Hamilton Insurance Group, Ltd. Supplementary Financial Information September 30, 2025 Investor Contact Investor.Relations@hamiltongroup.com

Hamilton Insurance Group, Ltd. Table of Contents Page I. Basis of Presentation ......................................................................................................................................................................................................... 1 II. Financial Highlights Financial Highlights ............................................................................................................................................................................................................... 4 Key Operating and Financial Metrics ................................................................................................................................................................................. 5 III. Summary Consolidated Results Statements of Operations ................................................................................................................................................................................................... 6 Consolidated Balance Sheets ............................................................................................................................................................................................. 7 Reconciliation of Consolidated GAAP Balance Sheet to Unconsolidated Balance Sheet ....................................................................................... 8 Net Investment Return ......................................................................................................................................................................................................... 9 Fixed Maturity and Short-Term Investments ..................................................................................................................................................................... 10 IV. Segment Results Consolidated Underwriting Results .................................................................................................................................................................................... 11 5Q Consolidated Underwriting Results .............................................................................................................................................................................. 13 5Q Underwriting Results - International ............................................................................................................................................................................ 14 5Q Underwriting Results - Bermuda .................................................................................................................................................................................. 15 V. Other Information Modeled Exposure to Catastrophe Losses (PML) .......................................................................................................................................................... 16 Non-GAAP Measures ........................................................................................................................................................................................................... 17

1 Basis of Presentation All financial information contained herein is unaudited, however, certain information relating to the consolidated balance sheet at the most recent year end is derived from or agrees to audited financial information. Unless otherwise noted, all data is in thousands, except for share and per share amounts and ratio information. This information is being provided for informational purposes only. It should be read in conjunction with the documents filed by Hamilton Insurance Group, Ltd. (referred to herein as "Hamilton," the "Company," "we," "us" and "our") with the U.S. Securities and Exchange Commission, including its Form 10-Q. Special Note Regarding Forward-Looking Statements This information includes “forward looking statements” pursuant to the safe harbor provisions of the U.S. Private Securities Litigation Reform Act of 1995. Forward-looking statements can be identified by the use of terms such as “believes,” “expects,” “may,” “will,” “target,” “should,” “could,” “would,” “seeks,” “intends,” “plans,” “contemplates,” “estimates,” or “anticipates,” or similar expressions which concern our strategy, plans, projections or intentions. These forward-looking statements appear in a number of places throughout and relate to matters such as our industry, growth strategy, goals and expectations concerning our market position, future operations, margins, profitability, capital expenditures, liquidity and capital resources and other financial and operating information. By their nature, forward-looking statements: speak only as of the date they are made; are not statements of historical fact or guarantees of future performance; and are subject to risks, uncertainties, assumptions, or changes in circumstances that are difficult to predict or quantify. Our expectations, beliefs, and projections are expressed in good faith and we believe there is a reasonable basis for them. However, there can be no assurance that management’s expectations, beliefs and projections will be achieved and actual results may vary materially from what is expressed in or indicated by the forward-looking statements. There are a number of risks, uncertainties, and other important factors that could cause our actual results to differ materially from the forward-looking statements contained herein. Such risks, uncertainties, and other important factors include, among others, the risks, uncertainties and factors set forth in “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” included in the Company's Annual Report on Form 10-K for the year ended December 31, 2024 and other subsequent periodic reports filed with the Securities and Exchange Commission and the following: • challenges from competitors, including those arising from industry consolidation and technological advancements; • unpredictable catastrophic events, global climate change and/or emerging claim and coverage issues; • our ability, or those of the third parties on which we rely, to ensure reserves are adequate to cover actual losses and to accurately evaluate underwriting risk, models, assessments and/or pricing of risks; • our ability to defend our intellectual property rights, including our proprietary technology platforms, to comply with our obligations under our license and technology agreements or to license rights to technology or data on reasonable terms; • the impact of risks associated with human error, fraud, model uncertainties, cybersecurity threats such as cyber-attacks and security breaches and our reliance on third-party information technology ("IT") systems that can fail or need replacement; • our ability to secure necessary credit facilities, or additional types of credit, on favorable terms or at all; • our limited financial and operating flexibility due to the covenants in our existing credit facilities; • our exposure to the credit risk of the intermediaries on which we rely; • our failure to pay claims in a timely manner or the need to sell investments under unfavorable conditions to meet liquidity requirements;

2 Basis of Presentation Special Note Regarding Forward-Looking Statements (continued) • downgrades, potential downgrades or other negative actions by rating agencies; • our ability to manage risks associated with macroeconomic conditions resulting from geopolitical and global economic events, including current or anticipated military conflicts, public health crises, terrorism, sanctions, rising energy prices, inflation and interest rates and other global events, including the instability from recent international trade policies; • the cyclical nature of the insurance and reinsurance business, which may cause the pricing and terms for our products to decline; • our results of operations potentially fluctuating significantly from period to period and not being indicative of our long-term prospects; • our ability to execute our strategy and to modify our business and strategic plan without shareholder approval; • our dependence on key executives, including the potential loss of Bermudian personnel, and our ability to attract qualified personnel, particularly in very competitive hiring conditions; • foreign operational risk such as foreign currency risk and political risk; • our ability to identify and execute opportunities for growth, to complete transactions as planned or realize the anticipated benefits of any acquisitions or other investments; • our management of alternative reinsurance platforms on behalf of investors in entities managed by Hamilton Strategic Partnerships; • our inability to control the allocations to, and/or the performance of, the Two Sigma Hamilton Fund, LLC (“TS Hamilton Fund” or "Two Sigma Hamilton Fund") investment portfolio and our limited ability to withdraw our capital accounts; • the impact of risks from conflicts of interest among Two Sigma Principals, LLC, Two Sigma Investments, LP (“Two Sigma”) and their respective affiliates affecting our business; • the historical performance of Two Sigma not being indicative of the future results of the TS Hamilton Fund’s investment portfolio and/or of our future results; • the impacts of risks associated with our investment strategy, including that such risks are greater than those faced by our competitors; • our potentially becoming subject to U.S. federal income taxation, Bermuda taxation or other taxes as a result of a change of tax laws or otherwise; • the potential characterization of us and/or any of our subsidiaries as a passive foreign investment company, or PFIC; • our potentially becoming subject to U.S. withholding and information reporting requirements under the U.S. Foreign Account Tax Compliance Act, or FATCA, provisions; • our ability to compete effectively in a heavily regulated industry in light of new domestic or international laws and regulations, including accounting practices, and the impact of new interpretations of current laws and regulations; • the suspension or revocation of our subsidiaries’ insurance licenses; • significant legal, governmental or regulatory proceedings; • our insurance and reinsurance subsidiaries’ ability to pay dividends and other distributions to us being restricted by law; • challenges related to compliance with the applicable laws, rules and regulations related to being a public company, which is expensive and time consuming; • the limited ability of investors to influence corporate matters due to our multiple class common share structure and the voting provisions of our Bye-laws; • the risk that anti-takeover provisions in our Bye-laws could discourage, delay, or prevent a change in control, even if the change in control would be beneficial to our shareholders; • the difficulties investors may face in protecting their interests and serving process or enforcing judgments against us in the United States; and • our current strategy does not include paying cash dividends on our Class B common shares in the near term.

3 Basis of Presentation Special Note Regarding Forward-Looking Statements (continued) There may be other factors that could cause our actual results to differ materially from the forward-looking statements, including factors disclosed under the sections entitled “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” in the Form 10-K and other subsequent periodic reports filed with the Securities and Exchange Commission. You should evaluate all forward-looking statements made herein in the context of these risks and uncertainties. You should read this information completely and with the understanding that actual future results may be materially different from expectations. We caution you that the risks, uncertainties, and other factors referenced above may not contain all of the risks, uncertainties and other factors that are important to you. In addition, we cannot assure you that we will realize the results, benefits, or developments that we expect or anticipate or, even if substantially realized, that they will result in the consequences or affect us or our business in the way expected. All forward-looking statements contained herein apply only as of the date hereof and are expressly qualified in their entirety by these cautionary statements. We undertake no obligation to publicly update or revise any forward-looking statements to reflect subsequent events or circumstances.

4 Financial Highlights Three Months Ended September 30, Nine Months Ended September 30, Year Ended ($ in thousands) 2025 2024 2025 2024 2024 Net income (loss) attributable to common shareholders ........................................................ $ 136,200 $ 78,250 $ 404,486 $ 366,509 $ 400,429 Operating income (loss) attributable to common shareholders ............................................ $ 123,080 $ 16,551 $ 334,272 $ 327,670 $ 414,591 Underwriting income (loss) Gross premiums written ............................................................................................................... $ 698,845 $ 553,401 $ 2,254,177 $ 1,878,645 $ 2,422,582 Net premiums written ................................................................................................................... 578,981 477,896 1,739,169 1,467,843 1,921,169 Net premiums earned .................................................................................................................. 522,999 448,795 1,533,090 1,252,862 1,734,729 Underwriting income (loss) .......................................................................................................... $ 64,089 $ 29,094 $ 73,288 $ 126,920 $ 149,364 Key Ratios: Attritional loss ratio - current year .............................................................................................. 55.4 % 53.2 % 53.4 % 53.9 % 53.1 % Attritional loss ratio - prior year development ........................................................................... (2.1) % (0.7) % (1.8) % 0.6 % 0.0 % Catastrophe loss ratio - current year ......................................................................................... 0.0 % 11.5 % 11.1 % 4.1 % 6.3 % Catastrophe loss ratio - prior year development ...................................................................... 0.0 % (3.0) % (1.1) % (1.1) % (1.2) % Loss and loss adjustment expense ratio ................................................................................... 53.3 % 61.0 % 61.6 % 57.5 % 58.2 % Acquisition cost ratio .................................................................................................................... 24.0 % 22.8 % 23.8 % 22.6 % 22.4 % Other underwriting expense ratio ............................................................................................... 10.5 % 9.8 % 9.8 % 9.8 % 10.7 % Combined ratio .............................................................................................................................. 87.8 % 93.6 % 95.2 % 89.9 % 91.3 % Investments Total assets .................................................................................................................................... $ 9,213,370 $ 7,826,547 $ 9,213,370 $ 7,826,547 $ 7,796,033 Total cash and invested assets(1) ............................................................................................... 5,670,829 4,618,287 5,670,829 4,618,287 4,773,236 Total investment return(2) ............................................................................................................. 97,638 82,773 413,695 326,278 361,945 Two Sigma Hamilton Fund Total net realized and unrealized gains (losses) on investments and net investment income (loss) - TSHF ................................................................................................................... 94,469 (28,291) 465,888 379,712 487,186 Net income (loss) attributable to non-controlling interest - TSHF ......................................... 40,225 (17,215) 220,990 172,240 212,729 $ 54,244 $ (11,076) $ 244,898 $ 207,472 $ 274,457 Two Sigma Hamilton Fund return, net of investment management fees and performance incentive allocations .............................................................................................. 2.6 % (0.6) % 13.0 % 12.2 % 16.3 % Fixed income, short term investments and cash and cash equivalents Total net realized and unrealized gains (losses) on investments and net investment income (loss) - other .................................................................................................................... $ 43,394 $ 93,849 $ 168,797 $ 118,806 $ 87,488 (1) Total cash and total investments, plus receivables for investments sold, less payables for investments purchased, payables to related parties (TSHF) and non-controlling interest (TSHF). (2) Net realized and unrealized gains (losses) on investments, plus net investment income (loss), less non-controlling interest.

5 Three Months Ended September 30, Nine Months Ended September 30, Year Ended ($ in thousands, except per share amounts) 2025 2024 2025 2024 2024 Income (loss) per share attributable to common shareholders - basic ............................ $ 1.37 $ 0.77 $ 4.01 $ 3.45 $ 3.81 Income (loss) per share attributable to common shareholders - diluted .......................... $ 1.32 $ 0.74 $ 3.88 $ 3.33 $ 3.67 Operating income (loss) attributable to common shareholders per common share - diluted ......................................................................................................................................... $ 1.20 $ 0.16 $ 3.20 $ 2.97 $ 3.80 Weighted average common shares outstanding - basic ..................................................... 99,235,535 101,934,412 100,855,910 106,239,708 105,133,370 Weighted average common shares outstanding - diluted .................................................. 102,904,248 106,359,252 104,307,599 110,226,044 109,101,714 Return on average common shareholders' equity - annualized ........................................ 20.9 % 13.8 % 21.6 % 22.4 % 18.3 % Operating return on average common shareholders' equity - annualized ....................... 18.9 % 2.9 % 17.9 % 20.0 % 18.9 % September 30, 2025 December 31, 2024 Closing common shareholders' equity, less intangible assets ........................................... $ 2,573,145 $ 2,235,588 Closing common shareholders' equity ................................................................................... $ 2,661,993 $ 2,328,709 Closing common shares outstanding ..................................................................................... 98,361,499 101,466,997 Tangible book value per common share ............................................................................... $ 26.16 $ 22.03 Book value per common share ............................................................................................... $ 27.06 $ 22.95 Year to date change in tangible book value per common share ....................................... 18.7 % 24.1 % Year to date change in book value per common share ...................................................... 17.9 % 23.5 % Financial Highlights Key Operating and Financial Metrics

6 Three Months Ended September 30, Nine Months Ended September 30, Year Ended ($ in thousands, except per share amounts) 2025 2024 2025 2024 2024 Revenues Gross premiums written ............................................................................................................... $ 698,845 $ 553,401 $ 2,254,177 $ 1,878,645 $ 2,422,582 Reinsurance premiums ceded .................................................................................................... (119,864) (75,505) (515,008) (410,802) (501,413) Net premiums written ................................................................................................................... 578,981 477,896 1,739,169 1,467,843 1,921,169 Net change in unearned premiums ............................................................................................ (55,982) (29,101) (206,079) (214,981) (186,440) Net premiums earned .................................................................................................................. 522,999 448,795 1,533,090 1,252,862 1,734,729 Net realized and unrealized gains (losses) on investments .................................................. 115,136 48,228 571,964 454,851 511,407 Net investment income (loss) ..................................................................................................... 22,727 17,330 62,721 43,667 63,267 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ................................................................................................................................. 137,863 65,558 634,685 498,518 574,674 Third party fee income ................................................................................................................. 4,169 4,464 13,845 17,934 23,752 Net foreign exchange gains (losses) ......................................................................................... 2,619 (5,973) (4,422) (9,883) (3,231) Total revenues ............................................................................................................................. 667,650 512,844 2,177,198 1,759,431 2,329,924 Expenses Losses and loss adjustment expenses ..................................................................................... 278,712 273,632 943,875 720,478 1,010,173 Acquisition costs ........................................................................................................................... 125,412 102,201 365,108 283,059 388,931 Other underwriting expenses ...................................................................................................... 58,955 48,332 164,664 140,339 210,013 Corporate expenses ..................................................................................................................... 15,347 14,060 41,168 41,825 61,111 Amortization of intangible assets ............................................................................................... 4,000 5,204 11,895 11,773 15,520 Interest expense ........................................................................................................................... 4,933 5,351 15,264 17,090 22,616 Total expenses ............................................................................................................................ 487,359 448,780 1,541,974 1,214,564 1,708,364 Income (loss) before income tax ................................................................................................ 180,291 64,064 635,224 544,867 621,560 Income tax expense (benefit) ..................................................................................................... 3,866 3,029 9,748 6,118 8,402 Net income (loss) ........................................................................................................................ 176,425 61,035 625,476 538,749 613,158 Net income (loss) attributable to non-controlling interest ....................................................... 40,225 (17,215) 220,990 172,240 212,729 Net income (loss) and other comprehensive income (loss) attributable to common shareholders .............................................................................................................. $ 136,200 $ 78,250 $ 404,486 $ 366,509 $ 400,429 Per share data Income (loss) per share attributable to common shareholders - basic ................................ $ 1.37 $ 0.77 $ 4.01 $ 3.45 $ 3.81 Income (loss) per share attributable to common shareholders - diluted .............................. $ 1.32 $ 0.74 $ 3.88 $ 3.33 $ 3.67 Return on average common shareholders' equity - annualized ............................................ 20.9 % 13.8 % 21.6 % 22.4 % 18.3 % Summary Consolidated Results Statements of Operations

7 September 30, June 30, March 31, December 31, September 30, ($ in thousands, except share information) 2025 2025 2025 2024 2024 Assets Fixed maturity investments, at fair value (amortized cost September 30, 2025: $2,997,143) ...................................... $ 3,022,441 $ 2,698,470 $ 2,425,986 $ 2,377,862 $ 2,320,184 Short-term investments, at fair value (amortized cost September 30, 2025: $248,406) ............................................... 248,847 307,129 406,207 497,110 507,947 Investments in Two Sigma Funds, at fair value (cost September 30, 2025: $1,288,616) ............................................. 1,500,672 1,453,781 1,341,079 939,381 932,787 Total investments ....................................................................................................................................................................... 4,771,960 4,459,380 4,173,272 3,814,353 3,760,918 Cash and cash equivalents ...................................................................................................................................................... 955,130 985,649 838,514 996,493 957,372 Restricted cash and cash equivalents ................................................................................................................................... 110,087 85,648 74,548 104,359 93,883 Premiums receivable ................................................................................................................................................................ 1,012,000 1,048,580 989,656 771,707 885,744 Paid losses recoverable ........................................................................................................................................................... 115,847 131,833 91,701 134,406 146,008 Deferred acquisition costs ........................................................................................................................................................ 259,260 253,402 242,346 208,985 205,953 Unpaid losses and loss adjustment expenses recoverable ................................................................................................ 1,303,833 1,236,660 1,235,045 1,171,040 1,190,465 Receivables for investments sold ........................................................................................................................................... 45,182 38,271 46,358 74,006 39,079 Prepaid reinsurance .................................................................................................................................................................. 334,025 360,890 329,213 218,921 260,174 Intangible assets ........................................................................................................................................................................ 88,848 90,061 91,184 93,121 94,441 Other assets ............................................................................................................................................................................... 217,198 222,676 230,994 208,642 192,510 Total assets .............................................................................................................................................................................. $ 9,213,370 $ 8,913,050 $ 8,342,831 $ 7,796,033 $ 7,826,547 Liabilities, non-controlling interest, and shareholders' equity Liabilities Reserve for losses and loss adjustment expenses .............................................................................................................. $ 4,206,077 $ 3,984,281 $ 3,815,307 $ 3,532,491 $ 3,434,800 Unearned premiums ................................................................................................................................................................. 1,443,460 1,414,344 1,337,516 1,122,277 1,192,071 Reinsurance balances payable ............................................................................................................................................... 372,711 417,251 346,240 261,275 334,511 Payables for investments purchased ..................................................................................................................................... 102,013 127,529 46,925 115,427 172,905 Term loan, net of issuance costs ............................................................................................................................................ 149,717 149,691 149,974 149,945 149,916 Accounts payable and accrued expenses ............................................................................................................................. 167,882 141,838 137,667 185,361 168,658 Payables to related parties ...................................................................................................................................................... 28,338 50,233 70,709 100,420 — Total liabilities .......................................................................................................................................................................... 6,470,198 6,285,167 5,904,338 5,467,196 5,452,861 Non-controlling interest - TS Hamilton Fund ................................................................................................................... 81,179 69,292 39,154 128 60,060 Shareholders' equity Common shares: Class A, authorized (September 30, 2025: 26,944,807), par value $0.01; issued and outstanding (September 30, 2025: 17,820,078) .............................................................................................................................................................. 178 178 178 178 178 Class B, authorized (September 30, 2025: 83,577,932), par value $0.01; issued and outstanding (September 30, 2025: 64,537,772) .............................................................................................................................................................. 645 663 660 643 637 Class C, authorized (September 30, 2025: 16,003,649), par value $0.01; issued and outstanding (September 30, 2025: 16,003,649) .............................................................................................................................................................. 160 160 179 194 199 Additional paid-in-capital .......................................................................................................................................................... 1,135,815 1,148,571 1,160,569 1,163,609 1,172,331 Accumulated other comprehensive loss ................................................................................................................................ (4,441) (4,441) (4,441) (4,441) (4,441) Retained earnings ..................................................................................................................................................................... 1,529,636 1,413,460 1,242,194 1,168,526 1,144,722 Total shareholders' equity .................................................................................................................................................... 2,661,993 2,558,591 2,399,339 2,328,709 2,313,626 Total liabilities, non-controlling interest, and shareholders' equity ......................................................................... $ 9,213,370 $ 8,913,050 $ 8,342,831 $ 7,796,033 $ 7,826,547 Summary Consolidated Results Consolidated Balance Sheets

8 September 30, 2025 ($ in thousands) Consolidated GAAP Balance Sheet Two Sigma Hamilton Fund Balances Unconsolidated Balance Sheet(1) Assets Fixed maturity investments, at fair value .................................................................................................................................................................................... $ 3,022,441 $ - $ 3,022,441 Short-term investments, at fair value ......................................................................................................................................................................................... 248,847 (244,613) 4,234 Investments in Two Sigma Funds, at fair value ........................................................................................................................................................................ 1,500,672 621,519 2,122,191 Total investments ............................................................................................................................................................................................................................ 4,771,960 376,906 5,148,866 Cash and cash equivalents .......................................................................................................................................................................................................... 955,130 (536,457) 418,673 Restricted cash and cash equivalents ........................................................................................................................................................................................ 110,087 - 110,087 Premiums receivable ..................................................................................................................................................................................................................... 1,012,000 - 1,012,000 Paid losses recoverable ................................................................................................................................................................................................................ 115,847 - 115,847 Deferred acquisition costs ............................................................................................................................................................................................................ 259,260 - 259,260 Unpaid losses and loss adjustment expenses recoverable .................................................................................................................................................... 1,303,833 - 1,303,833 Receivables for investments sold ................................................................................................................................................................................................ 45,182 (40,760) 4,422 Prepaid reinsurance ....................................................................................................................................................................................................................... 334,025 - 334,025 Intangible assets ............................................................................................................................................................................................................................ 88,848 - 88,848 Other assets .................................................................................................................................................................................................................................... 217,198 (1,296) 215,902 Total assets ................................................................................................................................................................................................................................... $ 9,213,370 $ (201,607) $ 9,011,763 Liabilities, non-controlling interest, and shareholders' equity Liabilities Reserve for losses and loss adjustment expenses .................................................................................................................................................................. $ 4,206,077 $ - $ 4,206,077 Unearned premiums ...................................................................................................................................................................................................................... 1,443,460 - 1,443,460 Reinsurance balances payable .................................................................................................................................................................................................... 372,711 - 372,711 Payables for investments purchased .......................................................................................................................................................................................... 102,013 (91,876) 10,137 Term loan, net of issuance costs ................................................................................................................................................................................................. 149,717 - 149,717 Accounts payable and accrued expenses .................................................................................................................................................................................. 167,882 (214) 167,668 Payables to related parties ........................................................................................................................................................................................................... 28,338 (28,338) - Total liabilities ............................................................................................................................................................................................................................... 6,470,198 (120,428) 6,349,770 Non-controlling interest - TS Hamilton Fund ....................................................................................................................................................................... 81,179 (81,179) - Shareholders' equity Common shares: Class A, par value $0.01 ............................................................................................................................................................................................................... 178 - 178 Class B, par value $0.01 ............................................................................................................................................................................................................... 645 - 645 Class C, par value $0.01 ............................................................................................................................................................................................................... 160 - 160 Additional paid-in-capital ............................................................................................................................................................................................................... 1,135,815 - 1,135,815 Accumulated other comprehensive loss ..................................................................................................................................................................................... (4,441) - (4,441) Retained earnings .......................................................................................................................................................................................................................... 1,529,636 - 1,529,636 Total shareholders' equity ......................................................................................................................................................................................................... 2,661,993 - 2,661,993 Total liabilities, non-controlling interest, and shareholders' equity .............................................................................................................................. $ 9,213,370 $ (201,607) $ 9,011,763 Summary Consolidated Results Reconciliation of Consolidated GAAP Balance Sheet to Unconsolidated Balance Sheet (1) We present our balance sheet on an unconsolidated basis above, which we believe is meaningful and useful to investors, analysts, rating agencies and others who use our financial information to evaluate our performance. The unconsolidated balances are non-GAAP financial measures, with the above table providing an appropriate reconciliation to comparable GAAP measures.

9 Three Months Ended September 30, Nine Months Ended September 30, Year Ended ($ in thousands) 2025 2024 2025 2024 2024 Net realized gains (losses) on investments ............................................................ $ 109,355 $ 93,711 $ 424,142 $ 382,646 $ 468,068 Fixed maturities and short-term investments ............................................................ 3,274 2,769 4,140 (1,866) (2,307) TS Hamilton Fund ......................................................................................................... 106,081 90,942 420,002 384,228 470,091 Other................................................................................................................................ — — — 284 284 Change in net unrealized gains (losses) on investments ................................... 5,781 (45,483) 147,822 72,205 43,339 Fixed maturities and short-term investments ............................................................ 7,227 64,903 70,496 50,304 (8,908) TS Hamilton Fund ......................................................................................................... (1,446) (110,386) 77,326 21,901 52,247 Net realized and unrealized gains (losses) on investments .............................. 115,136 48,228 571,964 454,851 511,407 Net investment income (loss): Fixed maturities ................................................................................................................ 30,070 22,067 82,674 58,025 81,872 Short-term investments ................................................................................................... 155 10 453 50 67 TS Hamilton Fund ............................................................................................................ 3,243 3,108 7,837 9,040 12,373 Cash and cash equivalents ............................................................................................ 3,986 4,384 12,576 12,594 17,006 Other .................................................................................................................................. (575) 306 611 1,473 2,293 Interest and other .......................................................................................................... 36,879 29,875 104,151 81,182 113,611 Management fees ........................................................................................................... (13,889) (12,207) (40,574) (36,640) (49,102) Fixed maturities and short-term investments ............................................................ (636) (393) (1,837) (1,604) (2,192) TS Hamilton Fund ......................................................................................................... (13,253) (11,814) (38,737) (35,036) (46,910) Other expenses .............................................................................................................. (263) (338) (856) (875) (1,242) Fixed maturities and short-term investments ............................................................ (107) (197) (316) (455) (627) TS Hamilton Fund ......................................................................................................... (156) (141) (540) (421) (615) Net investment income (loss) ..................................................................................... 22,727 17,330 62,721 43,667 63,267 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ............................................................................................ 137,863 65,558 634,685 498,518 574,674 Net income (loss) attributable to non-controlling interest .......................................... 40,225 (17,215) 220,990 172,240 212,729 Total net realized and unrealized gains (losses) on investments and net investment income (loss), net of non-controlling interest ................................. $ 97,638 $ 82,773 $ 413,695 $ 326,278 $ 361,945 Fixed income, short-term investments and cash and cash equivalents return ...... $ 43,394 $ 93,849 $ 168,797 $ 118,806 $ 87,488 TS Hamilton Fund return(1) ............................................................................................. $ 54,244 $ (11,076) $ 244,898 $ 207,472 274,457 Summary Consolidated Results Net Investment Return (1) Net of non-controlling interest performance incentive allocation

10 September 30, 2025 December 31, 2024 ($ in thousands) Fair Value % of Total Weighted Average Credit Rating Fair Value % of Total Weighted Average Credit RatingFixed Maturity Trading Portfolio and Short-Term Investments(1) Fixed maturities U.S. government treasuries ...................................................................... $ 831,225 25% Aa1 $ 711,103 25% Aaa U.S. states, territories and municipalities ............................................... 12,890 0% Aa2 13,231 0% Aa2 Non-U.S. sovereign governments and supranationals ......................... 96,308 3% Aa1 67,527 2% Aa1 Corporate ..................................................................................................... 1,480,549 45% A3 1,143,060 41% A3 Residential mortgage-backed securities - Agency ................................ 363,002 11% Aa1 272,611 9% Aaa Residential mortgage-backed securities - Non-agency ....................... 33,759 1% Aaa 16,754 1% Aaa Commercial mortgage-backed securities - Non-agency ...................... 53,419 2% Aa1 39,686 1% Aaa Other asset-backed securities .................................................................. 151,289 5% Aa1 113,890 4% Aaa Total fixed maturities .................................................................................. 3,022,441 92% Aa3 2,377,862 83% Aa3 Short-term investments ................................................................................ 248,847 8% Aa1 497,110 17% Aaa Total fixed maturities and short-term investments ................................. $ 3,271,288 100% Aa3 $ 2,874,972 100% Aa2 Fixed Maturity and Short-Term Investments Credit Quality Summary Investment grade .......................................................................................... 100% 100% Non-investment grade .................................................................................. 0% 0% Total .............................................................................................................. 100% 100% Fixed Maturity and Short-Term Investments - Trading Portfolio(2) September 30, 2025 December 31, 2024 Average credit quality ................................................................................... Aa3 Aa3 Average yield to maturity ............................................................................. 4.1% 4.7% Book yield ....................................................................................................... 4.3% 4.1% Expected average duration (in years) ....................................................... 3.3 3.4 (1) Includes $244.6 million and $496.0 million of short-term investments, at September 30, 2025 and December 31, 2024, respectively, not managed by our external investment managers. (2) Fixed income portfolio managed by our external investment managers only. Summary Consolidated Results Fixed Maturity and Short-Term Investments

11 Three Months Ended September 30, 2025 Three Months Ended September 30, 2024 ($ in thousands) International Bermuda Total International Bermuda Total Gross premiums written ........................................................................ $ 379,957 $ 318,888 $ 698,845 $ 325,525 $ 227,876 $ 553,401 Net premiums written ............................................................................. 304,410 274,571 578,981 268,106 209,790 477,896 Net premiums earned ............................................................................ 252,302 270,697 522,999 225,244 223,551 448,795 Third party fee income ........................................................................... 2,137 2,032 4,169 4,170 294 4,464 Losses and loss adjustment expenses ............................................... 133,895 144,817 278,712 130,135 143,497 273,632 Acquisition costs ..................................................................................... 67,007 58,405 125,412 59,713 42,488 102,201 Other underwriting expenses ................................................................ 41,703 17,252 58,955 34,143 14,189 48,332 Underwriting income (loss) ................................................................... $ 11,834 $ 52,255 $ 64,089 $ 5,423 $ 23,671 $ 29,094 Key Ratios: Attritional loss ratio - current year ........................................................ 55.3 % 55.6 % 55.4 % 55.3 % 51.0 % 53.2 % Attritional loss ratio - prior year development .................................... (2.2) % (2.1) % (2.1) % (1.5) % 0.0 % (0.7) % Catastrophe loss ratio - current year ................................................... 0.0 % 0.0 % 0.0 % 6.4 % 16.7 % 11.5 % Catastrophe loss ratio - prior year development ............................... 0.0 % 0.0 % 0.0 % (2.4) % (3.5) % (3.0) % Loss and loss adjustment expense ratio ............................................ 53.1 % 53.5 % 53.3 % 57.8 % 64.2 % 61.0 % Acquisition cost ratio .............................................................................. 26.6 % 21.6 % 24.0 % 26.5 % 19.0 % 22.8 % Other underwriting expense ratio ......................................................... 15.7 % 5.6 % 10.5 % 13.3 % 6.2 % 9.8 % Combined ratio ........................................................................................ 95.4 % 80.7 % 87.8 % 97.6 % 89.4 % 93.6 % Segment Results Consolidated Underwriting Results

12 Nine Months Ended September 30, 2025 Nine Months Ended September 30, 2024 ($ in thousands) International Bermuda Total International Bermuda Total Gross premiums written ......................................................................... $ 1,094,715 $ 1,159,462 $ 2,254,177 $ 957,981 $ 920,664 $ 1,878,645 Net premiums written .............................................................................. 791,473 947,696 1,739,169 687,444 780,399 1,467,843 Net premiums earned ............................................................................. 746,078 787,012 1,533,090 637,700 615,162 1,252,862 Third party fee income ............................................................................ 10,301 3,544 13,845 11,557 6,377 17,934 Losses and loss adjustment expenses ................................................ 404,300 539,575 943,875 359,181 361,297 720,478 Acquisition costs ...................................................................................... 195,480 169,628 365,108 160,589 122,470 283,059 Other underwriting expenses ................................................................ 116,833 47,831 164,664 99,317 41,022 140,339 Underwriting income (loss) .................................................................... $ 39,766 $ 33,522 $ 73,288 $ 30,170 $ 96,750 $ 126,920 Key Ratios: Attritional loss ratio - current year ......................................................... 53.1 % 53.9 % 53.4 % 54.6 % 53.1 % 53.9 % Attritional loss ratio - prior year development ..................................... (2.9) % (0.8) % (1.8) % 0.3 % 0.8 % 0.6 % Catastrophe loss ratio - current year .................................................... 4.1 % 17.7 % 11.1 % 2.2 % 6.1 % 4.1 % Catastrophe loss ratio - prior year development ................................ (0.1) % (2.2) % (1.1) % (0.8) % (1.3) % (1.1) % Loss and loss adjustment expense ratio ............................................. 54.2 % 68.6 % 61.6 % 56.3 % 58.7 % 57.5 % Acquisition cost ratio ............................................................................... 26.2 % 21.6 % 23.8 % 25.2 % 19.9 % 22.6 % Other underwriting expense ratio ......................................................... 14.3 % 5.6 % 9.8 % 13.8 % 5.6 % 9.8 % Combined ratio ........................................................................................ 94.7 % 95.8 % 95.2 % 95.3 % 84.2 % 89.9 % Segment Results Consolidated Underwriting Results

13 Three Months Ended Nine Months Ended Year Ended September 30, June 30, March 31, December 31, September 30, September 30, September 30, December 31, ($ in thousands) 2025 2025 2025 2024 2024 2025 2024 2024 Gross premiums written ........................................... $ 698,845 $ 712,026 $ 843,306 $ 543,937 $ 553,401 $ 2,254,177 $ 1,878,645 $ 2,422,582 Net premiums written ................................................ 578,981 556,314 603,875 453,326 477,896 1,739,169 1,467,843 1,921,169 Net premiums earned ............................................... 522,999 511,163 498,928 481,867 448,795 1,533,090 1,252,862 1,734,729 Third party fee income .............................................. 4,169 5,014 4,662 5,818 4,464 13,845 17,934 23,752 Losses and loss adjustment expenses .................. 278,712 269,928 395,234 289,695 273,632 943,875 720,478 1,010,173 Acquisition costs ........................................................ 125,412 122,815 116,881 105,872 102,201 365,108 283,059 388,931 Other underwriting expenses .................................. 58,955 55,975 49,734 69,674 48,332 164,664 140,339 210,013 Underwriting income (loss) ...................................... $ 64,089 $ 67,459 $ (58,259) $ 22,444 $ 29,094 $ 73,288 $ 126,920 $ 149,364 Key Ratios: Attritional loss ratio - current year ........................... 55.4 % 53.0 % 51.9 % 51.2 % 53.2 % 53.4 % 53.9 % 53.1 % Attritional loss ratio - prior year development ....... (2.1) % (0.5) % (2.9) % (1.3) % (0.7) % (1.8) % 0.6 % 0.0 % Catastrophe loss ratio - current year ...................... 0.0 % 1.9 % 32.0 % 11.9 % 11.5 % 11.1 % 4.1 % 6.3 % Catastrophe loss ratio - prior year development .. 0.0 % (1.6) % (1.8) % (1.7) % (3.0) % (1.1) % (1.1) % (1.2) % Loss and loss adjustment expense ratio ............... 53.3 % 52.8 % 79.2 % 60.1 % 61.0 % 61.6 % 57.5 % 58.2 % Acquisition cost ratio ................................................. 24.0 % 24.0 % 23.4 % 22.0 % 22.8 % 23.8 % 22.6 % 22.4 % Other underwriting expense ratio ............................ 10.5 % 10.0 % 9.0 % 13.3 % 9.8 % 9.8 % 9.8 % 10.7 % Combined ratio .......................................................... 87.8 % 86.8 % 111.6 % 95.4 % 93.6 % 95.2 % 89.9 % 91.3 % Gross premiums written Property ...................................................................... $ 134,626 $ 207,488 $ 277,603 $ 77,378 $ 120,001 $ 619,717 $ 536,738 $ 614,116 Casualty ...................................................................... 377,483 322,446 315,097 298,607 272,998 1,015,025 780,517 1,079,124 Specialty ..................................................................... 186,736 182,092 250,606 167,952 160,402 619,435 561,390 729,342 Total .......................................................................... $ 698,845 $ 712,026 $ 843,306 $ 543,937 $ 553,401 $ 2,254,177 $ 1,878,645 $ 2,422,582 Net premiums earned Property ...................................................................... $ 130,248 $ 124,019 $ 141,173 $ 122,734 $ 121,766 $ 395,440 $ 335,028 $ 457,762 Casualty ...................................................................... 243,997 232,047 217,672 205,234 193,948 693,716 528,295 733,529 Specialty ..................................................................... 148,754 155,097 140,083 153,899 133,081 443,934 389,539 543,438 Total .......................................................................... $ 522,999 $ 511,163 $ 498,928 $ 481,867 $ 448,795 $ 1,533,090 $ 1,252,862 $ 1,734,729 Segment Results 5Q Consolidated Underwriting Results - Group

14 Three Months Ended Nine Months Ended Year Ended September 30, June 30, March 31, December 31, September 30, September 30, September 30, December 31, ($ in thousands) 2025 2025 2025 2024 2024 2025 2024 2024 Gross premiums written ........................................... $ 379,957 $ 344,799 $ 369,959 $ 350,479 $ 325,525 $ 1,094,715 $ 957,981 $ 1,308,460 Net premiums written ................................................ 304,410 258,089 228,975 282,161 268,106 791,473 687,444 969,605 Net premiums earned ............................................... 252,302 253,209 240,567 249,234 225,244 746,078 637,700 886,934 Third party fee income .............................................. 2,137 3,832 4,332 4,760 4,170 10,301 11,557 16,317 Losses and loss adjustment expenses .................. 133,895 124,733 145,671 138,842 130,135 404,300 359,181 498,023 Acquisition costs ........................................................ 67,007 65,683 62,790 56,382 59,713 195,480 160,589 216,971 Other underwriting expenses .................................. 41,703 39,507 35,623 49,507 34,143 116,833 99,317 148,824 Underwriting income (loss) ...................................... $ 11,834 $ 27,118 $ 815 $ 9,263 $ 5,423 $ 39,766 $ 30,170 $ 39,433 Key Ratios: Attritional loss ratio - current year ........................... 55.3 % 51.9 % 52.1 % 50.8 % 55.3 % 53.1 % 54.6 % 53.5 % Attritional loss ratio - prior year development ....... (2.2) % (3.0) % (3.6) % (2.1) % (1.5) % (2.9) % 0.3 % (0.4) % Catastrophe loss ratio - current year ...................... 0.0 % 0.6 % 12.1 % 7.8 % 6.4 % 4.1 % 2.2 % 3.9 % Catastrophe loss ratio - prior year development .. 0.0 % (0.2) % 0.0 % (0.8) % (2.4) % (0.1) % (0.8) % (0.8) % Loss and loss adjustment expense ratio ............... 53.1 % 49.3 % 60.6 % 55.7 % 57.8 % 54.2 % 56.3 % 56.2 % Acquisition cost ratio ................................................. 26.6 % 25.9 % 26.1 % 22.6 % 26.5 % 26.2 % 25.2 % 24.5 % Other underwriting expense ratio ............................ 15.7 % 14.1 % 13.0 % 18.0 % 13.3 % 14.3 % 13.8 % 14.9 % Combined ratio .......................................................... 95.4 % 89.3 % 99.7 % 96.3 % 97.6 % 94.7 % 95.3 % 95.6 % Gross premiums written Property ...................................................................... $ 63,894 $ 63,871 $ 54,526 $ 47,684 $ 51,441 $ 182,292 $ 142,685 $ 190,369 Casualty ...................................................................... 167,107 140,441 135,563 157,013 144,107 443,110 397,400 554,413 Specialty ..................................................................... 148,956 140,487 179,870 145,782 129,977 469,313 417,896 563,678 Total .......................................................................... $ 379,957 $ 344,799 $ 369,959 $ 350,479 $ 325,525 $ 1,094,715 $ 957,981 $ 1,308,460 Net premiums earned Property ...................................................................... $ 47,813 $ 43,706 $ 45,705 $ 44,621 $ 37,033 $ 137,223 $ 104,697 $ 149,318 Casualty ...................................................................... 91,841 89,233 90,568 84,776 86,062 271,643 234,760 319,536 Specialty ..................................................................... 112,648 120,270 104,294 119,837 102,149 337,212 298,243 418,080 Total .......................................................................... $ 252,302 $ 253,209 $ 240,567 $ 249,234 $ 225,244 $ 746,078 $ 637,700 $ 886,934 Segment Results 5Q Underwriting Results - International

15 Three Months Ended Nine Months Ended Year Ended September 30, June 30, March 31, December 31, September 30, September 30, September 30, December 31, ($ in thousands) 2025 2025 2025 2024 2024 2025 2024 2024 Gross premiums written ........................................... $ 318,888 $ 367,227 $ 473,347 $ 193,458 $ 227,876 $ 1,159,462 $ 920,664 $ 1,114,122 Net premiums written ................................................ 274,571 298,225 374,900 171,165 209,790 947,696 780,399 951,564 Net premiums earned ............................................... 270,697 257,954 258,361 232,633 223,551 787,012 615,162 847,795 Third party fee income .............................................. 2,032 1,182 330 1,058 294 3,544 6,377 7,435 Losses and loss adjustment expenses .................. 144,817 145,195 249,563 150,853 143,497 539,575 361,297 512,150 Acquisition costs ........................................................ 58,405 57,132 54,091 49,490 42,488 169,628 122,470 171,960 Other underwriting expenses .................................. 17,252 16,468 14,111 20,167 14,189 47,831 41,022 61,189 Underwriting income (loss) ...................................... $ 52,255 $ 40,341 $ (59,074) $ 13,181 $ 23,671 $ 33,522 $ 96,750 $ 109,931 Key Ratios: Attritional loss ratio - current year ........................... 55.6 % 54.2 % 51.8 % 51.7 % 51.0 % 53.9 % 53.1 % 52.7 % Attritional loss ratio - prior year development ....... (2.1) % 2.0 % (2.2) % (0.4) % 0.0 % (0.8) % 0.8 % 0.5 % Catastrophe loss ratio - current year ...................... 0.0 % 3.2 % 50.6 % 16.1 % 16.7 % 17.7 % 6.1 % 8.9 % Catastrophe loss ratio - prior year development .. 0.0 % (3.1) % (3.6) % (2.6) % (3.5) % (2.2) % (1.3) % (1.7) % Loss and loss adjustment expense ratio ............... 53.5 % 56.3 % 96.6 % 64.8 % 64.2 % 68.6 % 58.7 % 60.4 % Acquisition cost ratio ................................................. 21.6 % 22.1 % 20.9 % 21.3 % 19.0 % 21.6 % 19.9 % 20.3 % Other underwriting expense ratio ............................ 5.6 % 5.9 % 5.3 % 8.2 % 6.2 % 5.6 % 5.6 % 6.3 % Combined ratio .......................................................... 80.7 % 84.3 % 122.8 % 94.3 % 89.4 % 95.8 % 84.2 % 87.0 % Gross premiums written Property ...................................................................... $ 70,732 $ 143,617 $ 223,077 $ 29,694 $ 68,560 $ 437,425 $ 394,053 $ 423,747 Casualty ...................................................................... 210,376 182,005 179,534 141,594 128,891 571,915 383,117 524,711 Specialty ..................................................................... 37,780 41,605 70,736 22,170 30,425 150,122 143,494 165,664 Total .......................................................................... $ 318,888 $ 367,227 $ 473,347 $ 193,458 $ 227,876 $ 1,159,462 $ 920,664 $ 1,114,122 Net premiums earned Property ...................................................................... $ 82,435 $ 80,313 $ 95,468 $ 78,113 $ 84,733 $ 258,217 $ 230,331 $ 308,444 Casualty ...................................................................... 152,156 142,814 127,104 120,458 107,886 422,073 293,535 413,993 Specialty ..................................................................... 36,106 34,827 35,789 34,062 30,932 106,722 91,296 125,358 Total .......................................................................... $ 270,697 $ 257,954 $ 258,361 $ 232,633 $ 223,551 $ 787,012 $ 615,162 $ 847,795 Segment Results 5Q Underwriting Results - Bermuda

16 Region Peril Probability of Exceedance Group Net PML ($m)(1) % of Shareholders' Equity Florida U.S. Hurricane 1 in 100 $ 227.9 8.6 % Northeast U.S. Hurricane 1 in 100 210.6 7.9 % Gulf (TX - AL) U.S. Hurricane 1 in 100 179.1 6.7 % California Earthquake 1 in 250 289.2 10.9 % Pacific Northwest Earthquake 1 in 250 122.5 4.6 % (1) Group Net PML is a measure of loss across all Hamilton entities net of recoveries from various reinsurance contracts and catastrophe bonds we purchase to mitigate catastrophe losses and net of estimated reinstatement premium to renew coverage. Our peak natural catastrophe PMLs are derived using vendor catastrophe models that serve as a baseline and proprietary tools that allow us to make a number of significant adjustments. Adjustments are informed by periodic evaluation of vendor models and risk learning from comparing actual and modeled losses of catastrophe events, thus allowing for a view of risk that we believe is materially more complete and appropriate to the current risk landscape. Our peak natural catastrophe PMLs are measured using stochastic models that use hypothetical events of perils such as hurricanes and earthquakes. We define PML as the anticipated loss, taking into account contract terms and limits, caused by a single catastrophe affecting a broad contiguous geographical area, and are expressed at refine "return periods", such as "100-year events" and "250-year events". For example, a 100-year PML is the estimated loss to the current in-force portfolio from a single event which has a 1% probability of being exceeded in a twelve month period. Due to the uncertain nature of catastrophes and the hypothetical nature of vendor catastrophe models we use for estimating losses, there is no assurance that actual losses we experience within a time period will match the modeled PML. This approach to measuring catastrophe losses, however, is consistent with the best practice in the industry and employed by almost all of our peers. Other Information Modeled Exposure to Catastrophe Losses (PML) Net Probable Maximum Loss ("PML") as of October 1, 2025 ($ in millions)

17 Other Information Non-GAAP Measures We present our results of operations in a way that we believe will be the most meaningful and useful to investors, analysts, rating agencies and others who use our financial information to evaluate our performance. Some of the measurements that management uses to assess our operating results are considered non-GAAP financial measures under Regulation G and Item 10(e) of Regulation S-K, each promulgated by the SEC. We believe that these non- GAAP financial measures, which may be defined and calculated differently by other companies, help explain and enhance the understanding of our results of operations. However, these measures should not be viewed as a substitute for those determined in accordance with U.S. GAAP. Where appropriate, reconciliations of our non-GAAP measures to the most directly comparable GAAP financial measures are included below. Operating Income (Loss) Attributable to Common Shareholders, Operating Income (Loss) Attributable to Common Shareholders per Common Share - Diluted and Operating Return on Average Common Shareholders' Equity - Annualized Operating income (loss) attributable to common shareholders, as used herein, differs from net income (loss) and other comprehensive income (loss) attributable to common shareholders, which we believe is the most directly comparable GAAP measure, by the exclusion of net realized and unrealized gains and losses on fixed maturity and short term investments, and net foreign exchange gains and losses. We also use operating income (loss) attributable to common shareholders to calculate operating income (loss) attributable to common shareholders per common share - diluted and operating return on average common shareholders' equity - annualized. We believe that operating income (loss) attributable to common shareholders, operating income (loss) attributable to common shareholders per common share - diluted and operating return on average common shareholders' equity - annualized are meaningful and useful to investors, analysts, rating agencies and others who use our financial information to evaluate our performance. The following tables are a reconciliation of: net income (loss) and other comprehensive income (loss) attributable to common shareholders to operating income (loss) attributable to common shareholders; net income (loss) and other comprehensive income (loss) attributable to common shareholders per common share - diluted to operating income (loss) attributable to common shareholders per common share - diluted; and return on average common shareholders' equity - annualized to operating return on average common shareholders' equity - annualized. Comparative information for the prior periods presented have been updated to conform to the current methodology and presentation.

18 Return on average common shareholders' equity - annualized ................................................................................. 20.9 % 13.8 % 21.6 % 22.4 % Adjustment for: ................................................................................................................................................................... Net realized (gains) losses on investments - Fixed maturity and short-term investments(1) .................................. (0.5) % (0.5) % (0.2) % 0.1 % Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1) ............................. (1.1) % (11.4) % (3.7) % (3.1) % Net foreign exchange (gains) losses .............................................................................................................................. (0.4) % 1.0 % 0.2 % 0.6 % Operating return on average common shareholders' equity - annualized ................................................................ 18.9 % 2.9 % 17.9 % 20.0 % Other Information Non-GAAP Measures Net income (loss) and other comprehensive income (loss) attributable to common shareholders per common share - diluted .................................................................................................................................................... $ 1.32 $ 0.74 $ 3.88 $ 3.33 Adjustment for: ................................................................................................................................................................... Net realized (gains) losses on investments - Fixed maturity and short-term investments(1) .................................. (0.03) (0.03) (0.04) 0.01 Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1) ............................. (0.07) (0.61) (0.68) (0.46) Net foreign exchange (gains) losses .............................................................................................................................. (0.02) 0.06 0.04 0.09 Operating income (loss) attributable to common shareholders per common share - diluted ................................ $ 1.20 $ 0.16 $ 3.20 $ 2.97 Three Months Ended September 30, Nine Months Ended September 30, ($ in thousands) 2025 2024 2025 2024 Net income (loss) and other comprehensive income (loss) attributable to common shareholders ...................... $ 136,200 $ 78,250 $ 404,486 $ 366,509 Adjustment for: ................................................................................................................................................................... Net realized (gains) losses on investments - Fixed maturity and short-term investments(1) .................................. (3,274) (2,769) (4,140) 1,582 Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1) ............................. (7,227) (64,903) (70,496) (50,304) Net foreign exchange (gains) losses .............................................................................................................................. (2,619) 5,973 $ 4,422 $ 9,883 Operating income (loss) attributable to common shareholders .................................................................................. $ 123,080 $ 16,551 $ 334,272 $ 327,670 Operating Income (Loss) Attributable to Common Shareholders, Operating Income (Loss) Attributable to Common Shareholders per Common Share - Diluted and Operating Return on Average Common Shareholders' Equity - Annualized (continued) (1) Fixed income portfolio managed by our external investment managers only.

19 Underwriting Income (Loss) We calculate underwriting income (loss) on a pre-tax basis as net premiums earned less losses and loss adjustment expenses, acquisition costs and other underwriting expenses (net of third party fee income). We believe that this measure of our performance focuses on the core fundamental performance of the Company’s reportable segments in any given period and is not distorted by investment market conditions, corporate expense allocations or income tax effects. The table below reconciles underwriting income (loss) to net income (loss), the most directly comparable GAAP financial measure: Three Months Ended September 30, Nine Months Ended September 30, ($ in thousands) 2025 2024 2025 2024 Underwriting income (loss) ............................................................................................................................................... $ 64,089 $ 29,094 $ 73,288 $ 126,920 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ................... 137,863 65,558 634,685 498,518 Net foreign exchange gains (losses) .............................................................................................................................. 2,619 (5,973) (4,422) (9,883) Corporate expenses .......................................................................................................................................................... (15,347) (14,060) (41,168) (41,825) Amortization of intangible assets ..................................................................................................................................... (4,000) (5,204) (11,895) (11,773) Interest expense ................................................................................................................................................................. (4,933) (5,351) (15,264) (17,090) Income tax (expense) benefit ........................................................................................................................................... (3,866) (3,029) (9,748) (6,118) Net income (loss), prior to non-controlling interest ....................................................................................................... $ 176,425 $ 61,035 $ 625,476 $ 538,749 Other Information Non-GAAP Measures Third Party Fee Income Third party fee income includes income that is incremental and/or directly attributable to our underwriting operations. It is primarily comprised of fees earned by the International segment for management services provided to third party syndicates and consortia and by the Bermuda segment for performance based management fees generated by our third party capital manager, Ada Capital Management Limited. We believe that this measure is a relevant component of our underwriting income (loss), with other income (loss) being the most directly comparable GAAP financial measure. Three Months Ended September 30, Nine Months Ended September 30, ($ in thousands) 2025 2024 2025 2024 Third party fee income ...................................................................................................................................................... $ 4,169 $ 4,464 $ 13,845 $ 17,934 Other income (loss), excluding third party fee income ................................................................................................. — — — — Other income (loss) ........................................................................................................................................................... $ 4,169 $ 4,464 $ 13,845 $ 17,934

20 Three Months Ended September 30, Nine Months Ended September 30, ($ in thousands) 2025 2024 2025 2024 Other underwriting expenses ........................................................................................................................................... $ 58,955 $ 48,332 $ 164,664 $ 140,339 Corporate expenses .......................................................................................................................................................... 15,347 14,060 41,168 41,825 General and administrative expenses ............................................................................................................................ $ 74,302 $ 62,392 $ 205,832 $ 182,164 Other Information Non-GAAP Measures Other Underwriting Expenses Other underwriting expenses include those general and administrative expenses that are incremental and/or directly attributable to our underwriting operations. While this measure is presented in Note 8, Segment Reporting in the unaudited condensed consolidated financial statements, it is considered a non-GAAP financial measure when presented elsewhere. Corporate expenses include holding company costs necessary to support our reportable segments. As these costs are not incremental and/or directly attributable to our underwriting operations, these costs are excluded from other underwriting expenses, and therefore, underwriting income (loss). General and administrative expenses, the most comparable GAAP financial measure to other underwriting expenses, also includes corporate expenses. The table below reconciles other underwriting expenses to general and administrative expenses, the most directly comparable GAAP financial measure: Other Underwriting Expense Ratio Other Underwriting Expense Ratio is a measure of the other underwriting expenses (net of third party fee income) incurred by the Company and is expressed as a percentage of net premiums earned. Loss Ratio Attritional Loss Ratio – current year is the attritional losses incurred by the company relating to the current year divided by net premiums earned. Attritional Loss Ratio – prior year development is the attritional losses incurred by the company relating to prior years divided by net premiums earned. Catastrophe Loss Ratio – current year is the catastrophe losses incurred by the company relating to the current year divided by net premiums earned. Catastrophe Loss Ratio – prior year development is the catastrophe losses incurred by the company relating to prior years divided by net premiums earned. Combined Ratio Combined Ratio is a measure of our underwriting profitability and is expressed as the sum of the loss and loss adjustment expense ratio, acquisition cost ratio and other underwriting expense ratio. A combined ratio under 100% indicates an underwriting profit, while a combined ratio over 100% indicates an underwriting loss.

Investor Presentation Hamilton Insurance Group, Ltd. September 30, 2025

2 Special Note Regarding Forward-Looking Statements This information includes “forward looking statements” pursuant to the safe harbor provisions of the U.S. Private Securities Litigation Reform Act of 1995. Forward-looking statements can be identified by the use of terms such as “believes,” “expects,” “may,” “will,” “target,” “should,” “could,” “would,” “seeks,” “intends,” “plans,” “contemplates,” “estimates,” or “anticipates,” or similar expressions which concern our strategy, plans, projections or intentions. These forward-looking statements appear in a number of places throughout and relate to matters such as our industry, growth strategy, goals and expectations concerning our market position, future operations, margins, profitability, capital expenditures, liquidity and capital resources and other financial and operating information. By their nature, forward-looking statements: speak only as of the date they are made; are not statements of historical fact or guarantees of future performance; and are subject to risks, uncertainties, assumptions, or changes in circumstances that are difficult to predict or quantify. Our expectations, beliefs, and projections are expressed in good faith and we believe there is a reasonable basis for them. However, there can be no assurance that management’s expectations, beliefs and projections will be achieved and actual results may vary materially from what is expressed in or indicated by the forward-looking statements. There are a number of risks, uncertainties, and other important factors that could cause our actual results to differ materially from the forward-looking statements contained herein. Such risks, uncertainties, and other important factors include, among others, the risks, uncertainties and factors set forth in “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” included in the Company's Annual Report on Form 10-K for the year ended December 31, 2024 and other subsequent periodic reports filed with the Securities and Exchange Commission and the following: • challenges from competitors, including those arising from industry consolidation and technological advancements; • unpredictable catastrophic events, global climate change and/or emerging claim and coverage issues; • our ability, or those of the third parties on which we rely, to ensure reserves are adequate to cover actual losses and to accurately evaluate underwriting risk, models, assessments and/or pricing of risks; • our ability to defend our intellectual property rights, including our proprietary technology platforms, to comply with our obligations under our license and technology agreements or to license rights to technology or data on reasonable terms; • the impact of risks associated with human error, fraud, model uncertainties, cybersecurity threats such as cyber-attacks and security breaches and our reliance on third- party information technology ("IT") systems that can fail or need replacement; • our ability to secure necessary credit facilities, or additional types of credit, on favorable terms or at all; • our limited financial and operating flexibility due to the covenants in our existing credit facilities; • our exposure to the credit risk of the intermediaries on which we rely; • our failure to pay claims in a timely manner or the need to sell investments under unfavorable conditions to meet liquidity requirements; • downgrades, potential downgrades or other negative actions by rating agencies; • our ability to manage risks associated with macroeconomic conditions resulting from geopolitical and global economic events, including current or anticipated military conflicts, public health crises, terrorism, sanctions, rising energy prices, inflation and interest rates and other global events, including the instability from recent international trade policies; • the cyclical nature of the insurance and reinsurance business, which may cause the pricing and terms for our products to decline; • our results of operations potentially fluctuating significantly from period to period and not being indicative of our long-term prospects; • our ability to execute our strategy and to modify our business and strategic plan without shareholder approval; • our dependence on key executives, including the potential loss of Bermudian personnel, and our ability to attract qualified personnel, particularly in very competitive hiring conditions; • foreign operational risk such as foreign currency risk and political risk;

3 • our ability to identify and execute opportunities for growth, to complete transactions as planned or realize the anticipated benefits of any acquisitions or other investments; • our management of alternative reinsurance platforms on behalf of investors in entities managed by Hamilton Strategic Partnerships; • our inability to control the allocations to, and/or the performance of, the Two Sigma Hamilton Fund, LLC (“TS Hamilton Fund” or "Two Sigma Hamilton Fund") investment portfolio and our limited ability to withdraw our capital accounts; • the impact of risks from conflicts of interest among Two Sigma Principals, LLC, Two Sigma Investments, LP (“Two Sigma”) and their respective affiliates affecting our business; • the historical performance of Two Sigma not being indicative of the future results of the TS Hamilton Fund’s investment portfolio and/or of our future results; • the impacts of risks associated with our investment strategy, including that such risks are greater than those faced by our competitors; • our potentially becoming subject to U.S. federal income taxation, Bermuda taxation or other taxes as a result of a change of tax laws or otherwise; • the potential characterization of us and/or any of our subsidiaries as a passive foreign investment company, or PFIC; • our potentially becoming subject to U.S. withholding and information reporting requirements under the U.S. Foreign Account Tax Compliance Act, or FATCA, provisions; • our ability to compete effectively in a heavily regulated industry in light of new domestic or international laws and regulations, including accounting practices, and the impact of new interpretations of current laws and regulations; • the suspension or revocation of our subsidiaries’ insurance licenses; • significant legal, governmental or regulatory proceedings; • our insurance and reinsurance subsidiaries’ ability to pay dividends and other distributions to us being restricted by law; • challenges related to compliance with the applicable laws, rules and regulations related to being a public company, which is expensive and time consuming; • the limited ability of investors to influence corporate matters due to our multiple class common share structure and the voting provisions of our Bye-laws; • the risk that anti-takeover provisions in our Bye-laws could discourage, delay, or prevent a change in control, even if the change in control would be beneficial to our shareholders; • the difficulties investors may face in protecting their interests and serving process or enforcing judgments against us in the United States; and • our current strategy does not include paying cash dividends on our Class B common shares in the near term. There may be other factors that could cause our actual results to differ materially from the forward-looking statements, including factors disclosed under the sections entitled “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” in the Form 10-K and other subsequent periodic reports filed with the Securities and Exchange Commission. You should evaluate all forward-looking statements made herein in the context of these risks and uncertainties. You should read this information completely and with the understanding that actual future results may be materially different from expectations. We caution you that the risks, uncertainties, and other factors referenced above may not contain all of the risks, uncertainties and other factors that are important to you. In addition, we cannot assure you that we will realize the results, benefits, or developments that we expect or anticipate or, even if substantially realized, that they will result in the consequences or affect us or our business in the way expected. All forward-looking statements contained herein apply only as of the date hereof and are expressly qualified in their entirety by these cautionary statements. We undertake no obligation to publicly update or revise any forward-looking statements to reflect subsequent events or circumstances. Special Note Regarding Forward-Looking Statements, Continued

5 Highly Experienced Leadership Team Gemma Carreiro 20+ Years General Counsel Former: PartnerRe Pina Albo 30+ Years Group CEO Former: Munich Re Craig Howie 35+ Years Group CFO Former: Everest Anita Kuchma 35+ Years CEO, Hamilton Select Former: Munich Re Alex Baker 20+ Years CEO, Hamilton Global Specialty Former: Chubb Insurance Adrian Daws 20+ Years CEO, Hamilton Re Former: CNA Hardy Daniel Fisher 20+ Years Group Head of HR, Communications & Culture Former: Munich Re Executive Leadership Hamilton: In good company. Fostering an inclusive, collaborative and entrepreneurial culture Highly Collaborative Service Oriented Open, Diverse and Inclusive Expertise Experienced Board of Directors Russ Buckley 30+ Years Group Chief Risk Officer Former: Old Republic Raymond Karrenbauer 25+ Years Group CIO Former: Cyber AB

6 $2.4B FY 2024 $2.3B 9M 2025 Gross Premiums Written (“GPW”) $149m FY 2024 $73m 9M 2025 Underwriting Income 91.3% FY 2024 95.2% 9M 2025 Combined Ratio Hamilton – Overview and Results Annual Segmental Results Group Financial Highlights $5.7B 3Q 2025 Cash & Invested Assets $2.7B 3Q 2025 Shareholders’ Equity $400m FY 2024 $405m 9M 2025 Net Income R e p o rt in g S e g m e n ts International 2024 GPW $1.3B Bermuda 2024 GPW $1.1B Hamilton Global Specialty (London & Dublin) Hamilton Select (USA) Hamilton Re (Bermuda)O p e ra ti n g P la tf o rm s 20 24 S e g m e n t C o m b in e d R at io 95.6% 87.0% Financial Strength Ratings “A” (Stable) AM Best “A” (Stable) KBRA “A-” (Stable) Fitch AM Best and Fitch are ratings of Hamilton Re, Ltd. and Hamilton Insurance DAC. KBRA is the rating for Hamilton Re, Ltd.

7 Insurance 53% Reinsurance 47% Insurance / Reinsurance Casualty 45% Specialty 30% Property 25% Class of Business International 54% Bermuda 46% Business Segments 2024 Gross Premiums Written of $2.4 Billion Global Presence Bermuda Ireland United Kingdom United States Diversified and Well Scaled Underwriting Platforms Facilitate Cycle Management Diversified by Insurance / Reinsurance, Class of Business, and Segment / Geography

8 71% 68% 66% 54% 58% 58% 62% 40% 38% 37% 36% 33% 32% 34% 111% 106% 103% 90% 91% 90% 95% 2020 2021 2022 2023 2024 9M 2024 9M 2025 $1,087 $1,447 $1,647 $1,951 $2,423 $1,879 $2,254 2020 2021 2022 2023 2024 9M 2024 9M 2025 Hamilton Group – Strategic Growth and Sustainable Underwriting Profitability Hamilton Group - Gross Premiums Written ($’m) Hamilton Group - Combined Ratio (2) Loss Ratio Expense Ratio (3) 1) Compound annual growth rate. 2) Numbers may not add due to rounding. 3) Combined ratio excluding the Ukraine Conflict was 96%. Double digit top line growth with bottom line improvement

10 International Segment: Market Leading Writer of Specialty (Re)Insurance Business Specialty insurance products written in Lloyd’s, Hamilton Insurance DAC, HMGA Americas & Hamilton Select 15% 42% 43% Property Casualty Specialty 2024 GPW Business Mix 88% 12% Insurance Reinsurance $1.3B Hamilton Select $117m / 9% Hamilton Global Specialty ▪ Lloyd’s Syndicate 4000 and Hamilton Insurance DAC (Ireland) ▪ Ability to offer both Lloyd’s and company paper increases access to business ▪ Longstanding client & broker relationships fuel growth in core E&S markets ▪ $1.2 billion of gross premiums written in 2024 ▪ Limited legacy exposures prior to 2019 Hamilton Select ▪ U.S. domiciled surplus lines carrier specializing in small to midsize, hard-to-place lines of business Highlights

11 65% 63% 54% 52% 56% 56% 54% 46% 44% 43% 43% 39% 39% 41% 111% 108% 97% 95% 96% 95% 95% 2020 2021 2022 2023 2024 9M 2024 9M 2025 (3) Results reflect the diversified, lower volatility portfolio we have built over time International Segment: Measured Growth and Profitability Improvement $662 $892 $933 $1,106 $1,308 $958 $1,095 2020 2021 2022 2023 2024 9M 2024 9M 2025 International Segment - Gross Premiums Written ($’m) International Segment - Combined Ratio (2) Loss Ratio Expense Ratio 1) Compound annual growth rate. 2) Numbers may not add due to rounding. 3) Combined ratio excluding the Ukraine Conflict was 93%.

12 Bermuda Segment: Well Diversified Writer of Property, Casualty and Specialty Classes Underwriting-focused operation with strong foundation to capture growth opportunities 38% 47% 15% Property Casualty Specialty 12% 88% Insurance Reinsurance 2024 GPW Business Mix $1.1B Hamilton Re ▪ Established, scaled and scalable platform with broad, diversified client base ▪ Demonstrated underwriting profitability through portfolio optimization and thoughtful cycle management ▪ Strategic growth enhanced by diversified product offering: property, casualty and specialty ▪ Reinsurance business written both by Bermuda and US underwriting teams ▪ Clear, consistent appetite and responsive service rewarded by clients and brokers ▪ Data-driven approach supports underwriting and operational efficiencies Highlights

13 Current portfolio mix has resulted in meaningful growth and improved underwriting results Bermuda Segment: Strategic Growth Following Portfolio Optimization 81% 75% 81% 57% 60% 59% 69% 31% 29% 29% 28% 27% 26% 27% 111% 104% 110% 85% 87% 84% 96% 2020 2021 2022 2023 2024 9M 2024 9M 2025 $425 $554 $713 $846 $1,114 $921 $1,159 2020 2021 2022 2023 2024 9M 2024 9M 2025 Bermuda Segment - Gross Premiums Written ($’m) Bermuda Segment - Combined Ratio (2) Loss Ratio Expense Ratio 1) Compound annual growth rate. 2) Numbers may not add due to rounding. 3) Combined ratio excluding the Ukraine Conflict was 101%. (3)

15 Two Sigma Hamilton FundFixed Income PortfolioA B Preservation of Capital 1 Liquidity 2 Diversification 3 Attractive Returns 4 Risk Management & Governance 5 ✓ Aa3 average credit quality 100% investment grade ✓ Highly liquid ✓ Market sector diversification ✓ 4.3% book yield 3Q 2025 ✓ Investment guidelines from Investment Committee ✓ Low correlation to equity markets; long- term positive returns ✓ Redeemable within 5 days ✓ 7 unique investment vehicles ✓ 13.0% annualized return since inception (2014) ✓ Hold lesser of $1.8B or 60% of Hamilton net tangible assets in TSHF; arms- length IMA* with Two Sigma Investment Strategy Review – $5.7 Billion Investment Portfolio as of September 30, 2025 Fixed Income, Short-Term and Cash 62.6% / $3.6B Two Sigma Hamilton Fund 37.4% / $2.1B *Investment management agreement (“IMA”).

16 Fixed Income Investment Portfolio as of September 30, 2025 49% 28% 12% 11% Corporate US Treasury US Agency Other $3.0B Corporate A3 US Treas. Aa1 US Agency Aa1 Other Aa1 Fixed income portfolio is managed by two external managers Fixed income investments of $3.0 billion – Average rating of Aa3, and duration of 3.3 years

17 Overview of Two Sigma and TSHF Diversified fund focused on liquid strategies in global equities, fixed income, futures, and FX markets ▪ Two Sigma Investment Management aims to deliver low-correlated absolute returns primarily through the systematic and non- systematic application of fundamental, technical, alpha capture and event models ▪ Manages over $70B in assets ▪ Deploys and seeks to continuously improve intelligent investment management systems first created in 2001 ▪ Proven, industry leading approach to data science and analytics ▪ Over 1,700 employees of which include an experienced and diverse team of employees in R&D ▪ Seeks to systematically manage risk with human oversight at multiple levels through the investment process ▪ TSHF is a diversified fund focused on liquid strategies in global equities, fixed income, futures and FX markets Two Sigma Hamilton Fund $2.1B TSHF as of September 30, 2025 13.0% Average annualized returns 2014-3Q 2025 Dedicated- fund of one Allocation 70% equities 30% macro Highly liquid Investments TSHF Annual Returns Since 2018 Two Sigma Hamilton Fund, LLC (“TSHF”) 1.41 Sharpe Ratio since inception 19.9% 6.1% -4.6% 17.7% 4.6% 7.6% 16.3% 2018 2019 2020 2021 2022 2023 2024 1) TSHF Annual Returns correspond to Hamilton fiscal year which was Dec 1- Nov 30 until FY 2022.

19 5 A scaled, diversified, global specialty insurance and reinsurance operation Highly entrepreneurial & experienced leadership team fostering a distinctive and attractive culture Disciplined underwriting approach focused on sustainable profitability Strong balance sheet with significant financial flexibility Strong financial strength ratings including an AM Best “A” rating for Hamilton Re and HIDAC Differentiated asset management capabilities due to unique partnership with Two Sigma Demonstrated ability to grow profitably, navigating across market cycles Poised to Deliver Significant Shareholder Value Hamilton Insurance Group – Who We Are Today

20 Non-GAAP Measures We present our results of operations in a way that we believe will be the most meaningful and useful to investors, analysts, rating agencies and others who use our financial information to evaluate our performance. Some of the measurements that management uses to assess our operating results are considered non-GAAP financial measures under Regulation G and Item 10(e) of Regulation S-K, each promulgated by the SEC. We believe that these non- GAAP financial measures, which may be defined and calculated differently by other companies, help explain and enhance the understanding of our results of operations. However, these measures should not be viewed as a substitute for those determined in accordance with U.S. GAAP. Where appropriate, reconciliations of our non-GAAP measures to the most directly comparable GAAP financial measures are included below. Underwriting Income (Loss) We calculate underwriting income (loss) on a pre-tax basis as net premiums earned less losses and loss adjustment expenses, acquisition costs and other underwriting expenses (net of third party fee income). We believe that this measure of our performance focuses on the core fundamental performance of the Company’s reportable segments in any given period and is not distorted by investment market conditions, corporate expense allocations or income tax effects. The table below reconciles underwriting income (loss) to net income (loss), the most directly comparable GAAP financial measure:

Hamilton Insurance Group, Ltd. Wellesley House North, 1st Floor 90 Pitts Bay Road, Pembroke HM08, Bermuda +1 (441) 405 5200 hamiltongroup.com Contact us at: Investor.Relations@hamiltongroup.com