AMENDMENT NO. 1 TO THE AMENDED AND RESTATED QUOTA SHARE REINSURANCE AGREEMENT This Amendment No. 1 (this “Amendment”) to the Amended and Restated Quota Share by and between American Family Mutual Insurance Company, S.I. (the “Company”) and Bowhead Insurance Company, Inc. (the “Reinsurer”) dated the 23rd day of May, 2024 (the “Agreement”) is effective 12:01 am Eastern Time as of 4th day of May 2026 (the “Amendment Effective Date”). WITNESSETH: THAT, in consideration of the mutual covenants hereinafter contained and upon the terms and conditions hereinbelow set forth, the parties hereto agree as follows: PREAMBLE WHEREAS, the Company and the Reinsurer entered into a quota share reinsurance agreement dated as of January 1, 2021 (the “Original Agreement”), and subsequently amended and restated that agreement by entering into the Agreement on the May 23, 2024. WHEREAS, the Company and Reinsurer desire to amend certain terms in the Agreement. Section 1. Defined Terms As used herein, each term defined in the Agreement shall have the meaning assigned thereto in the Agreement, unless expressly provided herein to the contrary. Section 2. Amendments 2.1 Limits. Section 4.02(i) of the Agreement shall be amended and restated in its entirety as follows: (i) By the Company upon three hundred sixty five (365) days’ notice if the aggregate gross written premium produced by or through Agent under the Agency Agreements and ceded to the Reinsurer under this Agreement exceeds $1,500,000,000 in the aggregate during any calendar year and the Company and the Reinsurer have not reached a mutually acceptable agreement within ninety (90) days of the Reinsurer’s receipt of such notice. During the period from the date the Reinsurer received a notice of termination under this Section 4.02 until such termination, the parties may discuss an extension or amendment of the terms of this Agreement. 2.2 Obligations. Section 5.06(a)(vi) of the Agreement shall be amended and restated in its entirety as follows: “Obligations” within this Article V shall, if the Reinsurer is licensed

or accredited as required to provide the Company with full credit for the reinsurance ceded hereunder in the Company’s statutory financial statements, include: (A) Reinsured losses and allocated loss expenses paid or payable by the Company, but not recovered from the Reinsurer; (B) Reserves for reinsured losses reported and outstanding; (C) Reserves for reinsured losses incurred but not reported; and (D) Reserves for allocated reinsured loss expenses; and (E) (1) starting as of June 30, 2026 until September 29, 2026, Reserves for 55% of unearned premiums; (2) starting as of September 30, 2026 through and until December 30, 2026, Reserves for 70% of unearned premiums; (3) starting as of December 31, 2026 through and until March 30, 2027, Reserves for 85% of unearned premiums; and (4) starting March 31, 2027, 100% of unearned premiums; provided, however, for each of the foregoing clauses (1)-(4), that this amount may be reduced by an amount, determined by the Reinsurer in good faith to be no more than strictly necessary to prevent the Reinsurer and its affiliates from (i) breaching any liquidity covenant under any credit facility that supports the Reinsurer’s operations or (ii) having insufficient liquidity for the day to-day operations of the Reinsurer and its affiliates; provided that, the establishment of reserves for purposes of the definition of “Obligations,” and the determination of corresponding funding of security for such Obligations provided in Section 5.03, shall both be set by the Reinsurer, reasonably, in good faith and in accordance with SAP, determined net of any and all inuring reinsurance purchased by the Reinsurer for the Subject Business (the “Inuring Reinsurance”); provided further, that (1) the Reinsurer shall be obligated to instruct all such Inuring Reinsurance retrocessionaires that any funds paid, payable or advanced to the Reinsurer in respect of any such Inuring Reinsurance shall be immediately deposited directly into the Trust Account or the Claims Payment Account, as directed in writing by the Company from time to time, and at any time, and (2) the Reinsurer shall not take any action that would redirect any such Inuring Reinsurance recovery or payment other than to the

Trust Account or the Claims Payment Account, as provided in the immediately preceding clause, without the express written direction of the Company. If the Reinsurer breaches this Section 5.06, the Company shall have the right to terminate this Agreement pursuant to Section 4.02(h), subject to the applicable cure period provided therein. If the Reinsurer is not licensed or accredited as required to provide the Company with full credit for the reinsurance ceded hereunder in the Company’s statutory financial statements, the term “Obligations” within this Article V shall include: (A) Reinsured losses and allocated loss expenses paid or payable by the Company, but not recovered from the Reinsurer; (B) Reserves for reinsured losses reported and outstanding; (C) Reserves for reinsured losses incurred but not reported; and (D) Reserves for allocated reinsured loss expenses and unearned premiums; provided, that the establishment of reserves for purposes of the definition of “Obligations,” and the determination of corresponding funding of security for such Obligations provided in Section 5.03, shall both be set by the Company, reasonably, in good faith and in accordance with SAP, determined gross of any and all Inuring Reinsurance. 2.3 Commissions. Section 8.02 of the Agreement shall be amended and restated in its entirety as follows: 8.02 It is understood that the Reinsurer shall pay the Company directly within thirty (30) days following the end of each month (or with respect to the first such month, the first month ending after the execution and delivery of the Original Agreement in respect of the period since November 1, 2020 to such month end), as a Ceding Fee (the “Ceding Fee”), an amount equal to 2% of the Net Premium reported by the Reinsurer per month; provided, that beginning on the date that as of 12:01 am Eastern Standard Time is: (a) twelve (12) months after the Date of Determination, the Ceding Fee shall increase to 2.75%; (b) twenty-four (24) months after the Date of Determination, the Ceding Fee shall increase to 3.25%; and (c) thirty-six (36) months after the Date of Determination, the Ceding Fee shall increase to 5.0%:

provided, however, in (i) the fiscal year ending December 31, 2027, the Ceding Fee for any Net Premium transacted and effective during such calendar year in excess of $1,000,000,000 shall be 5.75%; and (ii) any fiscal year commencing on or after January 1, 2028, the Ceding Fee for any Net Premium transacted and effective during such calendar year in excess of $1,000,000,000 shall be 6.5%. On the date that is sixty (60) months after the Date of Determination, if the Company has not exercised its right of termination under Section 4.02(a)(i), the Company and the Reinsurer shall seek to agree on a new Ceding Fee applicable on and after such date; provided, that if the Parties do not agree on a new Ceding Fee, the Company shall have the right to terminate this Agreement pursuant to Section 4.02(a)(ii). 2.4 Notices. Section 21.01 of the Agreement shall be amended and restated in its entirety as follows: 21.01 All notices required to be given hereunder shall be deemed to have been duly given by personally delivering such notice in writing or by sending it by a delivery service or by mailing it, Certified Mail, return receipt requested, with postage prepaid to the address as shown below. Any party may change the address to which notices and other communications hereunder are to be sent to such party by giving the other party written notice thereof in accordance with this provision. To the Company: American Family Mutual Insurance Company, S.I. 6000 American Parkway, Madison, WI 53783 Thomas.Hrdlick@amfam.com Attention: Thomas Hrdlick Copy To: Parr.Schoolman@amfam.com Attention: Parr Schoolman To the Reinsurer: Bowhead Insurance Company, Inc. 452 Fifth Avenue, 24th Floor New York, NY 10018 regulatory-legal@bowheadspecialty.com Attention: Office of the General Counsel Section 3. Miscellaneous. 3.1. No Other Amendments; Effectiveness. Except as expressly amended and/or superseded by this Amendment, the Agreement remains and shall remain in full force and effect. This Amendment shall not constitute an amendment or waiver of any provision of the Agreement, except as expressly set forth herein. Upon the execution and delivery hereof, the Agreement shall thereupon be deemed to be amended and supplemented as hereinabove set forth as fully and with the same effect as if the amendments and supplements made hereby were originally set forth

in the Agreement. This Amendment and the Agreement shall each henceforth be read, taken and construed as one and the same instrument, but such amendments and supplements shall not operate so as to render invalid or improper any action heretofore taken under the Agreement. If and to the extent there are any inconsistencies between the Agreement and this Amendment with respect to the matters set forth herein, the terms of this Amendment shall control. References in the Agreement to the Agreement shall be deemed to mean the Agreement as amended by this Amendment. On and after the Amendment Effective Date, each reference to the Agreement, “this Agreement”, “hereof”, “hereunder”, “herein” or words of like import referring to the Agreement shall mean and be a reference to the Agreement as amended hereby provided, that references in the Agreement to “the date hereof” or “the date of this Agreement” or words of like import shall continue to refer to the date of May 23, 2024. 3.2. Sections of the Agreement. Section 21.02, Section 21.04, Section 21.05, Section 21.06, Section 21.07, Section 21.08, Section 21.15, Section 21.16 and Section 21.17 of the Agreement are each hereby incorporated by reference mutatis mutandis. [Signature Page Follows]

IN WITNESS WHEREOF, the parties have caused this Amendment to be executed by their respective officers duly authorized so to do, and their respective corporate seals to be attached hereto as of the date and year first above written. AMERICAN FAMILY MUTUAL INSURANCE COMPANY, S.I. By: ___/s/ Troy Van Beek_________________ Name: Troy Van Beek Title: Enterprise Chief Financial Officer and Treasurer as the Company BOWHEAD INSURANCE COMPANY, INC. By: ___/s/ Stephen Sills__________________ Name: Stephen Sills Title: Chief Executive Officer and President as the Reinsurer [Signature page to the 1st Amendment to the Amended and Restated Quota Share Reinsurance Agreement]

AMENDMENT NO. 1 TO THE AMENDED AND RESTATED INSURANCE TRUST AGREEMENT This Amendment No. 1 (this “Amendment”) to the Amended and Restated Insurance Trust Agreement among Bowhead Insurance Company, Inc. a corporation organized under the laws of Wisconsin (the “Grantor”), American Family Mutual Insurance Company, S.I., a corporation organized under the laws of Wisconsin (the “Beneficiary”), and U.S. Bank National Association, as trustee (the “Bank”) effective as of 23rd day of May, 2024 (the “Existing Agreement”). WITNESSETH: THAT, in consideration of the mutual covenants hereinafter contained and upon the terms and conditions hereinbelow set forth, the parties hereto agree as follows: PREAMBLE WHEREAS, the Grantor, the Beneficiary and the Bank previously entered into a trust agreement in March of 2021, and subsequently amended and restated that agreement by entering into the Existing Agreement. WHEREAS, the Grantor, the Beneficiary and the Bank desire to amend certain terms in the Existing Agreement. Section 1. Defined Terms As used herein, each term defined in the Existing Agreement shall have the meaning assigned thereto in the Existing Agreement, unless expressly provided herein to the contrary. Section 2. Amendments 2.1 Obligations. Section 1.28 of the Existing Agreement shall be amended and restated in its entirety as follows: 1.28 “Obligations” shall, (A), if the Grantor is licensed or accredited as required to provide the Beneficiary with full credit for the reinsurance ceded pursuant to the Reinsurance Agreement, include: a. Reinsured losses and allocated loss expenses paid or payable by the Beneficiary, but not recovered from the Grantor; b. Reserves for reinsured losses reported and outstanding; c. Reserves for reinsured losses incurred but not reported; and d. Reserves for allocated reinsured loss expenses; and

e. (1) starting as of June 30, 2026 until September 29, 2026, Reserves for 55% of unearned premiums; (2) starting as of September 30, 2026 through and until December 30, 2026, Reserves for 70% of unearned premiums; (3) starting as of December 31, 2026 through and until March 30, 2027, Reserves for 85% of unearned premiums; and (4) starting March 31, 2027, 100% of unearned premiums; provided, however, for each of the foregoing clauses (1)-(4), that this amount may be reduced by an amount, determined by the Grantor in good faith to be no more than strictly necessary to prevent the Grantor and its affiliates from (i) breaching any liquidity covenant under any credit facility that supports the Grantor’s operations or (ii) having insufficient liquidity for the day to-day operations of the Grantor and its affiliates; provided that, the establishment of reserves for purposes of the definition of “Obligations,” and the determination of corresponding funding of security for such Obligations, shall both be set by the Grantor, reasonably, in good faith and in accordance with SAP, determined net of any and all Inuring Reinsurance (as defined in the Reinsurance Agreement). (B) If the Grantor is not licensed or accredited as required to provide the Beneficiary with full credit for the reinsurance ceded pursuant to the Reinsurance Agreement, the term “Obligations” shall include: a. Reinsured losses and allocated loss expenses paid or payable by the Beneficiary, but not recovered from Grantor; b. Reserves for reinsured losses reported and outstanding; c. Reserves for reinsured losses incurred but not reported; and d. Reserves for allocated reinsured loss expenses and unearned premiums; provided, that the establishment of reserves for purposes of the definition of “Obligations,” and the determination of corresponding funding of security for such Obligations, shall be set by the Beneficiary, reasonably, in good faith and in accordance with SAP, determined gross of any and all Insuring Reinsurance.

2.2 Reinsurance Agreement. Section 1.33 of the Existing Agreement shall be amended and restated in its entirety as follows: 1.33 "Reinsurance Agreement" means the Amended and Restated Quota Share Reinsurance Agreement entered into as of 23rd day of May, 2024 with effect as at 12:01 a.m. Eastern Standard Time, on November 1, 2020, by and between the Beneficiary and the Grantor, as may be amended from time to time. 2.3 Guidelines. 2.3.1 Section 3.4.1.1 of the Existing Agreement shall be amended and restated in its entirety as follows: 3.4.1.1 Guidelines; Cash-flow Analysis. The Grantor and the Beneficiary hereby reserve to the Grantor sole discretion to determine the Guidelines; to establish and carry out a Cash-flow Analysis consistent with the requirements of applicable law; and to deliver the Guidelines, the Cash-flow Analysis, and this Agreement to each person that has discretion to manage the Assets. The Grantor and the Beneficiary hereby represent and warrant that (i) the Guidelines, the Cash-flow Analysis, and the permissible investments set forth herein are the only investment restrictions imposed upon the Account by the Grantor or the Beneficiary; (ii) following such restrictions will not cause a violation of any applicable law; and (iii) a copy the Guidelines (as may be amended from time to time) are attached as Exhibit B (Guidelines) to hereto. 2.3.2 Exhibit B of the Existing Agreement shall be replaced in its entirety by Exhibit 1 attached to this Amendment. 2.4 Delivery of Directions. Section 13.13.2 of the Agreement shall be amended and restated in its entirety as follows: 13.13.2 Any direction, notice, or other communication to or from the Beneficiary provided for in this Agreement will be given in writing and (i) unless the recipient has timely delivered a superseding address under this Agreement, addressed as provided under this Agreement, (ii) entered into the Beneficiary's account in the Bank's on-line portal, or (iii) sent to the Bank by Messaging System. If to the Grantor: Authorized Officer: c/o Brad Mulcahey U.S. Mailing Address: 452 Fifth Avenue, 24th Floor New York, NY 10018 Email Address: bmulcahey@bowheadspecialty.com

If to the Beneficiary: Authorized Officer: c/o Parr Schoolman U.S. Mailing Address: 6000 American Parkway Madison, WI 53783 Email Address: Parr.Schoolman@amfam.com If to the Bank: Authorized Officer: c/o Dan Pace Vice President and Relationship Manager U.S. Mailing Address: 1 Federal Street, Boston, MA 02110 Email Address: daniel.pace@usbank.com Section 3. Miscellaneous. 3.1. No Other Amendments; Effectiveness. Except as expressly amended and/or superseded by this Amendment, the Existing Agreement remains and shall remain in full force and effect. This Amendment shall not constitute an amendment or waiver of any provision of the Existing Agreement, except as expressly set forth herein. Upon the execution and delivery hereof, the Existing Agreement shall thereupon be deemed to be amended and supplemented as hereinabove set forth as fully and with the same effect as if the amendments and supplements made hereby were originally set forth in the Existing Agreement. This Amendment and the Existing Agreement shall each henceforth be read, taken and construed as one and the same instrument, but such amendments and supplements shall not operate so as to render invalid or improper any action heretofore taken under the Existing Agreement. If and to the extent there are any inconsistencies between the Existing Agreement and this Amendment with respect to the matters set forth herein, the terms of this Amendment shall control. On and after the Amendment Effective Date, each reference to the Agreement, “this Agreement”, “hereof”, “hereunder”, “herein” or words of like import referring to the Agreement shall mean and be a reference to the Agreement as amended hereby provided, that references in the Agreement to “the date hereof” or “the date of this Agreement” or words of like import shall continue to refer to the date of May 23, 2024. 3.2. Sections of the Agreement. Section 13.4, Section 13.6, Section 13.7, Section 13.21 and Section 13.22 of the Existing Agreement are each hereby incorporated by reference mutatis mutandis. [Signature Page Follows]

IN WITNESS WHEREOF, an authorized officer of each party hereby executes this Amendment on the date stated beneath that party’s signature. THE GRANTOR: By: /s/ Brad Mulcahey____________________________ (Signature of the Grantor’s authorized officer) Brad Mulcahey ______________________________ (Printed name of the Grantor’s authorized officer) Its: Chief Financial Officer and Treasurer __________ (Title of the Grantor’s authorized officer) Dated: May 4, 2026______________________________ THE BENEFICIARY: By: /s/ Troy Van Beek___________________________ (Signature of the Beneficiary’s authorized officer) Troy Van Beek______________________________ (Printed name of the Beneficiary’s authorized officer) Its: _Enterprise Chief Financial Officer and Treasurer__ (Title of the Beneficiary’s authorized officer) Dated: May 4, 2026 _______________________________ THE BANK: By: /s/ Daniel Pace_______________________________ (Signature of the Bank’s authorized officer) _Daniel Pace______________________________ (Printed name of the Bank’s authorized officer) Its: Vice President and Relationship Manager_________ (Title of the Bank’s authorized officer) Dated: May 4, 2026 _______________________________ [Signature page to Amendment No. 1 to the Amended and Restated Insurance Trust Agreement]

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 2 Forward-Looking Statements and Other Notices This presentation has been prepared by Bowhead Specialty Holdings Inc. (“we,” “us,” “our,” “Bowhead” or the “Company”) on a confidential basis for the exclusive use of the party to whom Bowhead delivers this presentation. This presentation has been prepared by Bowhead for informational purposes only and not for any other purpose. Nothing contained in this presentation is, or should be construed as, a recommendation, promise or representation by the presenter or Bowhead or any officer, director, employee, agent or advisor of Bowhead. This presentation does not purport to be all inclusive or to contain all of the information you may desire. Information provided in this presentation speaks only as of the date hereof. Bowhead assumes no obligation to update any information or statement after the date of this presentation as a result of new information, subsequent events, or any other circumstances. We request that you keep any information at this meeting confidential and that you do not disclose any of the information to any other parties without the Company's prior express written permission. This presentation contains “forward-looking statements” within the meaning of the Private Securities Litigation Reform Act of 1995. All statements other than statements of historical facts contained in this presentation, including statements regarding our future results of operations or financial condition, business strategy and plans, and objectives of management for future operations are forward-looking statements. Some of the forward-looking statements can be identified by the use of terms such as “believes”, “expects”, “may”, “will”, “should”, “could”, “seeks”, “intends”, “plans”, “estimates”, “anticipates” or other comparable terms. However, not all forward-looking statements contain these identifying words. These forward-looking statements include all matters that are not related to present facts or current conditions or that are not historical facts. They appear in a number of places throughout this presentation and include statements regarding our intentions, beliefs or current expectations concerning, among other things, our consolidated results of operations, financial condition, liquidity, prospects and growth strategies and the industries in which we operate, and include, without limitation, statements relating to our future performance. Forward-looking statements are subject to known and unknown risks and uncertainties, many of which are beyond our control. Our actual results may differ materially from those expressed in, or implied by, the forward-looking statements included in this presentation as a result of various factors, including, among others, the factors discussed under the heading “Risk Factors” in our Annual Report on Form 10-K for the year ended December 31, 2025, as well as our other filings with the Securities and Exchange Commission. The forward-looking statements made in this presentation relate only to events as of the date on which the statements are made. We undertake no obligation to update any forward-looking statements made in this presentation to reflect events or circumstances after the date of this presentation or to reflect new information or the occurrence of unanticipated events, except as required by law. We may not actually achieve the plans, intentions, or expectations disclosed in our forward-looking statements, and you should not place undue reliance on our forward-looking statements. Unless otherwise indicated, information contained in this presentation concerning our industry and the markets in which we operate, including our general expectations, market position and market opportunity, is based on our management’s estimates and research, as well as industry and general publications and research, surveys and studies conducted by third parties. Industry publications, studies and surveys generally state that they have been obtained from sources believed to be reliable, although they do not guarantee the accuracy or completeness of such information. We believe that the information from these third-party publications, research, surveys and studies included in this presentation is reliable. Management’s estimates are derived from publicly available information, their knowledge of our industry and their assumptions based on such information and knowledge, which we believe to be reasonable. This data involves a number of assumptions and limitations which are necessarily subject to a high degree of uncertainty and risk due to a variety of factors. These and other factors could cause our future performance to differ materially from our assumptions and estimates. This presentation contains references to our trademarks and service marks and to those belonging to other entities. Solely for convenience, trademarks and trade names referred to in this presentation may appear without the ® or TM symbols, but such references are not intended to indicate, in any way, that we will not assert, to the fullest extent under applicable law, our rights or the rights of the applicable licensor to these trademarks and trade names. We do not intend our use or display of other companies’ trade names, trademarks or service marks to imply a relationship with, or endorsement or sponsorship of us by, any other companies. “Non-admitted” or excess and surplus (“E&S”) lines refers to policies generally not subject to regulations governing premium rates or policy language. We also consider business written on (i) a facultative reinsurance basis or (ii) an admitted basis through either the New York Free Trade Zone or similar commercial deregulation exemptions available in certain jurisdictions, to be E&S business since such business is generally free of rate and form restrictions. This presentation contains certain financial measures that are not presented in accordance with generally accepted accounting principles in the United States (“U.S. GAAP”). Under U.S. securities laws, these measures are called “non-GAAP financial measures.” We use these non-GAAP financial measures when planning, monitoring and evaluating our performance. We believe these non-GAAP financial measures give our management and other users of our financial information useful insight into our underlying business performance. You should not rely on these non-GAAP financial measures as a substitute for any U.S. GAAP financial measure. While we believe that these non-GAAP financial measures are useful in evaluating our business, this information should be considered supplemental in nature and is not meant to be an alternative to our reported results prepared in accordance with U.S. GAAP. In addition, other companies, including companies in our industry, may calculate such measures differently, which reduces their usefulness as comparative measures. For a reconciliation of such non-GAAP financial measures to the most directly comparable U.S. GAAP financial measures, see the Appendix of this presentation.

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 3 Our Key Investment Highlights Focused on profitable, growing lines in attractive E&S market Ability to deliver differentiated profitability across market cycles Strong underwriting culture with fully-integrated and accountable value chain Highly experienced and entrepreneurial management team Clean balance sheet with no reserves from accident years prior to 2020 Deep, long-standing distribution relationships based on expertise, service and mutual benefit Commitment to long-term value generates strong returns, making us well-positioned for continued growth

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 4 Bowhead: Who We Are Growing and profitable E&S focused specialty P&C business founded and led by industry veteran, Stephen Sills, and supported through a strategic partnership with American Family Mutual Insurance Company, S.I. (“AmFam”) Underwriting-First Culture led by leaders with proven track records “Craft” Tailored solutions in markets with attractive pricing and terms Cycle Management Sustainable underwriting across market cycles “Digital” Tech-enabled underwriting emphasizing speed and disciplined decision making

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 5 Bowhead: By the Numbers Key highlights4 underwriting divisions Q1'26 GWP: $217MM 68% 13% Professional Liability 14% Casualty Healthcare Liability 95.3% Q1'26 Combined Ratio1 14.1% Q1'26 Adjusted ROE2 $217MM Q1'26 GWP 83% Q1'26 GWP written on E&S basis 30+ Leadership team average years of experience3 48% Q1'21 through Q1'26 GWP CAGR 5% Baleen Specialty Note: 1 Combined ratio for the three months ended March 31, 2026 was comprised of a 66.9% loss ratio and a 28.4% expense ratio. 2 Adjusted ROE is calculated by annualizing the three months ended March 31, 2026 adjusted net income, divided by the average of mezzanine and stockholders’ equity as of December 31, 2025 and March 31, 2026. Adjusted net income and adjusted ROE are Non-GAAP financial measures. See “Non-GAAP Reconciliation” on slide 20 for a reconciliation of the non-GAAP financial measure to the most directly comparable U.S. GAAP measure; 3 Leadership team includes Stephen Sills, David Newman, Derek Broaddus, Daniel Gamble, Joe Calcagno and Brandon Mezick.

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 6 Highly Experienced and Entrepreneurial Management Team Name and position Years of industry experience Leadership role prior to joining Bowhead Prior professional experience Stephen Sills Founder and CEO 40+ Chairman and CEO of CapSpecialty David Newman Chief Underwriting Officer 40+ Chief Underwriting Officer of Allied World’s Global Markets division Brad Mulcahey Chief Financial Officer 23 Chief Financial Officer of Berkley Select, a division of W.R. Berkley Corp Steve Feltner Chief Operating Officer 15 Vice President, Strategic Finance & Planning at Horace Mann Ayla Boyd, FCAS Chief Actuary 17 Actuarial Manager at Ironshore Insurance Derek Broaddus Head of Casualty 30 Senior Vice President at Allied World Chris Butler, JD Head of Claims 26 Managing Director, Professional Liability Claims at Markel Joe Calcagno Head of Healthcare Liability 23 Vice President, Healthcare at Sompo International – Sompo America Dan Gamble Head of Professional Liability 31 Managing Director, Management & Professional at Markel Brandon Mezick Head of Digital Underwriting 17 Chief Operating Officer of IronHealth at Ironshore Executive Risk

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 7 $27 $28 $29 $29 $31 $34 $39 $46 $61 $73 $85 $95 $102 44.6% 50.4% 49.0% 57.8% 70.9% 63.9% 60.5% 67.9% 62.6% 61.0% 51.0% 53.0% 50.3% DPW Loss ratio 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 2025 Focused on Profitable, Growing Lines in Attractive E&S Market Expanding Commercial E&S Market ($Bn) Bowhead launch (September 2020) Source: S&P Global; Note: E&S premiums sourced per S&P Global based on license types in Schedule T of statutory filings ’20-’25 DPW CAGR: 16% ’20-’25 Avg. Loss Ratio: 57.6%

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 8 100% 100% 80% 45% 39% 37% 30% 25% 14% Focused on Profitable, Growing Lines in Attractive E&S Market (cont’d) E&S Market Share 3 0.7%4 0.8%1.9% 0.7%0.9% 4.2% 3.9% 1.4% E&S Concentration1 2 Source: Company filings, S&P Global. 1 Represents 2025 statutory direct written premiums as a % of 2025 U.S. GAAP GWP; 2 Markel U.S. GAAP GWP includes program services and fronting. 3 Represents 2025 SNL P&C Groups and Affiliated Cos E&S statutory direct written premium as a % of industry total for 2025. 4 Represents American Family Insurance (SNL P&C Group) 2025 statutory E&S direct written premium. 0.5%

9 Business Mix vs. Specialty Peers GWP CAGR (2021-2024) Source: Company filings, S&P Global. 1 Represents statutory premium for each company's SNL P&C Group. Long-Tail lines include Commercial Multi Peril, Fidelity & Surety, Medical Professional Liability, Other/Product Liability, and Workers’ Compensation. Short-Tail lines include Accident & Health, Aircraft, Commercial Auto, Financial & Mortgage Guaranty, Fire & Allied, Homeowners/Farmowners, Marine Lines, Other Commercial, and Private Auto. 2025 Long-Tail Premium as a % of Total Premium1 1 77.2%95.7% 75.9%3-Year Average Combined Ratio 90.8%85.5%90.2% 96.3% 90.9% 2025 Long-Tail Premium as a % of Total Premium Bowhead writes a low volatility book of business that produces consistent and profitable results 100% 77% 70% 70% 62% 58% 54% 49% 35% 93.2%

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 10 Strong Underwriting Culture with Fully-Integrated and Accountable Value Chain In-house underwriting expertise Underwriting solutions and product development Integrated actuarial, claims and legal Comprehensive reinsurance program Customized technology platform Long-term distribution relationships • We generally do not delegate underwriting to outside parties, which is a key component of our fully-integrated model • Our unique platform allows us to deliver our custom solutions to clients, while consistently generating underwriting profit across our business

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 11 Craft Products at Founding Craft Products Today Excess Practice Excess Projects Primary Practice Primary Projects Excess Other¹ Primary Other Private D&O E&O Public D&O Financial Institutions Cyber Hospitals Senior Care Managed Care HCML Misc. Medical Facilities Casualty Professional Liability Healthcare Liability D&O Highly experienced team with previous leadership positions at leading insurance companies Specific subject matter experts with proven track records of generating underwriting profits within the lines they write Created primary capabilities across all our products as part of cycle management strategy Strong and disciplined underwriting culture built around rigorous analytical tools (“BRATs”) and cross-functional collaboration (“Roundtables”) Our Key Value Proposition: Underwriting Matters Note: 1 Excess Other includes Public Entity Environmental Digital Evolution: Craft & Digital Bowhead Digital Express Baleen Specialty Ability to Deliver Differentiated Profitability Across Market Cycles

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 12 Clean Balance Sheet with No Reserves from Accident Years Prior to 2020 • 100% cash, short-term investments and investment grade portfolio with no equity or alternative investment risk • Fixed income book and market yields of 4.6% and 4.7% respectively as of March 31, 2026 • Weighted average effective duration of 3.2 years and an average credit rating of “AA-” as of March 31, 2026Conservative investment portfolio • Diversified and attractive commercial specialty P&C portfolio with no property or natural-catastrophe exposure • Reflects continuously favorable rate environment with no business or reserves from pre-2020 accident years Free from legacy reserves • No intangibles • 400%+ RBC ratio as of December 31, 2025 • All reinsurers have A.M. Best rating of “A” or better as of March 31, 2026Prudent financial profile

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 13 Robust growth and commitment to long-term value creation Note: 1 Non-GAAP financial measure. See “Non-GAAP Reconciliation” on slide 20 for a reconciliation of the non-GAAP financial measure in accordance with the most comparable U.S. GAAP measure. Robust growth Attractive profitability Strong returns Adjusted ROE1Combined Ratio Excess Practice Excess Projects Primary Practice Primary Projects Excess Other Primary Other Private D&O E&O Public D&O Financial Institutions Cyber Hospitals Senior Care Managed Care 95.8% 96.5% 95.3% 64.4% 66.7% 66.9% 31.4% 29.8% 28.4% Expense Ratio Loss Ratio 2024 2025 Q1'26 HCML MMF 15.2% 13.6% 14.1% 2024 2025 Q1'26 $56$43 $16 Adj. net income ($MM)1 $224 $357 $508 $696 $863 Casualty Professional Liability Healthcare Liability Baleen Specialty 2021 2022 2023 2024 2025 40% CAGR $175 $217 Q1'25 Q1'26 24% CAGR GWP ($MM)

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 14 Well-Positioned to Manage Underwriting Cycle Bowhead’s long-term growth strategy balances existing “craft” underwriting model with “digital” business launched in 2024 Craft Digital Bowhead Express Baleen Specialty Strategy Custom underwriting of large, complicated risks Streamlined underwriting of small and medium business risks Restrictive coverage for hard-to-place small and medium business risks Underwriting Bespoke and collaborative Technology-aided workflow with light-touch Technology-driven Current Scope Casualty, Healthcare, & Professional Lines Cyber, MPL, Environmental (CPP), Primary Casualty (coming in Q2 2026) GL for Construction and Real Estate Differentiators Expertise-driven, customized approach for each risk Individualized underwriting with collaborative roundtables Maintain 100% control of underwriting; no delegated authority Set clear appetite and rules criteria during product development Straight-through processing delivers instant quotes, plus low-touch capabilities Distribution Wholesale & Retail channels Wholesale only Wholesale only Paper Admitted and Non-Admitted Non-Admitted only Non-Admitted only Operational Metrics Submission Volume High (hundreds per week) Very High (thousands per week) Very High (thousands per week) Quote Speed Hours-to-days Minutes Minutes

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 15 Well-Positioned to Manage Underwriting Cycle Having both “craft” and “digital” underwriting models creates flexibility to manage growth and profitability through underwriting cycles Leverage industry relationships to grow in attractive lines Pull back in softening lines while leaning into disrupted lines Add new distribution relationships Expand account size and/or geographic appetite as market allows Enter new lines/ markets by hiring subject matter experts Develop new products within existing lines

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 17 As of As of As of ($ in thousands) March 31, 2026 December 31, 2025 December 31, 2024 Fixed maturity securities $ 1,520,350 1,371,006 879,989 Short-term investments 4,976 — 9,997 Total investments $ 1,525,326 1,371,006 889,986 Cash and cash equivalents 97,185 193,545 97,476 Restricted cash and cash equivalents 44,343 40,225 124,582 Accrued investment income 11,327 10,958 7,520 Premium balances receivable 84,631 84,415 63,672 Reinsurance recoverable 433,265 399,676 255,072 Prepaid reinsurance premiums 192,110 191,821 152,567 Deferred policy acquisition costs 40,044 35,284 27,625 Property and equipment, net 11,307 10,636 6,845 Income taxes receivable 1,426 3,073 586 Deferred tax assets, net 27,742 22,476 20,340 Other assets 10,587 8,261 7,971 Total assets $ 2,479,293 2,371,376 1,654,242 Reserves for losses and loss expenses $ 1,220,800 1,129,936 756,859 Unearned premiums 556,416 552,594 446,850 Reinsurance balances payable 59,085 65,778 51,856 Debt 146,515 146,447 — Income taxes payable 6,213 314 1,571 Accrued expenses 11,088 19,047 18,010 Other liabilities 20,016 7,986 8,654 Total liabilities $ 2,020,133 1,922,102 1,283,800 Total mezzanine and stockholders' equity $ 459,160 449,274 370,442 Total liabilities and stockholders' equity $ 2,479,293 2,371,376 1,654,242 Summary Historical Financials Condensed Income Statement Condensed Balance Sheet ($ in thousands, except percentages and per share data) For the years ended Three months ended Revenues: December 31, 2025 December 31, 2024 March 31, 2026 March 31, 2025 Gross written premiums $ 862,806 695,717 216,741 174,848 Net written premiums 558,187 451,422 140,342 116,769 Net earned premiums 491,677 385,111 136,808 109,816 Net investment income 57,827 40,121 18,027 12,559 Total revenue $ 551,589 425,660 155,694 122,716 Net losses and loss adjustment expenses $ 328,022 248,099 91,481 73,427 Net acquisition costs 46,513 32,397 13,893 9,796 Operating expenses 102,264 89,112 25,804 23,937 Non-operating expenses 1,425 2,807 — 110 Warrant expense 3,142 1,917 775 775 Credit facility interest expenses and fees 2,012 725 3,162 247 Loss on extinguishment on credit facility 862 — — — Foreign exchange (gains) losses 50 68 8 (46) Total expenses $ 484,290 375,125 135,123 108,246 Net income $ 53,786 38,243 16,010 11,425 Key Operating and Financial Metrics     Underwriting Income1 $ 14,878 18,236 5,630 2,656 Adjusted net income1 $ 55,598 42,686 16,033 11,479 Loss ratio 66.7 % 64.4 % 66.9 % 66.9 % Expense ratio 29.8 % 31.4 % 28.4 % 30.4 % Combined ratio 96.5 % 95.8 % 95.3 % 97.3 % Return on equity2 13.1 % 13.6 % 14.1 % 12.0 % Adjusted return on equity1,2 13.6 % 15.2 % 14.1 % 12.1 % Diluted earnings per share $ 1.59 1.29 0.48 0.34 Diluted adjusted earnings per share1 $ 1.65 1.44 0.48 0.34 Notes: 1 Non-GAAP financial measure. See “Non-GAAP Reconciliation” on slide 20 for a reconciliation of the non-GAAP financial measures to their most directly comparable U.S. GAAP measures; 2 For the three months ended March 31, 2026 and 2025, net income and adjusted net income are annualized to arrive at return on equity and adjusted return on equity.

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 19 Long-term strategic partnership established at inception AmFam participates in underwriting results and generates fee-based earnings Policies backed by “A” rated paper with a "Standing the Test of Time" company distinction1 Our Partnership with AmFam Note: 1 American Family has a "Standing the Test of Time" company distinction, which is represented by having an AM Best financial strength rating of ‘A’ or better for at least 75 years. ☑ ☑☑ • Originates, issues, and underwrites all Bowhead policies • Provides all claims, actuarial, accounting, reinsurance procurement/processing and other insurance support services • Provides “A” rated paper for business originated by Bowhead • Receives ceding fee • Key agreements with AmFam include 100% Quote Share Agreement and MGA agreements • Assumes 100% of Bowhead policies from AmFam • Purchases reinsurance from high quality reinsurers (including AmFam) Bowhead has operational control over the entire policy lifecycle from distribution through claims management

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 20 Non-GAAP Reconciliation For the years ended Three months ended ($ in thousands, except percentages) December 31, 2025 December 31, 2024 March 31, 2026 March 31, 2025 Adjusted net income2 $ 55,598 42,686 64,135 45,916 Average mezzanine and stockholder’s equity 409,858 281,259 454,218 380,903 Adjusted return on equity 13.6 % 15.2 % 14.1 % 12.1 % For the years ended Three months ended ($ in thousands) December 31, 2025 December 31, 2024 March 31, 2026 March 31, 2025 Pre-Tax After- Tax Pre-Tax After- Tax Pre-Tax After- Tax Pre-Tax After- Tax Income as reported $ 67,299 53,786 50,535 38,243 20,571 16,010 14,470 11,425 Adjustments: Net realized investment losses (gains) (43) (43) 16 16 21 21 4 4 Non-operating expenses 1,425 1,425 2,807 2,807 — — 110 110 Loss on extinguishment of credit facility 862 862 — — — — — — Foreign exchange losses (gains) 50 50 68 68 8 8 (46) (46) Strategic initiatives1 — — 2,733 2,733 — — — — Tax impact — (482) — (1,181) — (6) — (14) Adjusted net income $ 69,593 55,598 56,159 42,686 20,600 16,033 14,538 11,479 For the years ended Three months ended ($ in thousands) December 31, 2025 December 31, 2024 March 31, 2026 March 31, 2025 Income before income taxes $ 67,299 50,535 20,571 14,470 Adjustments: Net investment income (57,827) (40,121) (18,027) (12,559) Net realized investment losses (gains) (43) 16 21 4 Other insurance-related income (2,042) (444) (880) (345) Non-operating expenses 1,425 2,807 — 110 Warrant expense 3,142 1,917 775 775 Credit facility interest expenses and fees 2,012 725 3,162 247 Loss on extinguishment of credit facility 862 — — — Foreign exchange losses (gains) 50 68 8 (46) Strategic initiatives1 — 2,733 — — Underwriting income $ 14,878 18,236 5,630 2,656 Note: 1 Strategic initiatives represents costs incurred to set up our Baleen Specialty division, which is recorded in operating expenses within the Condensed Income Statement. The costs incurred primarily represent expenses to implement the new platform and processes supporting the Baleen Specialty division; 2 For the three months ended March 31, 2026 and 2025, adjusted net income is annualized to arrive at adjusted return on equity. For the years ended Three months ended ($ in thousands, except per share data) December 31, 2025 December 31, 2024 March 31, 2026 March 31, 2025 Adjusted net income $ 55,598 42,686 16,033 11,479 Diluted weighted average shares outstanding 33,735,944 29,677,196 33,283,727 33,711,924 Diluted adjusted earnings per share $ 1.65 1.44 0.48 0.34