to regulators identifying errors in the policy forms we use, the rates we charge, and our customer communications. As a result of such noncompliance, regulators could impose fines, rebates or other penalties, including cease-and-desist orders for an individual state, or all states, until the identified noncompliance is rectified.

Our ability to retain state licenses depends on our ability to meet licensing requirements established by the NAIC and adopted by each state, subject to variations across states. If we are unable to satisfy the applicable licensing requirements of any particular state, we could lose our license to do business in such state, which would result in the temporary or permanent cessation of our operations in that state. Alternatively, if we are unable to satisfy applicable state licensing requirements, we may be subject to additional regulatory oversight, have our license suspended, or be subject to seizure of assets. Any such events could adversely affect our business, results of operations or financial condition. See "Regulation — Required Licensing."

In addition, as a condition to writing business in certain states, insurers are required to participate in various pools or risk sharing mechanisms or to accept certain classes of risk, regardless of whether such risks meet their underwriting requirements for voluntary business. Some states also limit or impose restrictions on the ability of an insurer to withdraw from certain classes of business. New York, among other states, imposes significant restrictions on a company's ability to materially reduce its exposures or to withdraw from certain lines of business. The state insurance departments can impose significant charges on an insurer in connection with a market withdrawal or refuse to approve withdrawal plans on the grounds that they could lead to market disruption. Laws and regulations that limit cancellation and non-renewal of policies or that subject withdrawal plans to prior approval requirements may significantly restrict our ability to exit unprofitable markets.

Such actions and related regulatory restrictions may limit our ability to reduce our potential exposure to hurricane-related losses.

Our European insurance entities, Lemonade Insurance N.V., Lemonade Agency B.V. and Lemonade B.V., are subject to primary supervision by the Dutch Central Bank (De Nederlandsche Bank, "DNB") as the supervisory authority of its home member state, the Dutch Authority for the Financial Markets (Autoriteit Financiële Markten, "AFM"), and the German Federal Financial Supervisory Authority (Bundesanstalt für Finanzdienstleistungsaufsicht, "BaFin") as the supervisory authority of a host member state. DNB and AFM expect firms to avoid actions that jeopardize compliance with their statutory objectives and applicable rules and regulations and have extensive powers to intervene in the affairs of a regulated firm. When DNB is concerned that an insurer may present a risk, this may lead to negative consequences, including the requirement to maintain a higher level of regulatory capital (via capital "add-ons" under the Solvency II Directive) to match the higher perceived risks and enforcement action where the risks identified breach applicable rules and regulations. In the case of a breach of our license requirements or obligations arising from the applicable rules and regulations, we may be subject to the DNB and the AFM's sanctions, including (public) formal warnings, orders to adopt a certain course of conduct, incremental penalties and administrative fines, revocation of an undertaking license and, in the case of insurers, where the breach relates to material prudential shortcomings, emergency measures (including the appointment of an administrator or the imposition of measures aimed at winding-up the undertaking). Any such events could adversely affect our business, results of operations or financial condition. See "Business - Regulation - European Regulation.

We are subject to the insurance holding company laws of New York, Delaware and California, which require LIC and MIC to register with the NYDFS, DE Dept. and CDI, as applicable, and furnish information concerning the operations of companies within the holding company system that may materially affect the operations, management or financial condition of LIC and MIC. These statutes also provide that all transactions among members of a holding company system must be fair and reasonable and, if material or of specified types, such transactions require prior notice and approval or non-disapproval by the NYDFS, DE Dept. or the CDI, as applicable. These prior notification and approval requirements may result in business delays and additional business expenses. If we fail to comply with such requirements or fail to comply with other applicable insurance regulations in New York, Delaware or California, we may be subject to fines and penalties imposed by the applicable state insurance departments.

In the past decade, various state insurance regulators have increased their focus on risks within an insurer's holding company system that may pose enterprise risk to the insurer. In 2012, the NAIC adopted significant changes to the insurance holding company act and regulations (the "NAIC Amendments"). The NAIC Amendments, when adopted by the various states, are designed to respond to perceived gaps in the regulation of insurance holding company systems in the United States. One of the major changes is a requirement that an insurance holding company system's ultimate controlling person submit annually to its lead state insurance regulator an "enterprise risk report" that identifies activities, circumstances or events involving one or more affiliates of an insurer that, if not remedied properly, are likely to have a material adverse effect upon the financial condition or liquidity of the insurer or its insurance holding company system as a whole. Other changes include requiring a controlling person to submit prior notice to its domiciliary insurance regulator of a divestiture of control, having detailed minimum requirements for cost sharing and management agreements between an insurer and its affiliates and expanding of the agreements between an insurer and its affiliates to be filed with its domiciliary insurance regulator. The NAIC Amendments must be adopted by the individual state legislatures and insurance regulators in order to be effective. New York State, Delaware and California include a form of the enterprise risk report requirement.

Various other regulations may also be enacted by states, including the ORSA Model Act as described in “Business - Regulation”. We cannot predict the impact, if any, that the NAIC Amendments, compliance with the ORSA Model Act, or any other regulatory requirements may have on our business, financial condition or results of operations. See "Business - Regulation”.

In response to the growing threat of cyber-attacks in the insurance industry, certain jurisdictions, including New York, have begun to consider new cybersecurity measures, including the adoption of cybersecurity regulations. In March 2017, the NYDFS promulgated Cybersecurity Requirements for Financial Services Companies, which requires covered financial institutions, including LIC, to establish and maintain a cybersecurity program and implement and maintain cybersecurity policies and procedures with specific requirements. On November 1, 2023, the NYDFS amended the Cybersecurity Requirements for Financial Services Companies to expand such requirements and add new obligations. Additionally, on October 24, 2017, the NAIC adopted its Insurance Data Security Model Law, intended to serve as model legislation for states to enact in order to govern cybersecurity and data protection practices of insurers, insurance agents, and other licensed entities registered under state insurance laws. More than half of the United States have adopted versions of the NAIC Insurance Data Security Model Law, each with a different effective date, and other states may adopt versions of the NAIC Insurance Data Security Model Law in the future.

In the EU, we are subject to the requirements of the Digital Operational Resilience Act (DORA) which became applicable as of January 2025. DORA aims to ensure that financial entities better manage ICT (Information Communication Technologies) risks and become more resilient to cyber threats and ICT disruptions. To this end, DORA contains various requirements, including for managing the risks arising from the use of ICT third party service providers. Although we take steps to comply with financial industry cybersecurity regulations and believe we are materially compliant with their requirements, our failure to comply with new or existing cybersecurity regulations could result in regulatory actions and other penalties. Any perceived non-compliance may result in regulatory scrutiny, and if found to be non-compliant, significant fines and corrective orders under DORA (and, where applicable, criminal penalties under Member State national law), See "Business - Regulation of Enterprise Risk, Cybersecurity, and Other Recent Developments".

Increased frequency or severity of natural disasters, severe weather, catastrophes and other events could drive higher claims, limit our ability to manage exposures, reduce capital available to write new business, and increase reliance on reinsurance that may be unavailable or unaffordable, or may not perform as expected. Various weather and natural events may also affect insurance and reinsurance pricing and availability and the value of our investment portfolio. Pandemics and other public health events can disrupt economies and markets, increase claims and fraud, and reduce customers’ ability to pay premiums. In addition, evolving and fragmented climate‑related laws, regulations, and transition policies across jurisdictions may increase compliance costs and require operational or capital expenditures In addition, governmental and regulatory responses to these events—including new or changing laws, regulations, and enforcement priorities—may increase our compliance and administrative costs, restrict our underwriting or pricing flexibility, and otherwise adversely affect our business and financial condition.

Heightened or shifting scrutiny by regulators, investors, employees, clients, and other stakeholders regarding ESG matters—such as environmental stewardship, climate change, human capital management, responsible use of artificial intelligence, and cybersecurity and data privacy—could increase our costs (including compliance, monitoring, reporting, and stakeholder engagement), harm our reputation, and adversely affect our business performance. If we do not, or are not perceived to, adequately address these matters or demonstrate progress toward current or future ESG goals, negative publicity (including on social media) could damage our reputation and our relationships with regulators and the communities in which we operate, and could reduce employee engagement and retention and customers’ willingness to do business with us.

ESG-related regulation and disclosure requirements are evolving and have received increased attention in the United States, the European Union, and the United Kingdom. Divergent, changing, or conflicting requirements across or within jurisdictions (including between U.S. federal and state regimes) may create a complex and fragmented regulatory landscape and increase the risk, burden, and cost of compliance. In addition, there has been an increase in activism and litigation in opposition to certain ESG or human capital management initiatives. To the extent we are subject to such activism or challenges, it may require us to incur additional costs or otherwise adversely affect our business.

Stakeholder expectations may diverge, and we may face criticism for the content, extent, or pace of our ESG initiatives, as well as for adopting ESG practices at all, including in jurisdictions considering or enacting “anti-ESG” policies or legislation. Actual or perceived shortcomings in our ESG practices or disclosures, or a failure to manage stakeholder expectations, could erode trust, harm our reputation, subject us to shareholder activism or litigation, and adversely affect our business, financial condition, results of operations, and cash flows.

Third-party and investor-developed ESG ratings and scoring frameworks are widely publicized and may influence investment and voting decisions. Unfavorable ratings of the Company or our industry, or exclusion from ESG-oriented investment funds, could negatively affect investor sentiment, divert investment to other issuers or sectors, and adversely impact our stock price and our access to, and cost of, capital.

We use data, technology and intellectual property licensed from unaffiliated third parties in certain of our products, including insurance industry proprietary information that we license from Insurance Services Office, Inc. ("ISO"), and we may license additional third-party technology and intellectual property in the future. Any errors or defects in this third-party technology and intellectual property could result in errors that could harm our brand and business. In addition, licensed technology and intellectual property may not continue to be available on commercially reasonable terms, or at all. Also, should ISO refuse to license its proprietary information to us on the same terms that it offers to our competitors, we could be placed at a significant competitive disadvantage.

Further, although we believe that there are currently adequate replacements for the third-party technology and intellectual property we presently use other than proprietary information provided by ISO, the loss of our right to use any of this technology and intellectual property could result in delays in producing or delivering affected products until equivalent technology or intellectual property is identified, licensed or otherwise procured, and integrated. Our business would be disrupted if any technology and intellectual property we license from others or functional equivalents of this software were either no longer available to us or no longer offered to us on commercially reasonable terms. In either case, we would be required either to attempt to redesign our products to function with technology and intellectual property available from other parties or to develop these components ourselves, which would result in increased costs and could result in delays in product sales and the release of new product offerings. Alternatively, we might be forced to limit the features available in affected products. Any of these results could harm our business, results of operations and financial condition.

Along with others in the insurance industry, models developed internally and by third party vendors are used along with our own historical data in assessing property insurance exposure to catastrophe losses. These models assume various conditions and probability scenarios; however, they do not necessarily accurately predict future losses or measure losses currently incurred. Further, the accuracy of such models may be negatively impacted by changing climate conditions. Catastrophe models use historical information and scientific research about natural events, such as hurricanes and earthquakes, as well as detailed information about our in-force business. This information is used in connection with pricing and risk management activities. However, since actual catastrophic events vary considerably, there are limitations with respect to its usefulness in predicting losses in any reporting period. Other limitations are evident in significant variations in estimates between models, material increases and decreases in results due to model changes and refinements of the underlying data elements and actual conditions that are not yet well understood or may not be properly incorporated into the models.

We currently rely on third-party vendors to provide payment processing services, including the processing of payments from credit cards and debit cards, and our business would be disrupted if these vendors become unwilling or unable to provide these services to us and we are unable to find a suitable replacement on a timely basis. If we or our processing vendor fail to maintain adequate systems for the authorization and processing of credit card transactions, it could cause one or more of the major credit card companies to disallow our continued use of their payment products. In addition, if these systems fail to work properly and, as a result, we do not charge our customers' credit cards on a timely basis or at all, our business, revenue, results of operations and financial condition could be harmed.

The payment methods that we offer also subject us to potential fraud and theft by criminals, who are becoming increasingly more sophisticated, seeking to obtain unauthorized access to or exploit weaknesses that may exist in the payment systems. If we fail to comply with applicable rules or requirements for the payment methods we accept, or if payment-related data are compromised due to a breach of data, we may be liable for significant costs incurred by payment card issuing banks and other third parties or subject to fines and higher transaction fees, or our ability to accept or facilitate certain types of payments may be impaired. In addition, our customers could lose confidence in certain payment types, which may result in a shift to other payment types or potential changes to our payment systems that may result in higher costs. If we fail to adequately control fraudulent credit card transactions, we may face civil liability, diminished public perception of our security measures, and significantly higher credit card-related costs, each of which could harm our business, results of operations and financial condition.

We provide renters, homeowners, pet, life and car insurance products through our website and our online app that compete with traditional offline counterparts. We do not generally offer insurance through traditional, offline brokers. We believe that the continued growth and acceptance of online products and services generally will depend, to a large extent, on the continued growth in commercial use of the internet and the continued migration of traditional offline markets and industries online.

Purchasers of insurance may develop the perception that purchasing insurance products online is not as effective as purchasing such products through a broker or other traditional offline methods, and the homeowners and renters insurance markets may not migrate online as quickly as (or at the levels that) we expect. Moreover, if, for any reason, an unfavorable perception develops that data automation, artificial intelligence and/or bots are less efficacious than traditional offline methods of purchasing insurance, underwriting, claims processing, and other functions that use data automation, artificial intelligence and/or bots, our business, results of operations and financial condition could be adversely affected.

Our results of operations and financial condition depend, in part, on the adequacy of our loss and loss adjustment expense (“LAE”) reserves. These reserves are estimates and are inherently uncertain; actual claim payments and related expenses may differ, potentially materially, from the amounts we have recorded.

Our reserve estimates are based on, among other things, reported claims, assumptions regarding future claim frequency and severity, inflation, catastrophe activity (including severe weather and the effects of climate change), economic conditions, and developments in the legal, judicial, and regulatory environment, including changes in laws, litigation trends, and judicial interpretations of coverage and liability. Our estimates also depend on actuarial methods and models (including those that assume historical loss development patterns will continue), as well as operational factors such as claims handling and settlement practices, product mix, policy terms and conditions, loss management programs, and changes in claim reporting patterns.

We regularly review and update our reserves as new information becomes available and as assumptions, methods, and practices are refined. Nevertheless, there can be no assurance that our reserves will prove adequate. If our reserves are insufficient for any reason, we may be required to increase reserves, which would reduce net income and stockholders’ equity in the period the deficiency is identified and could adversely affect future earnings, liquidity, and financial strength ratings. Any such adverse effects could also impair our ability to write new business, retain existing customers, or obtain reinsurance on acceptable terms.

Our insurance subsidiaries are subject to risk-based capital standards and other minimum capital and surplus requirements imposed under the laws of the State of New York and Delaware, respectively. The risk-based capital standards, based upon the Risk-Based Capital Model Act adopted by the NAIC, require our insurance subsidiaries to report their results of risk-based capital calculations to the NYDFS, or DE Dept., as applicable and the NAIC. These risk-based capital standards provide for different levels of regulatory attention depending upon the ratio of an insurance company's total adjusted capital, as calculated in accordance with NAIC guidelines, to its authorized control level risk-based capital. Authorized control level risk-based capital is determined using the NAIC's risk-based capital formula, which measures the minimum amount of capital that an insurance company needs to support its overall business operations.

An insurance company with total adjusted capital that is less than 200% of its authorized control level risk-based capital is at a company action level, which would require the insurance company to file a risk-based capital plan that, among other things, contains proposals of corrective actions the Company intends to take that are reasonably expected to result in the elimination of the Company action level event. Additional action level events occur when the insurer's total adjusted capital falls below 150%, 100%, and 70% of its authorized control level risk-based capital. The lower the percentage, the more severe the regulatory response, including, in the event of a mandatory control level event (total adjusted capital falls below 70% of the insurer's authorized control level risk-based capital), placing the insurance company into receivership. As of December 31, 2025, our risk-based capital ratio was 586% for LIC and 625% for MIC.

Our wholly-owned, Cayman Islands-based captive reinsurer, Lemonade Re SPC, is subject to capital and other regulatory requirements imposed by the Cayman Islands Monetary Authority (“CIMA”). Although these capital requirements are generally less constraining than U.S. capital requirements, failure to satisfy these requirements could result in regulatory actions from the CIMA or loss of or modification of Lemonade Re SPC’s insurer license, which could adversely impact our ability to improve our overall capital efficiency.

Our insurance subsidiaries in Europe are subject to prudential solvency and minimum capital requirements under the Solvency II framework as implemented in their local jurisdictions, including related governance and reporting obligations.

In addition, our insurance subsidiaries are required to maintain certain minimum capital and surplus and to limit its written premiums to specified multiples of its capital and surplus. The insurance subsidiaries could exceed these ratios if its volume increases faster than anticipated or if its surplus declines due to catastrophe or non-catastrophe losses or excessive underwriting and operational expenses.

Any failure by our insurance subsidiaries to meet the applicable risk-based capital or minimum statutory capital requirements or the writings ratio limitations imposed by the laws of the State of New York or Delaware, as applicable (or other states where currently or may in the future conduct business), or Solvency II and minimum capital requirements applicable to our insurance subsidiaries in Europe, could subject them to further examination or corrective action imposed by regulators, including limitations on our writing of additional business, state supervision, or liquidation.

Any changes in existing risk-based capital requirements, minimum statutory capital requirements, or applicable writings ratios may require us to increase our statutory capital levels, which we may be unable to do. See "Business - Regulation of Our Business — Risk-Based Capital." The insurance laws of many states subject property and casualty insurers doing business in those states to statutory property and casualty guaranty fund assessments.

The purpose of a guaranty fund is to protect customers by requiring that solvent property and casualty insurers pay the insurance claims of insolvent insurers. These guaranty associations generally pay these claims by assessing solvent insurers proportionately based on each insurer's share of voluntary premiums written in the state. While most guaranty associations provide for recovery of assessments through subsequent rate increases, surcharges or premium tax credits, there is no assurance that insurers will ultimately recover these assessments, which could be material, particularly following a large catastrophe or in markets which become disrupted.

Maximum contributions required by law in any one year vary by state. We cannot predict with certainty the amount of future assessments because they depend on factors outside our control, such as insolvencies of other insurance companies. Significant assessments could have a material adverse effect on our financial condition and results of operations. See "Business - Regulation of Our Business — Insolvency Funds and Associations, Mandatory Pools, and Insurance Facilities."

Our insurance subsidiary, LIC, currently has a Financial Stability Rating ("FSR") of 'A' Exceptional from Demotech, Inc., where insurers with this rating are expected to have a positive surplus at least 18 months from the initial date of rating assignment. Demotech, Inc. is a financial analysis firm that provides FSRs as well as consulting services for property and casualty insurance companies and title underwriters. Demotech, Inc. provides financial stability ratings to insurance companies of all sizes. When providing a rating, Demotech, Inc. evaluates total assets, liabilities, revenues and expenses, working capital, administrative expenses, net income, surplus, receivables, amount of business written, industry focus and business model, among others.

While our Demotech, Inc. rating has proved satisfactory to date, we cannot assure that this rating will remain at its current level and it is possible that some prospective customers may be reluctant to do business with a company that is not rated by A.M. Best. We have not been reviewed by A.M. Best and do not currently intend to seek a rating from A.M. Best. Unlike Demotech, Inc., A.M. Best may penalize companies that are highly leveraged, including those companies that utilize reinsurance to support premium writings. We do not plan to give up revenues or efficiency of size as a means to qualify for an acceptable A.M. Best rating. Not having an A.M. Best rating may prevent us from expanding our business or limit our access to credit from certain financial institutions, which may in turn limit our ability to compete with large, national insurance companies and certain regional insurance companies.

Our results of operations depend, in part, on the performance of our investment portfolio. We seek to hold a diversified portfolio of investments in accordance with our investment policy and routinely reviewed by our Investment Committee. However, our investments are subject to general economic and market risks as well as risks inherent to particular securities.

Our primary market risk exposures are to changes in interest rates and equity prices. See Part II Item 7A. “Quantitative and Qualitative Disclosures about Market Risk.” A protracted low interest rate environment could place pressure on our net investment income, particularly as it relates to fixed income securities and short-term investments, which, in turn, may adversely affect our operating results. A protracted high interest rate environment could cause the values of our fixed income securities portfolios to decline, with the magnitude of the decline depending on the duration of securities included in our portfolio and the amount by which interest rates increase. Some fixed income securities have call or prepayment options, which create possible reinvestment risk in declining rate environments. Other fixed income securities, such as mortgage-backed and asset-backed securities, carry prepayment risk or, in a rising interest rate environment, may not prepay as quickly as expected.

The value of our investment portfolio is subject to the risk that certain investments may default or become impaired due to deterioration in the financial condition of one or more issuers of the securities we hold, or due to deterioration in the financial condition of an insurer that guarantees an issuer's payments on such investments. Downgrades in the credit ratings of fixed maturities also have a significant negative effect on the market valuation of such securities.

Such factors could reduce our net investment income and result in realized investment losses. Our investment portfolio is subject to increased valuation uncertainties when investment markets are illiquid. The valuation of investments is more subjective when markets are illiquid, thereby increasing the risk that the estimated fair value (i.e., the carrying amount) of the securities we hold in our portfolio does not reflect prices at which actual transactions would occur.

We may also invest in marketable equity securities. These securities are carried on the balance sheet at fair market value and are subject to potential losses and declines in market value.

Risks for all types of securities are managed through the application of our investment policy, which establishes investment parameters that include, but are not limited to, maximum percentages of investment in certain types of securities and minimum levels of credit quality, which we believe are within applicable guidelines established by the NAIC, the NYDFS and the DE Department.

Although we seek to preserve our capital, we cannot be certain that our investment objectives will be achieved, and results may vary substantially over time. In addition, although we seek to employ investment strategies that are not correlated with our insurance and reinsurance exposures, losses in our investment portfolio may occur at the same time as underwriting losses and, therefore, exacerbate the adverse effect of the losses on us.

Specifically negotiated loss limitations or exclusions in our policies may not be enforceable in the manner we intend. As industry practices and legal, judicial, social, and other conditions change, unexpected and unintended issues related to claims and coverage may emerge. For example, many of our policies limit the period during which a customer may bring a claim, which may be shorter than the statutory period under which such claims can be brought against our customers. While these limitations and exclusions help us assess and mitigate our loss exposure, it is possible that a court or regulatory authority could nullify or void a limitation or exclusion or legislation could be enacted modifying or barring the use of such limitations or exclusions. These types of governmental actions could result in higher than anticipated loss and loss adjustment expense, which could have a material adverse effect on our financial condition or results of operations. In addition, court decisions could read policy exclusions narrowly so as to expand coverage, thereby requiring insurers to create and write new exclusions. These issues may adversely affect our business by either broadening coverage beyond our underwriting intent or by increasing the frequency or severity of claims. In some instances, these changes may not become apparent until sometime after we have issued insurance contracts that are affected by the changes. As a result, the full extent of liability under our insurance contracts may not be known for many years after a contract is issued.

Our Giveback works to align our interests with those of our customers, which we believe builds trust, minimizes fraud, and keeps our costs down. If a state, federal authority or foreign jurisdiction finds that the Giveback is a rebate rather than a charitable contribution, or impermissible on other grounds, it could force us to abandon the Giveback in part or entirely, either of which could materially and adversely affect our brand, financial condition and results of operations.

Additionally, we could modify, reduce or eliminate the Giveback at our discretion for a variety of reasons. The Company’s board of directors may determine the amount and distribution of the Giveback by taking into consideration various factors such as the current goodwill and reputation of the causes selected by customers, the amount of funds available for distribution, the reasonableness of such contribution, and general shareholders' interests, such as the proposed amount and distribution of the Giveback against factors like overall shareholder returns, our financial and operating performance, and our social responsibility and the benefits shareholders and their communities receive from proposed contributions.

Further, our commitment to charitable giving through our Giveback program may not align our interests with those of our customers or prospective customers to the extent anticipated. Our commitment to charitable giving may not resonate with our existing customers or may fail to attract new customers. The amount contributed to causes may be viewed as insufficient by existing or new customers. If after weighing any of these factors, the Company's board of directors were to reduce or eliminate the Giveback, our business model would be impacted, which, in turn, could materially and adversely affect our brand, financial condition and results of operations.

As a public benefit corporation (PBC) we are legally required to operate in a responsible and sustainable manner, balancing the financial interests of our stockholders with the best interests of those materially affected by our conduct and the specific public benefits identified in our Amended Charter. To retain our B Corp certification we must meet high standards of verified performance, accountability, and transparency set by B Lab. This unique structure introduces several significant risks:

•Conflict of Fiduciary Duties: Unlike traditional corporations that focus exclusively on maximizing stockholder value, our directors have a fiduciary duty to consider our specific public benefit and other stakeholders. Consequently, we may take actions that we believe serve our public benefit purpose even if they do not maximize financial results or distributions to stockholders. There is no guarantee that conflicts between stockholder interests and our public benefit goals will be resolved in favor of stockholders.

•Reputational and Certification Risks: Our brand relies on the credibility and trust built through our Certified B Corp status. If we lose this certification, or if our publicly reported B Corp score declines, it may create a perception that we are no longer committed to our values, harming our reputation and business. Furthermore, we must publicly disclose a biennial report on our public benefit performance; any failure to provide this report or a negative perception of its contents could damage our status.

•Reduced Attractiveness for Takeovers and Activism: Our PBC status makes us a less attractive target for acquisitions and activist investors. Delaware law requires a two-thirds vote to merge with an entity that does not contain identical public benefit provisions. Additionally, the requirement for directors to consider multiple constituencies may make it easier for the board to reject hostile bids that might otherwise provide a short-term financial yield to stockholders.

•Derivative Litigation Exposure: Stockholders owning at least 2% of our shares may file derivative lawsuits claiming our directors failed to balance stockholder and public benefit interests—a liability that does not exist for traditional corporations. Such litigation could be costly and divert management's attention from executing our business strategy.

•Regulatory Interference with Charitable Contributions: State or federal regulators could restrict or delay our ability to donate residual premiums to customer-selected nonprofits through our Giveback program. Any such interference could erode customer trust, weaken incentives for good customer behavior, and adversely affect demand for our products.

Any failure to achieve our public benefit purpose or maintain our certifications could have a material adverse effect on our reputation, business, results of operations, and stock price.

The trading price of our common stock could be volatile, and you could lose all or part of your investment. The following factors, in addition to other factors described in this "Risk Factors" section and included elsewhere in this document may have a significant impact on the market price of our common stock:

•the occurrence of severe weather conditions and other catastrophes;

•our operating and financial performance, quarterly or annual earnings relative to similar companies;

•publication of research reports or news stories about us, our competitors or our industry, or positive or negative recommendations or withdrawal of research coverage by securities analysts;

•the public's reaction to our press releases, our other public announcements and our filings with the SEC;

•announcements by us or our competitors of acquisitions, business plans or commercial relationships;

•any major change in our board of directors or senior management, including the departure of either of our Co-Founders;

•additional sales of our common stock by us, our directors, executive officers, principal shareholders, or our Co-Founders;

•adverse market reaction to any indebtedness we may incur or securities we may issue in the future;

•short sales, hedging and other derivative transactions in our common stock;

•exposure to capital market risks related to changes in interest rates, realized investment losses, credit spreads, equity prices, foreign exchange rates and performance of insurance- linked investments;

•our creditworthiness, financial condition, performance, and prospects;

•our dividend policy and whether dividends on our common stock have been, and are likely to be, declared and paid from time to time;

•perceptions of the investment opportunity associated with our common stock relative to other investment alternatives;

•regulatory or legal developments;

•changes in general market, economic, and political conditions;

•conditions or trends in our industry, geographies or customers;

•short selling activities

•changes in accounting standards, policies, guidance, interpretations or principles; and

•threatened or actual litigation or government investigations.

In addition, broad market and industry factors may negatively affect the market price of our common stock, regardless of our actual operating performance, and factors beyond our control may cause our stock price to decline rapidly and unexpectedly. In addition, in the past, companies that have experienced volatility in the market price of their stock have been subject to securities class action litigation. We may be the target of this type of litigation in the future. Litigation of this type could result in substantial costs and diversion of management's attention and resources, which could have a material adverse effect on our business, financial condition, results of operations or prospects. Any adverse determination in litigation could also subject us to significant liabilities.

Provisions in our Amended Charter and our Amended Bylaws, as well as provisions of the Delaware General Corporation Law (the "DGCL"), could make it more difficult for a third party to acquire us or increase the cost of acquiring us, even if doing so would benefit our stockholders, including transactions in which stockholders might otherwise receive a premium for their shares. These provisions include:

•our board of directors is classified into three classes of directors with staggered three-year terms and directors are only able to be removed from office for cause;

•nothing in our Amended Charter precludes future issuances without stockholder approval of the authorized but unissued shares of our common stock;

•advance notice procedures apply for stockholders to nominate candidates for election as directors or to bring matters before an annual meeting of stockholders;

•our stockholders will only be able to take action at a meeting of stockholders and not by written consent;

•only our chairman of the board of directors, our chief executive officer, our president (in the absence of the chief executive officer), or a majority of the board of directors are authorized to call a special meeting of stockholders;

•no provision in our Amended Charter or Amended Bylaws provides for cumulative voting, which limits the ability of minority stockholders to elect director candidates;

•directors will only be able to be removed for cause;

•certain amendments to our Amended Charter will require the approval of two-thirds of the then outstanding voting power of our capital stock;

•our Amended Bylaws will provide that the affirmative vote of two-thirds of the then-outstanding voting power of our capital stock, voting as a single class, is required for stockholders to amend or adopt any provision of our bylaws;

•our Amended Charter authorizes undesignated preferred stock, the terms of which may be established and shares of which may be issued, without the approval of the holders of our capital stock; and

•certain litigation against us can only be brought in Delaware.

These anti-takeover defenses could discourage, delay or prevent a transaction involving a change in control of our Company. These provisions could also discourage proxy contests and make it more difficult for you and other stockholders to elect directors of your choosing and cause us to take corporate actions other than those you desire.

Under applicable state insurance laws and regulations, no person may acquire control of a domestic insurer until written approval is obtained from the state insurance commissioner following a public hearing on the proposed acquisition. Such approval would be contingent upon the state insurance commissioner's consideration of a number of factors including, among others, the financial strength of the proposed acquiror, the acquiror's plans for the future operations of the domestic insurer and any anti- competitive results that may arise from the consummation of the acquisition of control. LIC is domiciled in New York and MIC is domiciled in Delaware. Per the applicable laws and regulations of New York and Delaware, respectively, generally no person may acquire control of any insurer, whether by purchase of its securities or otherwise, unless it gives prior notice to the insurer and has received prior approval from the superintendent or Commissioner of Financial Services. Under New York and Delaware insurance law, an entity is presumed to have control of an insurance company if it owns, directly or indirectly, 10% or more of the voting stock of that insurance company or its parent company. These requirements may discourage potential acquisition proposals and may delay, deter, or prevent a change of control of Lemonade, Inc., including through transactions that some or all of the stockholders might consider to be desirable.

Our Amended Charter provides that the Court of Chancery of the State of Delaware will be the sole and exclusive forum for (i) any derivative action or proceeding brought on our behalf, (ii) any action asserting a claim of breach of a fiduciary duty owed to us or our stockholders by any of our directors, officers, employees or agents, (iii) any action asserting a claim against us arising under the DGCL or (iv) any action asserting a claim against us that is governed by the internal affairs doctrine; provided that, the exclusive forum provision will not apply to suits brought to enforce any liability or duty created by the Securities Act or the Exchange Act, or to any claim for which the federal courts have exclusive jurisdiction. By becoming a stockholder in the Company, you will be deemed to have notice of and have consented to the provisions of our Amended Charter related to choice of forum. The choice of forum provision in our Amended Charter may limit our stockholders' ability to obtain a favorable judicial forum for disputes with us. Additionally, the enforceability of choice of forum provisions in other companies’ governing documents has been challenged in legal proceedings, and it is possible that, in connection with any applicable action brought against us, a court could find the choice of forum provisions contained in our Amended

Charter to be inapplicable or unenforceable in such action. If so, we may incur additional costs associated with resolving such action in other jurisdictions, which could harm our business, results of operations, and financial condition.

We are subject to the rules and regulations established from time to time by the SEC and the New York Stock Exchange (“NYSE”). These rules and regulations require, among other things, that we establish and periodically evaluate procedures with respect to our internal control over financial reporting. Such reporting obligations place a considerable strain on our financial and management systems, processes and controls, as well as our personnel.

In addition, we are required to document and test our internal controls over financial reporting pursuant to Section 404 of the Sarbanes-Oxley Act (“SOX”) so that our management can certify as to the effectiveness of our control over financial reporting by the time our annual report is filed with the SEC. Section 404(b) also requires our independent registered public accounting firm to issue an annual report that addresses the effectiveness of our internal control over financial reporting. If we identify material weaknesses in our internal control over financial reporting or if we are unable to comply in a timely manner with the requirements of Section 404 of the SOX, we may be unable to accurately report our financial results, or report them within the timeframes required by the SEC. We also could become subject to sanctions or investigations by the SEC or other regulatory authorities. In addition, if we are unable to assert that our internal control over financial reporting is effective, or if our independent registered public accounting firm is unable to express an opinion as to the effectiveness of our internal control over financial reporting, when required, investors may lose confidence in the accuracy and completeness of our financial reports, we may face restricted access to the capital markets and our stock price may be adversely affected.

We are a holding company that transacts a majority of our business through operating subsidiaries. Our ability to meet our operating and financing cash needs depends on the surplus and earnings of our subsidiaries, and upon the ability of our insurance subsidiaries to pay dividends to us.

Payments of dividends by our insurance subsidiaries are restricted by state insurance laws, including laws establishing minimum solvency and liquidity thresholds. The limitations are based on income and surplus determined in accordance with statutory accounting principles, not GAAP. In addition, our insurance subsidiaries could be subject to contractual restrictions in the future, including those imposed by indebtedness we may incur in the future. Our insurance subsidiaries may also face competitive pressures in the future to maintain insurance financial stability or strength ratings. These restrictions and other regulatory requirements would affect the ability of our insurance subsidiaries to make dividend payments and we may not receive dividends in the amounts necessary to meet our obligations. See "Business - Regulation of Our Business — Restrictions on Paying Dividends."

We do not currently expect to pay any cash dividends on our common stock for the foreseeable future. Instead, we intend to retain future earnings, if any, for the future operation and expansion of our business. Any determination to pay dividends in the future will be at the discretion of our board of directors and will depend on our results of operations (including our ability to generate cash flow in excess of expenses and our expected or actual net income), liquidity, cash requirements, financial condition, retained earnings and collateral and capital requirements, general business conditions, contractual restrictions, legal, tax and regulatory limitations, the effect of a dividend or dividends upon our financial strength ratings, and other factors that our board of directors deems relevant. See "Dividends."

Because we are a holding company and all of our business is conducted through our subsidiaries, dividends, distributions and other payments from, and cash generated by, our subsidiaries will be our principal sources of cash to fund operations and pay dividends. Accordingly, our ability to pay dividends to our stockholders is dependent on the earnings and distributions of funds from our subsidiaries. Our ability to pay dividends may also be restricted by the terms of any future credit agreement or any of our future debt or preferred equity securities or our subsidiaries. Accordingly, if you purchase shares of our common stock, realization of a gain on your investment will depend on the appreciation of the price of shares of our common stock, which may never occur. Investors seeking cash dividends in the foreseeable future should not purchase our common stock.

We cannot predict the extent to which investor interest in us will sustain a trading market on the NYSE or how active and liquid that market may remain. If an active and liquid trading market is not sustained, you may have difficulty selling any of our common stock that you purchase at a price above the price you purchase it or at all. The failure of an active and liquid trading market to continue would likely have a material adverse effect on the value of our common stock. The market price of our common stock may decline below the public offering price, and you may not be able to sell your shares of our common stock at or above the price you paid or at all. An inactive market may also impair our ability to raise capital to continue to fund operations by selling shares and may impair our ability to acquire other companies or technologies by using our shares as consideration.

The trading market for our common stock will be influenced by the research and reports that industry or securities analysts may publish about us, our business, our markets, or our competitors. Analysts may not continue to cover us or provide favorable coverage. If any of the analysts who may cover us adversely change their recommendation regarding our stock, or provide more favorable relative recommendations about our competitors, our stock price could materially decline. If any analyst who may cover us were to cease coverage of the Company or fail to regularly publish reports on us, we could lose visibility in the financial markets, which in turn could cause our stock price or trading volume to materially decline.

None.

        

We have developed and implemented a cybersecurity risk management program intended to protect the confidentiality, integrity, and availability of our critical systems and information.

Our cybersecurity risk management program is informed by best practice approaches relevant to the technologies we use, the environments in which our services are designed and deployed, our business needs, and relevant regulatory requirements. This does not imply that we meet any particular technical standards, specifications, or requirements, only that we use the various standards and frameworks as guides to help us identify, assess, and manage cybersecurity risks relevant to our business.

Our cybersecurity risk management program is integrated into our overall enterprise risk management program, and shares common approaches, reporting channels, and governance processes that apply the enterprise risk management program to other legal, compliance, strategic, operational, and financial risk areas.

Our cybersecurity risk management program includes, but is not limited to the following:

•Risk assessments designed to help identify risks from cybersecurity threats to our critical systems and information;

•A security team principally responsible for managing (1) our cybersecurity risk assessment processes, (2) our security controls, and (3) our response to cybersecurity incidents;

•The use of external service providers, where appropriate, to assess, test or otherwise assist with aspects of our security processes;

•Security tools deployed in the IT environment for protection against and monitoring of suspicious events;

•Security awareness training of our employees, including incident response personnel, and senior management;

•A cybersecurity incident response plan that includes procedures for responding to cybersecurity incidents; and

•A third-party risk management process for key service providers based on our assessment of their criticality to our operations and respective risk profile.

We have not identified known cybersecurity threats to date that could have materially affected or are reasonably likely to materially affect us, including our operations, business strategy, results of operations, or financial condition. We face certain ongoing risks from cybersecurity threats such as loss or theft of data, disruptive attacks from financially motivated bad actors, and third party supply chain issues that, if realized, are reasonably likely to materially affect us, including our operations, business strategy, results of operations, or financial condition. See “Risk Factors – Risks Relating to Our Business.”

Our Board considers cybersecurity risk as a critical part of its risk oversight function and has delegated to the Audit Committee oversight of cybersecurity risks, including management’s implementation of our cybersecurity risk management.

The Audit Committee periodically receives reports on our cybersecurity risks from our Chief Information Security Officer (“CISO”) or his designee. In addition, management updates the Audit Committee, where it deems appropriate, regarding cybersecurity incidents it considers significant or potentially significant.

The Audit Committee regularly reports its activities, including those related to cybersecurity, to the full Board. The full Board also receives briefings from management on our cyber risk management. As part of the Board’s continuing education on topics that impact public companies, Board members receive presentations on cybersecurity topics from our CISO or his designee.

The management team delegates responsibility for assessing and managing our cybersecurity risks to the CISO. The CISO has primary responsibility for our overall cybersecurity risk management and supervises both our internal cybersecurity personnel and any external cybersecurity consultants. The CISO has over two decades of security work that includes work for large global enterprises, managing global security teams, and establishing and running security programs for both conventional and high-tech companies, including publicly traded and regulated companies. The CISO reports to an internal security committee periodically regarding current security posture, risk, and trending security incidents and threats relevant to the Company. The security committee comprises key management personnel, department heads, and business unit leaders.

Our management team takes steps to stay informed about and monitor efforts to prevent, detect, mitigate, and remediate cybersecurity risks and incidents through various means, which includes managing a security team and security tools, and as appropriate may include briefings from internal security personnel threat intelligence and other information obtained from governmental, public or private sources, including external consultants engaged by us; and alerts and reports produced by security tools deployed in our IT environment.

The Company does not own any real property. Our principal office is located at 5 Crosby Street, 3rd Floor, New York, New York 10013 under a lease agreement that terminates in February 2029. This office space is used for corporate functions and business operations.

The Company leases additional office space in Tel Aviv and Amsterdam, to support our operations in Israel, and Europe. See “Note 21 - Leases”. We believe that our facilities are sufficient to meet our current needs and that suitable additional space will be available as and when needed.

The Company is occasionally a party to routine claims or litigation incidental to its business. See “Note 20 - Commitments and Contingencies” in our consolidated financial statements included elsewhere in this Annual Report. The Company does not believe that it is a party to any pending legal proceeding that is likely to have a material adverse effect on its business, financial condition or results of operations.

Not applicable.

The following table sets forth information regarding our executive officers and directors as of the date of this Annual Report.

(1)        Member of the Audit Committee

(2)        Member of the Compensation Committee

(3)        Member of the Nominating and Corporate Governance Committee

    

The following is a brief biography of each of our executive officers and directors:

Daniel Schreiber has served as our Co-Founder, Chief Executive Officer, and Chairman of our board of directors since our founding in June 2015. Prior to co-founding Lemonade in 2015, Mr. Schreiber served as President and a member of the board of directors of Powermat Technologies Ltd., a wireless charging solutions and technology company, from 2011 to 2015. From 2003 to 2011, he served as Senior Vice President of Marketing and Vice President of Marketing and Business Development at SanDisk and M-Systems (which was acquired by SanDisk in 2006), respectively. In 1997, Mr. Schreiber co-founded and acted as the Chief Executive Officer of Alchemedia Inc., an internet security software company acquired by Finjan Software in 2002. Prior to that, Mr. Schreiber practiced corporate commercial law at Herzog, Fox & Neeman, and was a member of the Israeli Bar Association. He holds a Bachelor of Laws with First Class Honors from King’s College London.

Shai Wininger has served in various roles, including as our Co-Founder, Co-Chief Executive Officer, Secretary, Treasurer, and Chief Technology Officer, since our founding in June 2015. Mr. Wininger has served as our President since January 1, 2024, and is a member of our board of directors since June 2015. Prior to co-founding Lemonade in 2015, Mr. Wininger founded Fiverr Ltd. in 2009, and as the Chief Technology Officer, managed the engineering, design, and product departments. Prior to 2010, Mr. Wininger served in senior management capacities for companies including: from 2005 to 2010, Mobideo Aerospace, an industrial grade analytics and control platform; from 2003 to 2005, Handsmart Software, a mobile licensing platform for content driven, mobile apps; and from 1999 to 2003, Trimus Inc., a virtual reality web browser. Mr. Wininger also served as a resident faculty member of Computer Graphics at The Neri Bloomfield Academy of Design and Education from 2002 to 2007 in Haifa, Israel.

Adina Eckstein has served as the Company’s Chief Operating Officer since July 2021. Prior to becoming our Chief Operating Officer, Ms. Eckstein served as our Vice President of Operations since November 2020. Prior to joining the Company in 2019, Ms. Eckstein served as Chief Operating Officer of HSBC, where she helped one of the world’s largest financial institutions with the digitization of its business. Prior to that, from 2014 to 2016, Ms. Eckstein served as Vice President of Programme and Portfolio at BBC Worldwide, where she led the development and operations of all consumer digital technology. She holds a Bachelor of Arts in Economics in Hebrew University and a Master of Business Administration from Tel Aviv University.

Tim Bixby has served as our Chief Financial Officer since June 2017. From February 2021 through October 2025, he served as a director and as chair of the audit committee of the board of directors of Rent the Runway, a leading e-commerce fashion rental and resale business. Prior to joining Lemonade, Mr. Bixby served as Chief Financial Officer of Shutterstock, Inc., a digital content licensing marketplace, from 2011 to 2015. From 1999 to 2011 he served as the Chief Financial Officer, President, and a member of the board of directors of LivePerson, Inc., a provider of cloud mobile and online business messaging solutions. He holds a Bachelor of Arts in Mathematics from Dartmouth College and a Master of Business Administration from Harvard Business School.

John Peters has served as our Chief Insurance Officer since September 2016. Prior to joining Lemonade, he served as the Executive Vice President of Commercial Insurance Operations and the Chief Underwriting and Product Officer, Regional Companies Group for Liberty Mutual Insurance from 2011 to 2016. Mr. Peters also spent ten years with McKinsey & Company’s global property-casualty insurance practice, serving in various roles including partner. He holds a Bachelor of Arts in Mathematics and German from Bowdoin College and is a former fellow of the Casualty Actuarial Society.

Maya Prosor is a founding team member of Lemonade and has served as our Chief Business Officer since July 2022. Prior to becoming our Chief Business Officer, Ms. Prosor served in different roles at Lemonade, including Homeowners company lead from July 2020 to July 2022, and VP business development from August 2015 to July 2020. Prior to joining Lemonade in 2015, Ms. Prosor was the AVP of market development for the joint venture of Duracell and Powermat Technologies Ltd. a wireless charging solutions and technology company, from 2010 to 2015. She holds a Bachelor’s Art from the Reichman University in Business Administration and Entrepreneurship and is a graduate of the Zell Entrepreneurship Program.

Michael Eisenberg has served as a member of our board of directors since July 2015. Mr. Eisenberg is a Partner at Aleph, an early stage venture capital fund that invests in Israeli entrepreneurs, which he joined in July 2013. In addition to his role on our board of directors, Mr. Eisenberg serves as a member of the board of several private companies. He holds a Bachelor of Arts in Political Science from Yeshiva University.

Dr. Samer Haj-Yehia has served as a member of our board of directors since November 2023. Dr. Haj-Yehia brings extensive executive and board experience at various conglomerates across multiple industries in Israel and the US. Until October 2023, he was the Group Executive Chairman of Bank Leumi, Israel’s largest and oldest bank. Under his leadership since 2019, Leumi became the largest and most efficient bank in Israel, grew its income and profitability, and underwent technological transformation and innovation. While in the US, Dr. Haj-Yehia practiced investment management, trading, and fintech innovation at leading financial institutions, including at Fidelity. He also served as a member of public and government committees, teaches finance and fintech at Reichman University, and is a guest speaker at international conferences. Dr. Haj-Yehia holds a Ph.D. in economics from MIT, and an MBA (summa cum laude), LLB, MA (magna cum laude) in economics, and BA (magna cum laude) in accounting, all from Hebrew University. He is a CFA charterholder.

Prashant Ratanchandani has served as a member of our board of directors since October 2025. Mr. Ratanchandani is the VP of Engineering for AI Products at Meta, supporting the engineering teams responsible for building Meta’s Generative AI products. He has held several leadership roles at Meta, building and scaling technical organizations responsible for core experiences across Meta products. Prior to Meta, he held leadership roles at Microsoft, with a focus on the fundamentals of the Windows operating system. He holds a Bachelor of Technology in Computer Science from the Indian Institute of Technology, Kharagpur where he received the B.C Roy Gold Medal, and also holds a Master of Science degree from the University of Illinois at Urbana Champaign.

Debra Schwartz has served as a member of our board of directors since November 2023. Ms. Schwartz is a seasoned financial leader skilled at enabling companies to innovate, grow and scale. She is currently the Chief Financial Officer at Goldbelly, Inc., the leading curated marketplace for American food culture. Prior to Goldbelly, She served as CFO at H1, a leading healthcare data technology company whose mission is to connect the world to the right doctors. She previously served as CFO at Cameo, the celebrity video shoutout pioneer, and at Bustle Digital Group, the digital media provider. Ms. Schwartz spent more than a decade as an equity analyst with Goldman Sachs and Credit Suisse, and holds an MBA from Harvard University, and a BA/BS from the University of Pennsylvania.

Geoff Seeley has served as a member of our board of directors since October 2025. Mr. Seeley is the Chief Marketing Officer of PayPal Holdings, Inc., a role he has held since February 2024, where he leads global marketing for PayPal and Venmo. Previously, Mr. Seeley served as Global Chief Marketing and Communications Officer at Afterpay, where he helped scale both consumer and merchant adoption —culminating in the $29 billion sale to Block, Inc. (formerly Square). Previously, he led global marketing at Airbnb, driving brand equity resulting in guest and host growth. Mr. Seeley previously held senior roles at Unilever and Pearson over a 30+ year career spanning brand strategy and performance marketing, large-scale rebrands, and modernization of marketing technology and analytics. He is a frequent speaker at industry forums. Mr. Seeley holds a B.Sc. from University College London.

Maria Angelidis-Smith has served as a member of our board of directors since October 2024. Ms. Angelidis-Smith is the Chief Product Officer of Reddit, Inc. Prior to Reddit, she served as Chief Product and Technology Officer of Personio, Europe’s leading HR software provider empowering small and mid-sized organizations and Vice President of Product and General Manager at Meta, leading and scaling the monetization of the Facebook App as well as billion+ user products such as Facebook Groups, Events and Profile. She previously held leadership roles with several companies, including Intuit and The Boston Consulting Group, focused primarily on product development, growth strategies, and marketing. She holds a BBA in Economics, Operations and Marketing from Athens University of Economics and Business, and an MBA from University of Michigan - Stephen M. Ross School of Business, where she was a Fulbright Scholar.

The Company’s common stock is listed and traded on the New York Stock Exchange under the trading symbol “LMND”.

As of February 24, 2026, there were 134 holders of record of the Company’s common stock.

We have never declared or paid any cash dividends on our capital stock. We currently intend to retain any future earnings and do not expect to pay any dividends in the foreseeable future. Any future determination to declare cash dividends will be made at the discretion of our board of directors, subject to applicable laws, and will depend on a number of factors, including our financial condition, results of operations, capital requirements, contractual restrictions, general business conditions, and other factors that our board of directors may deem relevant.

The following performance graph compares the cumulative total shareholder return of an investment in our common shares since July 2, 2020 (first day of trading) through December 31, 2025 to the cumulative total return of Nasdaq Composite Stock Index (“Nasdaq Index”) and the Nasdaq Insurance Index (“Nasdaq Insurance Index”). The graph assumes that $100 was invested on July 2, 2020 and the reinvestment of dividends, if any. The share price performance presented below is not necessarily indicative of future results.

The foregoing performance graph and data shall not be deemed “filed” as part of this Annual Report for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that section and should not be deemed incorporated by reference into any other filing of the Company under the Securities Act of 1933, as amended, or the Securities Exchange Act of 1934, except to the extent the Company specifically incorporates it by reference into such filing.

There have been no recent sales of unregistered securities.

None.

Item 6.    [Reserved]

The following discussion and analysis of our financial condition and results of operations should be read in conjunction with our consolidated financial statements, the accompanying notes and other information included elsewhere in this Annual Report. This discussion and analysis below includes forward-looking statements that are subject to risks, uncertainties and other factors described in the “Risk Factors” section that could cause actual results to differ materially from such forward-looking statements. Additionally, our historical results are not necessarily indicative of the results that may be expected for any period in the future. A discussion of the year ended December 31, 2024 compared to the year ended December 31, 2023 has been reported previously under “Management’s Discussion and Analysis of Financial Condition and Results of Operations” in our Annual Report on Form 10-K for the year ended December 31, 2024 filed with the SEC on February 26, 2025 (the “2024 Annual Report”).

Lemonade is rebuilding insurance from the ground up on a digital substrate and an innovative business model. By leveraging technology, data, artificial intelligence, contemporary design, and social impact, we believe we are making insurance more delightful, more affordable, and more precise. To that end, we have built a vertically-integrated company with wholly-owned insurance carriers in the United States and Europe, including the UK and the full technology stack to power them.

A brief chat with our bot, AI Maya, is all it takes to get covered with renters, homeowners, pet, car or life insurance, and we expect to offer a similar experience for other insurance products over time. Claims are filed by chatting with another bot, AI Jim, who pays claims in as little as two seconds. This breezy experience belies the extraordinary technology that enables it: a state-of-the-art platform that spans marketing to underwriting, customer care to claims processing, finance to regulation. Our architecture melds artificial intelligence with the human kind, and learns from the prodigious data it generates to become even better at delighting customers and evaluating risks.

In addition to digitizing insurance end-to-end, we also reimagined the underlying business model to minimize volatility while maximizing trust and social impact. To lessen the volatility inherent in an industry directly impacted by the weather, we utilize several forms of reinsurance, with the goal of dampening the impact on our gross margin. The result is that excess claims are generally offloaded to reinsurers, while excess premiums can be donated to nonprofits selected by our customers as part of our "Giveback". These two ballasts, reinsurance and Giveback, reduce volatility, while creating an aligned, trustful, and values-rich relationship with our customers. See “Business - Our Business Model” and “Business - Our Product Offerings - Giveback Feature.”

On June 28, 2023, we entered into a Customer Investment Agreement (the “Agreement”), with GC Customer Value Arranger, LLC (a General Catalyst company) ("GC") under which GC agreed to provide up to $150 million of financing for our sales and marketing growth efforts through December 31, 2024. Under the Agreement, subject to certain terms and conditions specified therein, at the start of each growth period, an Investment Amount of up to 80% of our growth spend (the "Investment Amount") will be advanced by GC. During each growth period, we repay each Investment Amount including a 16% rate of return based upon an agreed schedule. Once fully repaid, we retain all future reference income related to each respective Investment Amount.

The Agreement has been amended and restated on several occasions to extend the commitment period and increase the financing agreement. On January 8, 2024, the Agreement was amended and restated to provide up to an additional $140 million of financing December 31, 2025. On February 3, 2025, the Agreement was further amended to provide up to an additional $200 million of financing from January 1, 2026 through December 31, 2026 for our sales and marketing growth efforts. In addition, the Agreement was amended in April 2024, June 2024 and December 2025 to clarify certain provisions with no changes to material terms. The Agreement, as amended and restated (the “Amended and Restated Agreement”) contains standard customary representations, warranties and covenants by the parties, and will continue in effect unless terminated by any party pursuant to its terms.

As of December 31, 2025, we had $158.1 million of outstanding borrowings under the Amended and Restated Agreement. We incurred interest expense of $17.3 million for the year ended December 31, 2025.

Our financial condition and results of operations have been, and will continue to be, affected by a number of factors, including the following:

Seasonal patterns can impact both our rate of customer acquisition and the incurrence of claims and losses.

Based on historical experience, existing and potential customers move more frequently in the third quarter, compared to the rest of the calendar year. As a result, we may see greater demand for new or expanded insurance coverage, and increased online engagement resulting in proportionately more growth during the third quarter. We expect that as we grow our customers, expand geographically and launch new products, the impact of seasonal variability on our rate of growth may decrease.

Additionally, seasonal weather patterns impact the level and amount of claims we receive. These patterns include hurricanes, wildfires, and coastal storms in the fall, cold weather patterns and changing home heating needs in the winter, and tornados and hailstorms in the spring and summer. The mix of geographic exposure and products within our customer base impacts our exposure to these weather patterns. For additional information, see "Risk Factors — Risks Relating to our Industry — Severe weather events and other catastrophes, including the effects of climate change and global pandemics, are inherently unpredictable and may have a material adverse effect on our financial results and financial condition."

Changing U.S. and global conditions may impact our business. Evolving U.S. trade policy, including tariffs imposed on imported goods in 2025, could affect our claims costs. In February 2026, the United States Supreme Court ruled that the use of the International Emergency Economic Powers Act ("IEEPA") to impose tariffs was not authorized by Congress, invalidating a significant portion of tariffs that had been in effect since April 2025. While the ruling struck down the IEEPA-based tariffs, it does not prevent the administration from imposing tariffs using other legal authorities. Following the ruling, the administration invoked alternative statutory authorities imposing a global tariff, and the administration has indicated its intention to continue to pursue alternative statutory mechanisms to reinstate or impose new tariffs. Tariffs on building materials may increase home repair costs, tariffs on automotive parts may increase vehicle repair and replacement costs, and tariffs on consumer goods may increase the cost of replacing covered personal property. To the extent tariff-driven cost increases are sustained, we may seek premium rate adjustments, subject to regulatory approval in applicable states; however, there may be a lag between when we experience increased claims costs and when we are able to implement corresponding rate increases, which could negatively impact our loss ratios in the interim. More broadly, inflation, whether driven by tariffs, supply chain disruptions, labor market conditions, or other factors, if any, has impacted and could continue to our claims costs, product pricing and investment yield, among other impacts. Capital market volatility may also affect our investment portfolio and access to capital. The actual effects of these macroeconomic factors on our results remains to be unknown and cannot be estimated with precision.

We conduct certain of our operations in Israel and therefore our results may be adversely affected by political, economic and military instability and conflict in Israel and the surrounding region. There is still uncertainty regarding the extent to which the war and its broader macroeconomic implications will impact our operations in Israel. We will continue to evaluate the extent to which this may impact our business, financial condition, or results of operations. These and other uncertainties could result in changes to our current expectations. For additional information, see “Risk Factors - Risks Relating to our Business - We conduct certain of our operations in Israel and therefore our results may be adversely affected by political, economic and military instability in Israel and the surrounding region.”

We obtain reinsurance to help manage our exposure to property and casualty insurance risks. Although our reinsurance counterparties are liable to us according to the terms of the reinsurance policies, we remain primarily liable to our policyholders as the direct insurers on all risks reinsured, see "Risk Factors - Risks Relating to Our Business” and “Risks Relating to Our Industry.” As a result, reinsurance does not eliminate the obligation of our insurance subsidiaries to pay all claims, and we are subject to the risk that one or more of our reinsurers will be unable or unwilling to honor its obligations, that the reinsurers will not pay in a timely fashion, or that our losses are so large that they exceed the limits inherent in our reinsurance contracts, each of which could have a material effect on our results of operations and financial condition. Furthermore, reinsurance may be unavailable at current levels and prices, which may limit our ability to write new business.

We maintain proportional reinsurance contracts which cover all of the Company's products and geographies, and transfer, or “cede,” a specified percentage of the premium to reinsurers. We also manage the remaining percentage of the business with alternative forms of reinsurance through non-proportional reinsurance contracts.

We agreed to the terms of our reinsurance program effective July 1, 2024 through June 30, 2025 which included Whole Account Quota Share Reinsurance Contracts by and among the Company, LIC, MIC and Lemonade Insurance N.V. ("LINV"), and each of Hannover Ruck SE ("Hannover"), MAPFRE Re Compania De Reaseguros S.A. ("MAPFRE"), and Swiss Reinsurance America Corporation (collectively referred to as “Reinsurers”) ("Reinsurance Program"). Under the Reinsurance Program, which covers all products and geographies, the Company transfers, or "cedes," approximately 55% of premium to the Reinsurers. In exchange, these Reinsurers pay us a ceding commission on all premiums ceded to the Reinsurers, in addition to funding the corresponding claims, subject to certain limitations, including but not limited to, the exclusion of hurricane losses, and a limit of $10,000,000 per occurrence for non-hurricane catastrophe losses. The Per Risk Cap across the contracts is $750,000. Additionally, these contracts are subject to loss ratio caps and variable ceding commission, which align our interests with those of our Reinsurers and is settled primarily on a funds withheld basis. We renewed the Reinsurance Program with Hannover and MAPFRE effective July 1, 2025 and will expire on June 30, 2026, with a reduced effective cession rate of 20% and with other terms similar to the contracts that expired on June 30, 2025.

LIC and MIC entered into a Property Per Risk Excess of Loss Reinsurance Contract with a panel of reinsurance companies (the "PPR Contract") which was effective July 1, 2024 and expired on June 30, 2025. Under the PPR Contract, claims in excess of $750,000 were 100% ceded up to a maximum recovery of $2,250,000, subject to certain limitations. The PPR Contract was renewed at similar terms effective July 1, 2025 and will expire on June 30, 2026.

LIC entered into an Automatic Facultative PPR Contract with Arch Reinsurance, which was effective July 1, 2023 and expired on June 30, 2024. The Automatic Facultative PPR Contract, in which claims in excess of $3,000,000 were 100% ceded with a potential recovery of at least $10,000,000, subject to certain limitations, which expired on June 30, 2024, and was not renewed.

We also entered into an Excess of Loss Reinsurance Contract (the "XOL reinsurance contract") through a captive in Bermuda in which we have a variable interest. This XOL reinsurance contract primarily covers catastrophe risk on property and car business underwritten by LIC and MIC over the initial $50,000,000 limit for each loss occurrence, and further subject to a limit of $80,000,000 for each loss occurrence and in aggregate. This XOL reinsurance contract effective July 1, 2024 expired on June 30, 2025, and was renewed at similar terms effective July 1, 2025 and expiring on June 30, 2026.

We are also exposed to some risks on property, auto and pet insurance underwritten by LIC and MIC ceded through Quota Share Reinsurance Contracts (the "QS reinsurance contracts") which is retained in an offshore captive subsidiary, Lemonade Re SPC in the Cayman Islands. The MIC QS reinsurance contract which became effective July 1, 2023 was terminated and the parties agreed to a new QS reinsurance contract effective July 1, 2025 on the same terms except for the increase in cession rate to 35% and ceding commission rate effective July 1, 2025. The new MIC QS reinsurance contract will remain effective for an indefinite period until terminated by either party. The LIC QS reinsurance contract became effective on July 1, 2025 and will expire on June 30, 2026.

Through our captives, we are exposed to the risk of natural catastrophe events and other covered risks under the reinsurance agreements from assumed risks from policies underwritten by both LIC and MIC.

Gross written premium is the amount received, or to be received, for insurance policies written by us during a specific period of time without reduction for premiums ceded to reinsurers. Gross written premium includes direct and assumed premium. The volume of our gross written premium in any given period is generally influenced by new business submissions, binding of new business submissions into policies, renewals of existing policies, and average size and premium rate of bound policies.

Ceded written premium is the amount of gross written premium ceded to reinsurers. We enter into reinsurance contracts to limit our exposure to potential losses as well as to provide additional capacity for growth. Ceded written premium is earned over the reinsurance contract period in proportion to the period of risk covered. The volume of our ceded written premium is impacted by the level of our gross written premium and any decision we make to increase or decrease in reinsurance limits, retention levels and co-participation. Our ceded written premium can also be impacted significantly in certain periods due to changes in reinsurance agreements. In periods where we start or stop ceding a large volume of our premium, ceded written premium may increase or decrease significantly compared to prior periods and these fluctuations may not be indicative of future trends.

Gross earned premium represents the earned portion of our gross written premium. Gross earned premium includes direct and assumed premium. Our insurance policies generally have a term of one year and premium is earned pro rata over the term of the policy. In addition, we also include earned premiums from the pay-per-mile car insurance policies which are written for six-month terms. Premium for the policy provides a base rate per month for the entire policy term upon binding of the policy plus a per-mile rate multiplied by the miles driven each day (based on data from the telematics device, subject to a daily maximum).

Ceded earned premium is the amount of gross earned premium ceded to reinsurers.

Net earned premium represents the earned portion of our gross written premium, less the earned portion that is ceded to third-party reinsurers under our reinsurance agreements. Premium is earned pro rata over the term of the policy, which is generally one year. Net earned premiums from the pay-per-mile car insurance policies is earned over the term of the policy which is written for six-month terms.

Ceding commission income is commission we receive based on the premium ceded to third-party reinsurers to reimburse us for acquisition and underwriting expenses. We earn commissions on reinsurance premium ceded in a manner consistent with the recognition of the earned premium on the underlying insurance policies, on a pro-rata basis over the terms of the policies reinsured. The portion of ceding commission income which represents reimbursement of successful acquisition costs related to the underlying policies is recorded as an offset to other insurance expense.

Net investment income represents interest earned from fixed maturity securities, short term and other investments, net of investment fees paid to the Company’s investment manager. Our cash and invested assets are primarily comprised of fixed maturity securities, and may also include cash and cash equivalents, equity securities, and short-term investments. The principal factors that influence net investment income are the size of our investment portfolio and the yield on that portfolio. As measured by amortized cost (which excludes changes in fair value, such as changes in interest rates), the size of our investment portfolio is mainly a function of our invested equity capital along with premium we receive from our customers less payments on customer claims. Over time, we expect that net investment income will represent a more meaningful component of our results of operations.

Commission income consists of commissions earned for policies placed with third-party insurance companies where we have no exposure to the insured risk. Such commission is recognized on the effective date of the associated policy which is when the performance obligation is completed. Other income primarily consists of fees collected from policyholders relating to installment premiums. These fees are recognized at the time each policy installment is billed. Other income also includes net realized gains or losses from sale of investments and sublease income.

Loss and loss adjustment expense (“LAE”), net represent the costs incurred for losses net of amounts ceded to reinsurers. We enter into reinsurance contracts to limit our exposure to potential losses as well as to provide additional capacity for growth. These expenses are a function of the size and term of the insurance policies we write and the loss experience associated with the underlying risks. Loss and LAE are based on an actuarial analysis of the estimated losses, including losses incurred during the period and changes in estimates from prior periods. Loss and LAE may be paid out over a period of years. Certain policies we write are subject to catastrophe losses. Catastrophe losses are losses resulting from events involving claims and policyholders, including earthquakes, hurricanes, floods, storms, terrorist acts or other aggregating events that are designated by internationally recognized organizations, such as Property Claims Services, that track and report on insured losses resulting from catastrophic events.

Other insurance expense consists primarily of amortization of commissions and premium taxes incurred on the successful acquisition of business written on a direct basis, and credit card processing fees not charged to our customers. Other insurance expense also includes employee compensation, including stock-based compensation and benefits, of our underwriting teams as well as allocated occupancy costs and related overhead based on headcount. Other insurance expense is offset by the portion of ceding commission income which represents reimbursement of successful acquisition costs related to the underlying policies.

Sales and marketing includes third-party marketing, advertising, branding, public relations and sales expenses. Sales and marketing also includes associated employee compensation, including employee and non employee stock-based compensation and benefits, as well as allocated occupancy costs and related overhead based on headcount. Sales and marketing costs are expensed as incurred.

We plan to continue to invest in sales and marketing to attract and acquire new customers and increase our brand awareness. We expect that, in the long-term, our sales and marketing costs will decrease as a percentage of revenue as we continue to drive customer acquisition efficiencies and as the proportion of renewals to our total business increases.

Technology development consists of employee compensation, including stock-based compensation and benefits, and expenses related to vendors engaged in product management, design, development and testing of our websites and products. Technology development also includes allocated occupancy costs and related overhead based on headcount. We expense technology development costs as incurred, except for costs that are capitalized related to internal-use software development projects and subsequently depreciated over the expected useful life of the developed software.

We expect to continue to incur product technology development costs, a portion of which will be capitalized, to continue to grow in the foreseeable future as we identify opportunities to invest in the development of new products and internal tools and enhancement of our existing products and technologies that we believe will drive the long-term profitability of the business.

General and administrative includes employee compensation, including stock-based compensation and benefits for executive, finance, accounting, legal, business operations, and other administrative personnel. In addition, general and administrative includes outside professional services, non-income based taxes, insurance, charitable donations, bad debt expense and allocated occupancy costs and related overhead based on headcount. Depreciation and amortization expense, interest expense on borrowings under the financing agreement, and non-recurring items, if any are also recorded as a component of general and administrative.

We expect to continue to incur incremental general and administrative costs to support our global operational growth and enhancements to support our reporting and planning functions.

We have incurred and expect to continue to incur significant additional general and administrative expense as a result of operating as a public company, including expenses related to compliance with the rules and regulations of the SEC and the listing standards of the NYSE, additional corporate, director and officer insurance expenses, greater investor relations expenses and increased legal, audit and consulting fees.

Our provision for income taxes consists primarily of foreign income taxes related to income generated by our subsidiaries organized under the laws of the Netherlands and Israel. As we expand the scale of our international business activities, any changes in the U.S. and foreign taxation of such activities may increase our overall provision for income taxes in the future.

We have a valuation allowance for our U.S. deferred tax assets, including federal and state net operating losses. We expect to maintain this valuation allowance until it becomes more likely than not that the benefit of our federal and state deferred tax assets will be realized through expected future taxable income in the U.S.

We regularly review a number of metrics, including the following key operating and financial metrics, to evaluate our business, measure our performance, identify trends in our business, prepare financial projections and make strategic decisions. We believe these non-GAAP and operational measures are useful in evaluating our performance, in addition to our financial results prepared in accordance with U.S. generally accepted accounting principles (“GAAP”). See "— Non-GAAP Financial Measures" for additional information on non-GAAP financial measures and a reconciliation to the most directly comparable financial measures prepared in accordance with U.S. GAAP.

The following table sets forth these metrics as of and for the periods presented:

We define customers as the number of current policyholders underwritten by us or placed by us with third party insurance partners (who pay us recurring commissions) as of the period end date. A customer that has more than one policy count as a single customer for the purposes of this metric. We view customers as an important metric to assess our financial performance because customer growth drives our revenue, expands brand awareness, deepens our market penetration, creates additional upsell and cross-sell opportunities, and generates additional data to continue to improve the functioning of our platform.

We define in force premium (“IFP”) as the aggregate annualized premium for customers as of the period end date. At each period end date, we calculate IFP as the sum of:

i)In force written premium — the annualized premium of in force policies underwritten by us; and

ii)In force placed premium — the annualized premium of in force policies placed with third party insurance companies for which we earn a recurring commission payment. In force placed premium currently reflects approximately 4% of IFP.

The annualized value of premiums is a legal and contractual determination made by assessing the contractual terms with our customers. The annualized value of contracts is not determined by reference to historical revenues, deferred revenues, or any other GAAP financial measure over any period. IFP is not a forecast of future revenues nor is it a reliable indicator of revenue expected to be earned in any given period. We believe that our calculation of IFP is useful to analysts and investors because it captures the impact of growth in customers and premium per customer at the end of each reported period, without adjusting for known or projected policy updates, cancellations, rescissions, and non-renewals. We use IFP because we believe it gives our management useful insight into the total reach of our platform by showing all in force policies underwritten and placed by us. Other companies, including companies in our industry, may calculate IFP differently or not at all, which reduces the usefulness of IFP as a tool for comparison.

We define premium per customer as the average annualized premium customers pay for products underwritten by us or placed by us with third-party insurance partners. We calculate premium per customer by dividing IFP by customers. We view premium per customer as an important metric to assess our financial performance because premium per customer reflects the average amount of money our customers spend on our products, which helps drive strategic initiatives.

We define Annual Dollar Retention (“ADR”), as the percentage of IFP retained over a twelve month period, inclusive of changes in policy value, changes in number of policies, changes in policy type, and churn. To calculate ADR we first aggregate the IFP from all active customers at the beginning of the period and then aggregate the IFP from those same customers at the end of the period. ADR is then equal to the ratio of ending IFP to beginning IFP. We believe that our calculation of ADR is useful to analysts and investors because it captures our ability to retain customers and sell additional products and coverage to them over time. We view ADR as an important metric to measure our ability to provide a delightful end-to-end customer experience, satisfy our customers’ evolving insurance needs and maintain our customers’ trust in our products. Our customers become more valuable to us every year they continue to subscribe to our products. Other companies, including companies in our industry, may calculate ADR differently or not at all, which reduces the usefulness of ADR as a tool for comparison.

Gross earned premium is the earned portion of our gross written premium. Gross earned premium includes direct and assumed premium. We have assumed premium related to car insurance policies written in Texas in connection with our fronting arrangement with a third party carrier in Texas.

We use this operating metric as we believe it gives our management and other users of our financial information useful insight into the gross economic benefit generated by our business operations and allows us to evaluate our underwriting performance without regard to changes in our underlying reinsurance structure. See ‘‘— Components of Our Results of Operations — Revenue — Gross Earned Premium.’’

Unlike net earned premium, gross earned premium excludes the impact of premiums ceded to reinsurers, and therefore should not be used as a substitute for net earned premium, total revenue, or any other measure presented in accordance with GAAP.

Gross profit is calculated in accordance with GAAP as total revenue less loss and loss adjustment expense, net, other insurance expense, and depreciation and amortization (allocated to cost of revenue).

We define adjusted gross profit, a non-GAAP financial measure, as:

•Gross profit, excluding net investment income, interest income and other income, plus

•Employee-related expense, plus

•Professional fees and other, plus

•Depreciation and amortization (allocated to cost of revenue).

See — “Non-GAAP Financial Measures” for a reconciliation of total revenue to adjusted gross profit.

We define adjusted EBITDA, a non-GAAP financial measure, as net loss excluding the impact of income tax expense, depreciation and amortization, stock-based compensation, interest expense, interest income and others, net investment income, amortization of fair value adjustment on insurance contract intangible liability relating to the acquisition of Metromile, and other one time and non-cash adjustments and other transactions that we consider to be unique in nature. See “- Non-GAAP Financial Measures” for a reconciliation of net loss to adjusted EBITDA in accordance with GAAP.

We define gross profit margin, expressed as a percentage, as the ratio of gross profit to total revenue.

We define adjusted gross profit margin, a non-GAAP financial measure, expressed as a percentage, as the ratio of adjusted gross profit to total revenue. See "— Non-GAAP Financial Measures."

We define Ratio of Adjusted Gross Profit to Gross Earned Premium, a non-GAAP financial measure, expressed as a percentage, as the ratio of adjusted gross profit to gross earned premium. Our Ratio of Adjusted Gross Profit to Gross Earned Premium provides management with useful insight into our operating performance. See ‘‘— Non-GAAP Financial Measures.’’

We define gross loss ratio, expressed as a percentage, as the ratio of losses and loss adjustment expense to gross earned premium.

We define net loss ratio, expressed as a percentage, as the ratio of losses and loss adjustment expense, less amounts ceded to reinsurers, to net earned premium.

The following table presents our results of operations:

Net earned premium increased by $165.7 million, or 45%, to $536.3 million for the year ended December 31, 2025 compared to the year ended December 31, 2024 primarily due to the earning of increased gross written premium and impact of our new reinsurance program as discussed in more detail in the “Reinsurance” section above.

Gross written premium increased $242.3 million, or 26%, to $1,171.3 million for the year ended December 31, 2025 compared to the year ended December 31, 2024. The increase was primarily due to a 23% increase in net added customers year over year, driven by the success of our digital advertising campaigns and partnerships. We also continued to expand our geographic footprint and product offerings. In addition, we saw a 7% increase in premiums per customer year over year due to an increasing prevalence of multiple policies per customer, growth in the overall average policy value, and continued shift in the mix of underlying products toward higher value policies. Assumed premium related to car insurance policies written in Texas through our fronting arrangement with a third party carrier in Texas also contributed to the increase in gross written premium during the period.

Ceded written premium decreased $106.1 million, or 21%, to $407.8 million for the year ended December 31, 2025 compared to the year ended December 31, 2024, primarily due to impact of our reinsurance program effective July 1, 2025. See "Reinsurance" above for further information.

Net written premium increased $348.4 million, or 84%, to $763.5 million for the year ended December 31, 2025 compared to the year ended December 31, 2024 due to factors noted above.

The table below shows the amount of premium we earned on a gross and net basis. Ceded earned premium as a percentage of gross earned premium decreased to 49% for the year ended December 31, 2025, as compared to 55% for the year ended December 31, 2024 consistent with our participation rate in our reinsurance contracts as discussed in more detail in the “Reinsurance” section above.

Ceding commission income increased $31.6 million, or 35% to $122.7 million for the year ended December 31, 2025 compared to the year ended December 31, 2024, consistent with the increase in ceded earned premium and impact of our variable ceding commission arrangement with reinsurers driven by favorable loss ratio development in comparison to prior year.

Net investment income increased $3.8 million, or 11%, to $37.8 million for the year ended December 31, 2025 compared to the year ended December 31, 2024. The increase was primarily driven by the diversification of the Company’s investment portfolio with higher returns, offset by investment expenses of $0.4 million. We mainly invest in cash, money market funds, U.S. Treasury bills, corporate debt securities, asset-backed securities, notes and other obligations issued or guaranteed by the U.S. governments and non-US governments.

Commission and other income increased $10.3 million, or 33% to $41.1 million for the year ended December 31, 2025 compared to year ended December 31, 2024, primarily due to growth in premiums placed with third-party insurance companies, installment fees, interest income and sublease income from our New York and San Francisco office space.

Loss and LAE, net increased $70.0 million, or 25%, to $347.0 million for the year ended December 31, 2025 compared to the year ended December 31, 2024. The increase was due to growth in premium offset by reserve releases due to better than expected loss reserve emergence on homeowners multi-peril line of business and car. Net incurred losses included the impact of the California Wildfires in January 2025 in the amount of $19.6 million.

Other insurance expense increased $16.9 million, or 22%, to $93.7 million for the year ended December 31, 2025 compared to the year ended December 31, 2024 consistent with growth in premium and the California FAIR Plan assessment charge of $6.9 million related to the January 2025 California Wildfires. Credit card fees increased $6.5 million, or 37%, as a result of the increase in customers and associated premium. Amortization of deferred acquisition costs, net of ceded commissions also increased by $2.8 million, or 20% as compared to the year ended December 31, 2024, consistent with growth in business. Underwriting data costs increased $2.1 million, or 18%, as compared to the year ended December 31, 2024. Insurance regulatory fees decreased $1.7 million, or 31% as compared to the year ended December 31, 2024.

Sales and marketing expense increased $58.1 million, or 35%, to $224.4 million for the year ended December 31, 2025 compared to the year ended December 31, 2024. Expense related to brand and performance advertising increased by $65.8 million, or 54%, as a result of increased spending on search advertising and other customer acquisition channels. Compensation expense related to the warrant shares decreased $11.7 million, or 180%, as compared to December 31, 2024 due to the termination of the Warrant Agreement with Chewy.

Technology development expense increased $8.1 million, or 9%, to $93.9 million for the year ended December 31, 2025 compared to the year ended December 31, 2024. Employee-related expense, including stock based compensation, net of capitalized costs for the development of internal-use software, increased $9.5 million, or 14%, as compared to the year ended December 31, 2024, driven by increase in headcount and related payroll and stock compensation expense for product, engineering, design and quality assurance personnel. Software expense increase $2.0 million, or 53%, as compared to the year ended December 31, 2024. Hosting and development decreased $1.8 million, or 21%, as compared to the year ended December 31, 2024. Payments made to contractors decreased $1.8 million, or 44%. as compared to the year ended December 31, 2024.

General and administrative expense increased $15.3 million, or 12%, to $139.8 million for the year ended December 31, 2025 compared to the year ended December 31, 2024. Interest expense related to borrowings from financing agreement with GC increased $11.1 million, or 179%, as compared to the year ended December 31, 2024. Bad debt expense increased by $11.1 million, or 101%, as compared to the year ended December 31, 2024. Employee related expense, including stock-based compensation, increased by $10.1 million, or 18%, as compared to the year ended December 31, 2024. Software increased by $1.0 million, or 17%, as compared to the year ended December 31, 2024. Depreciation and amortization expense decreased $4.8 million, or 24%, as compared to year ended December 31, 2024. During the second quarter of 2025, we recorded $11.7 million of tax refund received under the Employee Retention Credit program and $2.3 million of gain on early lease termination related to the Company’s office space in San Francisco.

Income tax expense increased $6.3 million, or 371%, from $1.7 million income tax benefit for the year ended December 31, 2024 to $4.6 million income tax expense for the year ended December 31, 2025, primarily due to a change in uncertain tax positions related to the change in transfer pricing methodology in prior year.

Net loss decreased $36.7 million, or 18%, to $165.5 million for the year ended December 31, 2025 compared to the year ended December 31, 2024 due to the factors described above.

The non-GAAP financial measures below have not been calculated in accordance with GAAP and should be considered in addition to results prepared in accordance with GAAP and should not be considered as a substitute for, or superior to, GAAP results. In addition, adjusted gross profit, adjusted gross profit margin, ratio of adjusted gross profit to gross earned premium, and adjusted EBITDA should not be construed as indicators of our operating performance, liquidity or cash flows generated by operating, investing and financing activities, as there may be significant factors or trends that they fail to address. We caution investors that non-GAAP financial information, by its nature, departs from traditional accounting conventions. Therefore, its use can make it difficult to compare our current results with our results from other reporting periods and with the results of other companies.

Our management uses these non-GAAP financial measures, in conjunction with GAAP financial measures, as an integral part of managing our business and to, among other things: (i) monitor and evaluate the performance of our business operations and financial performance; (ii) facilitate internal comparisons of the historical operating performance of our business operations; (iii) facilitate external comparisons of the results of our overall business to the historical operating performance of other companies that may have different capital structures and debt levels; (iv) review and assess the operating performance of our management team; (v) analyze and evaluate financial and strategic planning decisions regarding future operating investments; and (vi) plan for and prepare future annual operating budgets and determine appropriate levels of operating investments.

We define adjusted gross profit, a non-GAAP financial measure, as gross profit excluding net investment income, interest income and other income, plus fixed costs and overhead associated with our underwriting operations including employee-related expense, professional fees and other, and depreciation and amortization allocated to cost of revenue, and other adjustments that we would consider to be unique in nature. After these adjustments, the resulting calculation is inclusive of only those variable costs of revenue incurred on the successful acquisition of business and without the volatility of investment income. We use adjusted gross profit as a key measure of our progress towards profitability and to consistently evaluate the variable contribution to our business from underwriting operations from period to period.

We define adjusted gross profit margin, a non-GAAP financial measure, expressed as a percentage, as the ratio of adjusted gross profit to total revenue.

The following table provides a reconciliation of total revenue and gross profit margin to adjusted gross profit and the related adjusted gross profit margin, respectively, for the periods presented:

We define the Ratio of Adjusted Gross Profit to Gross Earned Premium as the ratio of adjusted gross profit to gross earned premium. The Ratio of Adjusted Gross Profit to Gross Earned Premium measures the relationship between the underlying business volume and gross economic benefit generated by our underwriting operations, on the one hand, and our underlying profitability trends, on the other. We rely on this measure, which supplements our gross profit ratio as calculated in accordance with GAAP, because it provides management with insight into our underlying profitability trends over time.

We use gross earned premium as the denominator in calculating this ratio, which excludes the impact of premiums ceded to reinsurers, because we believe that it reflects the business volume and the gross economic benefit generated by our underlying underwriting operations, which in turn are the key drivers of our future profit opportunities. We exclude the impact of ceded premiums from the denominator because ceded premiums can change rapidly and significantly based on the type and mix of reinsurance structures we use and, therefore, add volatility that is not indicative of our underlying profitability. For example, a shift to a proportional reinsurance arrangement would result in an increase in ceded premium, with offsetting benefits to gross profit from ceded losses and ceding commissions earned, resulting in a nominal overall economic impact. This shift would result in a steep decline in total revenue with a corresponding spike in gross margin, whereas we expect that the Ratio of Adjusted Gross Profit to Gross Earned Premium would remain relatively unchanged. We expect our reinsurance structure to evolve along with our costs and capital requirements, and we believe that our reinsurance structure at a given time does not reflect the performance of our underlying underwriting operations, which we expect to be the key driver of our costs of reinsurance over time.

On the other hand, the numerator, which is adjusted gross profit, includes the net impact of all reinsurance, including ceded premiums and the benefits of ceded losses and ceding commissions earned. Because our reinsurance structure is a key component of our risk management and a key driver of our profitability or loss in a given period, we believe this is meaningful.

Therefore, by providing this Ratio of Adjusted Gross Profit to Gross Earned Premium for a given period, we are able to assess the relationship between business volume and profitability, while eliminating the volatility from the cost of our then-current reinsurance structure, which is driven primarily by the performance of our insurance underwriting platform rather than our business volume.

The following table sets forth our calculation of the Ratio of Adjusted Gross Profit to Gross Earned Premium for the periods presented:

We define Adjusted EBITDA, a non-GAAP financial measure, as net loss excluding income tax expense, depreciation and amortization, stock-based compensation, interest expense, interest income and others, net investment income, amortization of fair value adjustment on insurance contract intangible liability relating to the acquisition of Metromile, and other one time and non-cash adjustments and other transactions that we would consider to be unique in nature. We exclude these items from Adjusted EBITDA because we do not consider them to be directly attributable to our underlying operating performance. We use Adjusted EBITDA as an internal performance measure in the management of our operations because we believe it gives our management and other customers of our financial information useful insight into our results of operations and our underlying business performance. Adjusted EBITDA should not be viewed as substitute for net loss calculated in accordance with GAAP, and other companies may define adjusted EBITDA differently.

The following table provides a reconciliation of Adjusted EBITDA to net loss for the periods presented.

(1) Includes the impact of canceled unvested warrant shares for contract year 2 related to the termination of the Warrant Agreement with Chewy of $5.2 million for the year ended December 31, 2025 and compensation expense related to the warrant shares of $6.5 million for the year ended December 31, 2024, respectively (See Note 16 of the consolidated financial statements).

(2) Includes the California FAIR Plan assessment of $6.9 million related to the January 2025 California Wildfires for the year ended December 31, 2025 (See Note 20 of the consolidated financial statements).

(3) Includes $11.7 million of tax refund received under the Employee Retention Credit Program for the year ended December 31, 2025 (See Note 17 of the consolidated financial statements).

(4) Includes $2.3 million of gain on early lease termination related to the Company's office space in San Francisco for the year ended December 31, 2025 (See Note 21 of the consolidated financial statements).

(5) Includes $1.0 million of gain from settlement of previously disclosed data security matter for the year ended December 31, 2025 (See Note 20 of the consolidated financial statements).

(6) Includes $3.9 million extra-contractual car claim liability related to pre-acquisition Metromile (see Note 12 of the consolidated financial statements), and impairment charge of $0.3 million related to a portion of the New York office sublease, net of gain on termination of lease for the year ended December 31, 2024 (See Note 21 of the consolidated financial statements).

As of December 31, 2025, we had $385.0 million in cash and cash equivalents, and $722.9 million in investments. From the date we commenced operations, we have generated negative cash flows from operations, and we have financed our operations primarily through private and public sales of equity securities and third-party financing. Our principal sources of funds are insurance premiums, investment income, reinsurance recoveries and proceeds from maturity and sale of invested assets. These funds are primarily used to pay claims, operating expenses and taxes. We entered into an Agreement with GC in June 2023, where up to $150 million of financing would be provided for our sales and marketing growth efforts through December 31, 2024. The Agreement was amended and restated in January 2024, pursuant to which an additional financing of $140 million would be provided for our sales and marketing growth efforts through December 31, 2025, and was further amended and restated in April 2024 and June 2024 to clarify certain provisions and all material terms and conditions remain unchanged. On February 3, 2025, the Agreement was further amended under which GC will provide up to an additional $200 million of financing for our sales and marketing growth efforts from January 1, 2026 to December 31, 2026. As of December 31, 2025, we had $158.1 million of outstanding borrowings under the Amended and Restated Agreement with GC. We believe our existing cash and cash equivalents as of December 31, 2025 will be sufficient to meet our working capital, liquidity and capital expenditure needs over at least the next 12 months. This Agreement with GC was further amended and restated in December 2025 to clarify certain provisions with no changes to material terms. This belief is subject, to a certain extent, on general economic, financial, competitive, regulatory and other factors that are beyond our control.

Our cash flows used in operations may differ substantially from our net loss due to non-cash charges or due to changes in balance sheet accounts.

The timing of our cash flows from operating activities can also vary among periods due to the timing of payments made or received. Some of our payments and receipts, including loss settlements and subsequent reinsurance receipts, can be significant. Therefore, their timing can influence cash flows from operating activities in any given period. The potential for a large claim under an insurance or reinsurance contract means that our insurance subsidiaries may need to make substantial payments within relatively short periods of time, which would have a negative impact on our operating cash flows.

We are a holding company that transacts a majority of our business through operating subsidiaries. Consequently, our ability to pay dividends to stockholders, meet debt payment obligations and pay taxes and operating expenses is largely dependent on dividends or other distributions from our subsidiaries and affiliates, whose ability to pay us is highly regulated.

Our U.S. and Dutch insurance company subsidiaries, and our Dutch insurance holding company, are restricted by statute as to the amount of dividends that they may pay without the prior approval of their respective competent regulatory authorities. As of December 31, 2025, cash and investments held by these companies was $773.0 million and statutory surplus amounted to $329.8 million.

Insurance companies in the United States are also required by state law to maintain a minimum level of policyholder's surplus. Insurance regulators in the states in which we operate have a risk-based capital standard designed to identify property and casualty insurers that may be inadequately capitalized based on inherent risks of the insurer's assets and liabilities and its mix of net written premium. Insurers falling below a calculated threshold may be subject to varying degrees of regulatory action. As of December 31, 2025, the total adjusted capital of our U.S. insurance subsidiaries was in excess of its respective prescribed risk-based capital requirements.

The following table summarizes our cash flow data for the periods presented: