Hamilton Insurance Group, Ltd. Supplementary Financial Information June 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 June 30, Six Months Ended June 30, Year Ended ($ in thousands) 2025 2024 2025 2024 2024 Net income (loss) attributable to common shareholders ........................................................ $ 187,415 $ 131,085 $ 268,288 $ 288,259 $ 400,429 Operating income (loss) attributable to common shareholders ............................................ $ 161,803 $ 135,886 $ 211,191 $ 311,121 $ 414,591 Underwriting income (loss) Gross premiums written ............................................................................................................... $ 712,026 $ 603,304 $ 1,555,332 $ 1,325,245 $ 2,422,582 Net premiums written ................................................................................................................... 556,314 475,068 1,160,189 989,948 1,921,169 Net premiums earned .................................................................................................................. 511,163 418,764 1,010,091 804,067 1,734,729 Underwriting income (loss) .......................................................................................................... $ 67,459 $ 65,299 $ 9,199 $ 97,825 $ 149,364 Key Ratios: Attritional loss ratio - current year .............................................................................................. 53.0 % 51.6 % 52.5 % 54.3 % 53.1 % Attritional loss ratio - prior year development ........................................................................... (0.5) % (0.4) % (1.7) % 1.3 % 0.0 % Catastrophe loss ratio - current year ......................................................................................... 1.9 % 0.0 % 16.8 % 0.0 % 6.3 % Catastrophe loss ratio - prior year development ...................................................................... (1.6) % 0.0 % (1.7) % 0.0 % (1.2) % Loss and loss adjustment expense ratio ................................................................................... 52.8 % 51.2 % 65.9 % 55.6 % 58.2 % Acquisition cost ratio .................................................................................................................... 24.0 % 23.0 % 23.7 % 22.5 % 22.4 % Other underwriting expense ratio ............................................................................................... 10.0 % 10.2 % 9.5 % 9.8 % 10.7 % Combined ratio .............................................................................................................................. 86.8 % 84.4 % 99.1 % 87.9 % 91.3 % Investments Total assets .................................................................................................................................... $ 8,913,050 $ 7,623,103 $ 8,913,050 $ 7,623,103 $ 7,796,033 Total cash and invested assets(1) ............................................................................................... 5,321,894 4,351,728 5,321,894 4,351,728 4,773,236 Total investment return(2) ............................................................................................................. 148,730 95,674 316,057 243,505 361,945 Two Sigma Hamilton Fund Total net realized and unrealized gains (losses) on investments and net investment income (loss) - TSHF ................................................................................................................... 167,457 145,183 371,418 408,002 487,186 Net income (loss) attributable to non-controlling interest - TSHF ......................................... 80,371 69,297 180,765 189,455 212,729 $ 87,086 $ 75,886 $ 190,653 $ 218,547 $ 274,457 Two Sigma Hamilton Fund return, net of investment management fees and performance incentive allocations .............................................................................................. 4.4 % 4.3 % 10.1 % 12.9 % 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 .................................................................................................................... $ 61,644 $ 19,788 $ 125,404 $ 24,958 $ 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 June 30, Six Months Ended June 30, Year Ended ($ in thousands, except per share amounts) 2025 2024 2025 2024 2024 Income (loss) per share attributable to common shareholders - basic ............................................ $ 1.85 $ 1.24 $ 2.64 $ 2.66 $ 3.81 Income (loss) per share attributable to common shareholders - diluted .......................................... $ 1.79 $ 1.20 $ 2.56 $ 2.57 $ 3.67 Operating income (loss) attributable to common shareholders per common share - diluted ....... $ 1.55 $ 1.24 $ 2.01 $ 2.78 $ 3.80 Weighted average common shares outstanding - basic .................................................................... 101,421,322 105,909,397 101,679,121 108,416,011 105,133,370 Weighted average common shares outstanding - diluted .................................................................. 104,568,161 109,603,699 104,915,497 112,072,457 109,101,714 Return on average common shareholders' equity - annualized ........................................................ 30.2 % 23.6 % 22.0 % 26.9 % 18.3 % Operating return on average common shareholders' equity - annualized ....................................... 26.1 % 24.4 % 17.3 % 29.0 % 18.9 % June 30, 2025 December 31, 2024 Closing common shareholders' equity, less intangible assets .......................................................... $ 2,468,530 $ 2,235,588 Closing common shareholders' equity .................................................................................................. $ 2,558,591 $ 2,328,709 Closing common shares outstanding .................................................................................................... 100,140,859 101,466,997 Tangible book value per common share ............................................................................................... $ 24.65 $ 22.03 Book value per common share ............................................................................................................... $ 25.55 $ 22.95 Year to date change in tangible book value per common share ....................................................... 11.9 % 24.1 % Year to date change in book value per common share ...................................................................... 11.3 % 23.5 % Financial Highlights Key Operating and Financial Metrics

6 Three Months Ended June 30, Six Months Ended June 30, Year Ended ($ in thousands, except per share amounts) 2025 2024 2025 2024 2024 Revenues Gross premiums written ....................................................................................................................... $ 712,026 $ 603,304 $ 1,555,332 $ 1,325,245 $ 2,422,582 Reinsurance premiums ceded ............................................................................................................ (155,712) (128,236) (395,143) (335,297) (501,413) Net premiums written ........................................................................................................................... 556,314 475,068 1,160,189 989,948 1,921,169 Net change in unearned premiums .................................................................................................... (45,151) (56,304) (150,098) (185,881) (186,440) Net premiums earned .......................................................................................................................... 511,163 418,764 1,010,091 804,067 1,734,729 Net realized and unrealized gains (losses) on investments .......................................................... 208,034 151,251 456,828 406,622 511,407 Net investment income (loss) ............................................................................................................. 21,067 13,720 39,994 26,338 63,267 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ....................................................................................................................................................... 229,101 164,971 496,822 432,960 574,674 Third party fee income ......................................................................................................................... 5,014 5,989 9,676 13,470 23,752 Net foreign exchange gains (losses) ................................................................................................. (4,513) (1,782) (7,039) (3,911) (3,231) Total revenues ..................................................................................................................................... 740,765 587,942 1,509,550 1,246,586 2,329,924 Expenses Losses and loss adjustment expenses ............................................................................................. 269,928 214,494 665,163 446,846 1,010,173 Acquisition costs ................................................................................................................................... 122,815 96,305 239,696 180,858 388,931 Other underwriting expenses .............................................................................................................. 55,975 48,655 105,709 92,008 210,013 Corporate expenses ............................................................................................................................. 12,853 16,262 25,821 27,764 61,111 Amortization of intangible assets ....................................................................................................... 4,004 3,317 7,895 6,569 15,520 Interest expense ................................................................................................................................... 4,729 6,031 10,331 11,738 22,616 Total expenses .................................................................................................................................... 470,304 385,064 1,054,615 765,783 1,708,364 Income (loss) before income tax ........................................................................................................ 270,461 202,878 454,935 480,803 621,560 Income tax expense (benefit) ............................................................................................................. 2,675 2,496 5,882 3,089 8,402 Net income (loss) ................................................................................................................................ 267,786 200,382 449,053 477,714 613,158 Net income (loss) attributable to non-controlling interest ............................................................... 80,371 69,297 180,765 189,455 212,729 Net income (loss) and other comprehensive income (loss) attributable to common shareholders ........................................................................................................................................ $ 187,415 $ 131,085 $ 268,288 $ 288,259 $ 400,429 Per share data Income (loss) per share attributable to common shareholders - basic ........................................ $ 1.85 $ 1.24 $ 2.64 $ 2.66 $ 3.81 Income (loss) per share attributable to common shareholders - diluted ...................................... $ 1.79 $ 1.20 $ 2.56 $ 2.57 $ 3.67 Return on average common shareholders' equity - annualized .................................................... 30.2 % 23.6 % 22.0 % 26.9 % 18.3 % Summary Consolidated Results Statements of Operations

7 June 30, March 31, December 31, September 30, June 30, ($ in thousands, except share information) 2025 2025 2024 2024 2024 Assets Fixed maturity investments, at fair value (amortized cost June 30, 2025: $2,680,466) ................................................. $ 2,698,470 $ 2,425,986 $ 2,377,862 $ 2,320,184 $ 2,068,930 Short-term investments, at fair value (amortized cost June 30, 2025: $306,442) .......................................................... 307,129 406,207 497,110 507,947 463,542 Investments in Two Sigma Funds, at fair value (cost June 30, 2025: $1,240,592) ........................................................ 1,453,781 1,341,079 939,381 932,787 923,682 Total investments ....................................................................................................................................................................... 4,459,380 4,173,272 3,814,353 3,760,918 3,456,154 Cash and cash equivalents ...................................................................................................................................................... 985,649 838,514 996,493 957,372 1,016,573 Restricted cash and cash equivalents ................................................................................................................................... 85,648 74,548 104,359 93,883 98,279 Premiums receivable ................................................................................................................................................................ 1,048,580 989,656 771,707 885,744 933,211 Paid losses recoverable ........................................................................................................................................................... 131,833 91,701 134,406 146,008 147,690 Deferred acquisition costs ........................................................................................................................................................ 253,402 242,346 208,985 205,953 203,279 Unpaid losses and loss adjustment expenses recoverable ................................................................................................ 1,236,660 1,235,045 1,171,040 1,190,465 1,160,309 Receivables for investments sold ........................................................................................................................................... 38,271 46,358 74,006 39,079 12,307 Prepaid reinsurance .................................................................................................................................................................. 360,890 329,213 218,921 260,174 299,574 Intangible assets ........................................................................................................................................................................ 90,061 91,184 93,121 94,441 94,410 Other assets ............................................................................................................................................................................... 222,676 230,994 208,642 192,510 201,317 Total assets .............................................................................................................................................................................. $ 8,913,050 $ 8,342,831 $ 7,796,033 $ 7,826,547 $ 7,623,103 Liabilities, non-controlling interest, and shareholders' equity Liabilities Reserve for losses and loss adjustment expenses .............................................................................................................. $ 3,984,281 $ 3,815,307 $ 3,532,491 $ 3,434,800 $ 3,242,893 Unearned premiums ................................................................................................................................................................. 1,414,344 1,337,516 1,122,277 1,192,071 1,202,371 Reinsurance balances payable ............................................................................................................................................... 417,251 346,240 261,275 334,511 399,633 Payables for investments purchased ..................................................................................................................................... 127,529 46,925 115,427 172,905 111,280 Term loan, net of issuance costs ............................................................................................................................................ 149,691 149,974 149,945 149,916 149,887 Accounts payable and accrued expenses ............................................................................................................................. 141,838 137,667 185,361 168,658 158,187 Payables to related parties ...................................................................................................................................................... 50,233 70,709 100,420 — 43,030 Total liabilities .......................................................................................................................................................................... 6,285,167 5,904,338 5,467,196 5,452,861 5,307,281 Non-controlling interest - TS Hamilton Fund ................................................................................................................... 69,292 39,154 128 60,060 77,275 Shareholders' equity Common shares: Class A, authorized (June 30, 2025: 26,944,807), par value $0.01; issued and outstanding (June 30, 2025: 17,820,078) ................................................................................................................................................................................ 178 178 178 178 195 Class B, authorized (June 30, 2025: 83,577,932), par value $0.01; issued and outstanding (June 30, 2025: 66,317,132) ................................................................................................................................................................................ 663 660 643 637 574 Class C, authorized (June 30, 2025: 16,003,649), par value $0.01; issued and outstanding (June 30, 2025: 16,003,649) ................................................................................................................................................................................ 160 179 194 199 250 Additional paid-in-capital .......................................................................................................................................................... 1,148,571 1,160,569 1,163,609 1,172,331 1,171,585 Accumulated other comprehensive loss ................................................................................................................................ (4,441) (4,441) (4,441) (4,441) (4,441) Retained earnings ..................................................................................................................................................................... 1,413,460 1,242,194 1,168,526 1,144,722 1,070,384 Total shareholders' equity .................................................................................................................................................... 2,558,591 2,399,339 2,328,709 2,313,626 2,238,547 Total liabilities, non-controlling interest, and shareholders' equity ......................................................................... $ 8,913,050 $ 8,342,831 $ 7,796,033 $ 7,826,547 $ 7,623,103 Summary Consolidated Results Consolidated Balance Sheets

8 June 30, 2025 ($ in thousands) Consolidated GAAP Balance Sheet Two Sigma Hamilton Fund Balances Unconsolidated Balance Sheet(1) Assets Fixed maturity investments, at fair value .................................................................................................................................................................................... $ 2,698,470 $ - $ 2,698,470 Short-term investments, at fair value ......................................................................................................................................................................................... 307,129 (285,385) 21,744 Investments in Two Sigma Funds, at fair value ........................................................................................................................................................................ 1,453,781 614,167 2,067,948 Total investments ............................................................................................................................................................................................................................ 4,459,380 328,782 4,788,162 Cash and cash equivalents .......................................................................................................................................................................................................... 985,649 (521,551) 464,098 Restricted cash and cash equivalents ........................................................................................................................................................................................ 85,648 - 85,648 Premiums receivable ..................................................................................................................................................................................................................... 1,048,580 - 1,048,580 Paid losses recoverable ................................................................................................................................................................................................................ 131,833 - 131,833 Deferred acquisition costs ............................................................................................................................................................................................................ 253,402 - 253,402 Unpaid losses and loss adjustment expenses recoverable .................................................................................................................................................... 1,236,660 - 1,236,660 Receivables for investments sold ................................................................................................................................................................................................ 38,271 (30,758) 7,513 Prepaid reinsurance ....................................................................................................................................................................................................................... 360,890 - 360,890 Intangible assets ............................................................................................................................................................................................................................ 90,061 - 90,061 Other assets .................................................................................................................................................................................................................................... 222,676 (1,576) 221,100 Total assets ................................................................................................................................................................................................................................... $ 8,913,050 $ (225,103) $ 8,687,947 Liabilities, non-controlling interest, and shareholders' equity Liabilities Reserve for losses and loss adjustment expenses .................................................................................................................................................................. $ 3,984,281 $ - $ 3,984,281 Unearned premiums ...................................................................................................................................................................................................................... 1,414,344 - 1,414,344 Reinsurance balances payable .................................................................................................................................................................................................... 417,251 - 417,251 Payables for investments purchased .......................................................................................................................................................................................... 127,529 (105,396) 22,133 Term loan, net of issuance costs ................................................................................................................................................................................................. 149,691 - 149,691 Accounts payable and accrued expenses .................................................................................................................................................................................. 141,838 (182) 141,656 Payables to related parties ........................................................................................................................................................................................................... 50,233 (50,233) - Total liabilities ............................................................................................................................................................................................................................... 6,285,167 (155,811) 6,129,356 Non-controlling interest - TS Hamilton Fund ....................................................................................................................................................................... 69,292 (69,292) - Shareholders' equity Common shares: Class A, par value $0.01 ............................................................................................................................................................................................................... 178 - 178 Class B, par value $0.01 ............................................................................................................................................................................................................... 663 - 663 Class C, par value $0.01 ............................................................................................................................................................................................................... 160 - 160 Additional paid-in-capital ............................................................................................................................................................................................................... 1,148,571 - 1,148,571 Accumulated other comprehensive loss ..................................................................................................................................................................................... (4,441) - (4,441) Retained earnings .......................................................................................................................................................................................................................... 1,413,460 - 1,413,460 Total shareholders' equity ......................................................................................................................................................................................................... 2,558,591 - 2,558,591 Total liabilities, non-controlling interest, and shareholders' equity .............................................................................................................................. $ 8,913,050 $ (225,103) $ 8,687,947 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 June 30, Six Months Ended June 30, Year Ended ($ in thousands) 2025 2024 2025 2024 2024 Net realized gains (losses) on investments ............................................................ $ 196,129 $ 139,489 $ 314,787 $ 288,934 $ 468,068 Fixed maturities and short-term investments ............................................................ 1,343 (1,695) 867 (4,636) (2,307) TS Hamilton Fund ......................................................................................................... 194,786 140,900 313,920 293,286 470,091 Other................................................................................................................................ — 284 — 284 284 Change in net unrealized gains (losses) on investments ................................... 11,905 11,762 142,041 117,688 43,339 Fixed maturities and short-term investments ............................................................ 28,782 (1,608) 63,269 (14,599) (8,908) TS Hamilton Fund ......................................................................................................... (16,877) 13,370 78,772 132,287 52,247 Net realized and unrealized gains (losses) on investments .............................. 208,034 151,251 456,828 406,622 511,407 Net investment income (loss): Fixed maturities ................................................................................................................ 27,317 19,009 52,604 35,960 81,872 Short-term investments ................................................................................................... 230 41 298 40 67 TS Hamilton Fund ............................................................................................................ 2,858 2,917 4,594 5,932 12,373 Cash and cash equivalents ............................................................................................ 3,987 4,095 8,590 8,210 17,006 Other .................................................................................................................................. 726 415 1,186 1,167 2,293 Interest and other .......................................................................................................... 35,118 26,477 67,272 51,309 113,611 Management fees ........................................................................................................... (13,719) (12,482) (26,685) (24,433) (49,102) Fixed maturities and short-term investments ............................................................ (636) (620) (1,201) (1,212) (2,192) TS Hamilton Fund ......................................................................................................... (13,083) (11,862) (25,484) (23,221) (46,910) Other expenses .............................................................................................................. (332) (275) (593) (538) (1,242) Fixed maturities and short-term investments ............................................................ (105) (133) (209) (256) (627) TS Hamilton Fund ......................................................................................................... (227) (142) (384) (282) (615) Net investment income (loss) ..................................................................................... 21,067 13,720 39,994 26,338 63,267 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ............................................................................................ 229,101 164,971 496,822 432,960 574,674 Net income (loss) attributable to non-controlling interest .......................................... 80,371 69,297 180,765 189,455 212,729 Total net realized and unrealized gains (losses) on investments and net investment income (loss), net of non-controlling interest ................................. $ 148,730 $ 95,674 $ 316,057 $ 243,505 $ 361,945 Fixed income, short-term investments and cash and cash equivalents return ...... $ 61,644 $ 19,788 $ 125,404 $ 24,958 $ 87,488 TS Hamilton Fund return(1) ............................................................................................. $ 87,086 $ 75,886 $ 190,653 $ 218,547 274,457 Summary Consolidated Results Net Investment Return (1) Net of non-controlling interest performance incentive allocation

10 June 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 ...................................................................... $ 729,156 24% Aa1 $ 711,103 25% Aaa U.S. states, territories and municipalities ............................................... 12,813 0% Aa2 13,231 0% Aa2 Non-U.S. sovereign governments and supranationals ......................... 94,513 3% Aa1 67,527 2% Aa1 Corporate ..................................................................................................... 1,327,713 45% A2 1,143,060 41% A3 Residential mortgage-backed securities - Agency ................................ 319,603 11% Aa1 272,611 9% Aaa Residential mortgage-backed securities - Non-agency ....................... 29,458 1% Aaa 16,754 1% Aaa Commercial mortgage-backed securities - Non-agency ...................... 53,270 2% Aa1 39,686 1% Aaa Other asset-backed securities .................................................................. 131,944 4% Aaa 113,890 4% Aaa Total fixed maturities .................................................................................. 2,698,470 90% Aa3 2,377,862 83% Aa3 Short-term investments ................................................................................ 307,129 10% Aa1 497,110 17% Aaa Total fixed maturities and short-term investments ................................. $ 3,005,599 100% 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) June 30, 2025 December 31, 2024 Average credit quality ................................................................................... Aa3 Aa3 Average yield to maturity ............................................................................. 4.3% 4.7% Book yield ....................................................................................................... 4.3% 4.1% Expected average duration (in years) ....................................................... 3.4 3.4 (1) Includes $285.4 million and $496.0 million of short-term investments, at June 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 June 30, 2025 Three Months Ended June 30, 2024 ($ in thousands) International Bermuda Total International Bermuda Total Gross premiums written ........................................................................ $ 344,799 $ 367,227 $ 712,026 $ 311,616 $ 291,688 $ 603,304 Net premiums written ............................................................................. 258,089 298,225 556,314 234,305 240,763 475,068 Net premiums earned ............................................................................ 253,209 257,954 511,163 215,643 203,121 418,764 Third party fee income ........................................................................... 3,832 1,182 5,014 3,798 2,191 5,989 Losses and loss adjustment expenses ............................................... 124,733 145,195 269,928 112,884 101,610 214,494 Acquisition costs ..................................................................................... 65,683 57,132 122,815 53,157 43,148 96,305 Other underwriting expenses ................................................................ 39,507 16,468 55,975 33,972 14,683 48,655 Underwriting income (loss) ................................................................... $ 27,118 $ 40,341 $ 67,459 $ 19,428 $ 45,871 $ 65,299 Key Ratios: Attritional loss ratio - current year ........................................................ 51.9 % 54.2 % 53.0 % 52.5 % 50.5 % 51.6 % Attritional loss ratio - prior year development .................................... (3.0) % 2.0 % (0.5) % (0.2) % (0.5) % (0.4) % Catastrophe loss ratio - current year ................................................... 0.6 % 3.2 % 1.9 % 0.0 % 0.0 % 0.0 % Catastrophe loss ratio - prior year development ............................... (0.2) % (3.1) % (1.6) % 0.0 % 0.0 % 0.0 % Loss and loss adjustment expense ratio ............................................ 49.3 % 56.3 % 52.8 % 52.3 % 50.0 % 51.2 % Acquisition cost ratio .............................................................................. 25.9 % 22.1 % 24.0 % 24.7 % 21.2 % 23.0 % Other underwriting expense ratio ......................................................... 14.1 % 5.9 % 10.0 % 14.0 % 6.2 % 10.2 % Combined ratio ........................................................................................ 89.3 % 84.3 % 86.8 % 91.0 % 77.4 % 84.4 % Segment Results Consolidated Underwriting Results

12 Six Months Ended June 30, 2025 Six Months Ended June 30, 2024 ($ in thousands) International Bermuda Total International Bermuda Total Gross premiums written ......................................................................... $ 714,757 $ 840,575 $ 1,555,332 $ 632,457 $ 692,788 $ 1,325,245 Net premiums written .............................................................................. 487,063 673,126 1,160,189 419,338 570,610 989,948 Net premiums earned ............................................................................. 493,775 516,316 1,010,091 412,456 391,611 804,067 Third party fee income ............................................................................ 8,164 1,512 9,676 7,387 6,083 13,470 Losses and loss adjustment expenses ................................................ 270,405 394,758 665,163 229,046 217,800 446,846 Acquisition costs ...................................................................................... 128,473 111,223 239,696 100,876 79,982 180,858 Other underwriting expenses ................................................................ 75,130 30,579 105,709 65,174 26,834 92,008 Underwriting income (loss) .................................................................... $ 27,931 $ (18,732) $ 9,199 $ 24,747 $ 73,078 $ 97,825 Key Ratios: Attritional loss ratio - current year ......................................................... 52.0 % 53.0 % 52.5 % 54.2 % 54.3 % 54.3 % Attritional loss ratio - prior year development ..................................... (3.3) % (0.1) % (1.7) % 1.3 % 1.3 % 1.3 % Catastrophe loss ratio - current year .................................................... 6.2 % 26.9 % 16.8 % 0.0 % 0.0 % 0.0 % Catastrophe loss ratio - prior year development ................................ (0.1) % (3.3) % (1.7) % 0.0 % 0.0 % 0.0 % Loss and loss adjustment expense ratio ............................................. 54.8 % 76.5 % 65.9 % 55.5 % 55.6 % 55.6 % Acquisition cost ratio ............................................................................... 26.0 % 21.5 % 23.7 % 24.5 % 20.4 % 22.5 % Other underwriting expense ratio ......................................................... 13.6 % 5.6 % 9.5 % 14.0 % 5.3 % 9.8 % Combined ratio ........................................................................................ 94.4 % 103.6 % 99.1 % 94.0 % 81.3 % 87.9 % Segment Results Consolidated Underwriting Results

13 Three Months Ended Six Months Ended Year Ended June 30, March 31, December 31, September 30, June 30, June 30, June 30, December 31, ($ in thousands) 2025 2025 2024 2024 2024 2025 2024 2024 Gross premiums written ........................................... $ 712,026 $ 843,306 $ 543,937 $ 553,401 $ 603,304 $ 1,555,332 $ 1,325,245 $ 2,422,582 Net premiums written ................................................ 556,314 603,875 453,326 477,896 475,068 1,160,189 989,948 1,921,169 Net premiums earned ............................................... 511,163 498,928 481,867 448,795 418,764 1,010,091 804,067 1,734,729 Third party fee income .............................................. 5,014 4,662 5,818 4,464 5,989 9,676 13,470 23,752 Losses and loss adjustment expenses .................. 269,928 395,234 289,695 273,632 214,494 665,163 446,846 1,010,173 Acquisition costs ........................................................ 122,815 116,881 105,872 102,201 96,305 239,696 180,858 388,931 Other underwriting expenses .................................. 55,975 49,734 69,674 48,332 48,655 105,709 92,008 210,013 Underwriting income (loss) ...................................... $ 67,459 $ (58,259) $ 22,444 $ 29,094 $ 65,299 $ 9,199 $ 97,825 $ 149,364 Key Ratios: Attritional loss ratio - current year ........................... 53.0 % 51.9 % 51.2 % 53.2 % 51.6 % 52.5 % 54.3 % 53.1 % Attritional loss ratio - prior year development ....... (0.5) % (2.9) % (1.3) % (0.7) % (0.4) % (1.7) % 1.3 % 0.0 % Catastrophe loss ratio - current year ...................... 1.9 % 32.0 % 11.9 % 11.5 % 0.0 % 16.8 % 0.0 % 6.3 % Catastrophe loss ratio - prior year development .. (1.6) % (1.8) % (1.7) % (3.0) % 0.0 % (1.7) % 0.0 % (1.2) % Loss and loss adjustment expense ratio ............... 52.8 % 79.2 % 60.1 % 61.0 % 51.2 % 65.9 % 55.6 % 58.2 % Acquisition cost ratio ................................................. 24.0 % 23.4 % 22.0 % 22.8 % 23.0 % 23.7 % 22.5 % 22.4 % Other underwriting expense ratio ............................ 10.0 % 9.0 % 13.3 % 9.8 % 10.2 % 9.5 % 9.8 % 10.7 % Combined ratio .......................................................... 86.8 % 111.6 % 95.4 % 93.6 % 84.4 % 99.1 % 87.9 % 91.3 % Gross premiums written Property ...................................................................... $ 207,488 $ 277,603 $ 77,378 $ 120,001 $ 188,561 $ 485,091 $ 416,737 $ 614,116 Casualty ...................................................................... 322,446 315,097 298,607 272,998 255,627 637,542 507,520 1,079,124 Specialty ..................................................................... 182,092 250,606 167,952 160,402 159,116 432,699 400,988 729,342 Total .......................................................................... $ 712,026 $ 843,306 $ 543,937 $ 553,401 $ 603,304 $ 1,555,332 $ 1,325,245 $ 2,422,582 Net premiums earned Property ...................................................................... $ 124,019 $ 141,173 $ 122,734 $ 121,766 $ 106,553 $ 265,192 $ 213,262 $ 457,762 Casualty ...................................................................... 232,047 217,672 205,234 193,948 175,237 449,719 334,347 733,529 Specialty ..................................................................... 155,097 140,083 153,899 133,081 136,974 295,180 256,458 543,438 Total .......................................................................... $ 511,163 $ 498,928 $ 481,867 $ 448,795 $ 418,764 $ 1,010,091 $ 804,067 $ 1,734,729 Segment Results 5Q Consolidated Underwriting Results - Group

14 Three Months Ended Six Months Ended Year Ended June 30, March 31, December 31, September 30, June 30, June 30, June 30, December 31, ($ in thousands) 2025 2025 2024 2024 2024 2025 2024 2024 Gross premiums written ........................................... $ 344,799 $ 369,959 $ 350,479 $ 325,525 $ 311,616 $ 714,757 $ 632,457 $ 1,308,460 Net premiums written ................................................ 258,089 228,975 282,161 268,106 234,305 487,063 419,338 969,605 Net premiums earned ............................................... 253,209 240,567 249,234 225,244 215,643 493,775 412,456 886,934 Third party fee income .............................................. 3,832 4,332 4,760 4,170 3,798 8,164 7,387 16,317 Losses and loss adjustment expenses .................. 124,733 145,671 138,842 130,135 112,884 270,405 229,046 498,023 Acquisition costs ........................................................ 65,683 62,790 56,382 59,713 53,157 128,473 100,876 216,971 Other underwriting expenses .................................. 39,507 35,623 49,507 34,143 33,972 75,130 65,174 148,824 Underwriting income (loss) ...................................... $ 27,118 $ 815 $ 9,263 $ 5,423 $ 19,428 $ 27,931 $ 24,747 $ 39,433 Key Ratios: Attritional loss ratio - current year ........................... 51.9 % 52.1 % 50.8 % 55.3 % 52.5 % 52.0 % 54.2 % 53.5 % Attritional loss ratio - prior year development ....... (3.0) % (3.6) % (2.1) % (1.5) % (0.2) % (3.3) % 1.3 % (0.4) % Catastrophe loss ratio - current year ...................... 0.6 % 12.1 % 7.8 % 6.4 % 0.0 % 6.2 % 0.0 % 3.9 % Catastrophe loss ratio - prior year development .. (0.2) % 0.0 % (0.8) % (2.4) % 0.0 % (0.1) % 0.0 % (0.8) % Loss and loss adjustment expense ratio ............... 49.3 % 60.6 % 55.7 % 57.8 % 52.3 % 54.8 % 55.5 % 56.2 % Acquisition cost ratio ................................................. 25.9 % 26.1 % 22.6 % 26.5 % 24.7 % 26.0 % 24.5 % 24.5 % Other underwriting expense ratio ............................ 14.1 % 13.0 % 18.0 % 13.3 % 14.0 % 13.6 % 14.0 % 14.9 % Combined ratio .......................................................... 89.3 % 99.7 % 96.3 % 97.6 % 91.0 % 94.4 % 94.0 % 95.6 % Gross premiums written Property ...................................................................... $ 63,871 $ 54,526 $ 47,684 $ 51,441 $ 53,540 $ 118,397 $ 91,244 $ 190,369 Casualty ...................................................................... 140,441 135,563 157,013 144,107 132,129 276,003 253,294 554,413 Specialty ..................................................................... 140,487 179,870 145,782 129,977 125,947 320,357 287,919 563,678 Total .......................................................................... $ 344,799 $ 369,959 $ 350,479 $ 325,525 $ 311,616 $ 714,757 $ 632,457 $ 1,308,460 Net premiums earned Property ...................................................................... $ 43,706 $ 45,705 $ 44,621 $ 37,033 $ 32,689 $ 89,410 $ 67,664 $ 149,318 Casualty ...................................................................... 89,233 90,568 84,776 86,062 75,770 179,801 148,698 319,536 Specialty ..................................................................... 120,270 104,294 119,837 102,149 107,184 224,564 196,094 418,080 Total .......................................................................... $ 253,209 $ 240,567 $ 249,234 $ 225,244 $ 215,643 $ 493,775 $ 412,456 $ 886,934 Segment Results 5Q Underwriting Results - International

15 Three Months Ended Six Months Ended Year Ended June 30, March 31, December 31, September 30, June 30, June 30, June 30, December 31, ($ in thousands) 2025 2025 2024 2024 2024 2025 2024 2024 Gross premiums written ........................................... $ 367,227 $ 473,347 $ 193,458 $ 227,876 $ 291,688 $ 840,575 $ 692,788 $ 1,114,122 Net premiums written ................................................ 298,225 374,900 171,165 209,790 240,763 673,126 570,610 951,564 Net premiums earned ............................................... 257,954 258,361 232,633 223,551 203,121 516,316 391,611 847,795 Third party fee income .............................................. 1,182 330 1,058 294 2,191 1,512 6,083 7,435 Losses and loss adjustment expenses .................. 145,195 249,563 150,853 143,497 101,610 394,758 217,800 512,150 Acquisition costs ........................................................ 57,132 54,091 49,490 42,488 43,148 111,223 79,982 171,960 Other underwriting expenses .................................. 16,468 14,111 20,167 14,189 14,683 30,579 26,834 61,189 Underwriting income (loss) ...................................... $ 40,341 $ (59,074) $ 13,181 $ 23,671 $ 45,871 $ (18,732) $ 73,078 $ 109,931 Key Ratios: Attritional loss ratio - current year ........................... 54.2 % 51.8 % 51.7 % 51.0 % 50.5 % 53.0 % 54.3 % 52.7 % Attritional loss ratio - prior year development ....... 2.0 % (2.2) % (0.4) % 0.0 % (0.5) % (0.1) % 1.3 % 0.5 % Catastrophe loss ratio - current year ...................... 3.2 % 50.6 % 16.1 % 16.7 % 0.0 % 26.9 % 0.0 % 8.9 % Catastrophe loss ratio - prior year development .. (3.1) % (3.6) % (2.6) % (3.5) % 0.0 % (3.3) % 0.0 % (1.7) % Loss and loss adjustment expense ratio ............... 56.3 % 96.6 % 64.8 % 64.2 % 50.0 % 76.5 % 55.6 % 60.4 % Acquisition cost ratio ................................................. 22.1 % 20.9 % 21.3 % 19.0 % 21.2 % 21.5 % 20.4 % 20.3 % Other underwriting expense ratio ............................ 5.9 % 5.3 % 8.2 % 6.2 % 6.2 % 5.6 % 5.3 % 6.3 % Combined ratio .......................................................... 84.3 % 122.8 % 94.3 % 89.4 % 77.4 % 103.6 % 81.3 % 87.0 % Gross premiums written Property ...................................................................... $ 143,617 $ 223,077 $ 29,694 $ 68,560 $ 135,021 $ 366,694 $ 325,493 $ 423,747 Casualty ...................................................................... 182,005 179,534 141,594 128,891 123,498 361,539 254,226 524,711 Specialty ..................................................................... 41,605 70,736 22,170 30,425 33,169 112,342 113,069 165,664 Total .......................................................................... $ 367,227 $ 473,347 $ 193,458 $ 227,876 $ 291,688 $ 840,575 $ 692,788 $ 1,114,122 Net premiums earned Property ...................................................................... $ 80,313 $ 95,468 $ 78,113 $ 84,733 $ 73,864 $ 175,782 $ 145,598 $ 308,444 Casualty ...................................................................... 142,814 127,104 120,458 107,886 99,467 269,918 185,649 413,993 Specialty ..................................................................... 34,827 35,789 34,062 30,932 29,790 70,616 60,364 125,358 Total .......................................................................... $ 257,954 $ 258,361 $ 232,633 $ 223,551 $ 203,121 $ 516,316 $ 391,611 $ 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 $ 227.8 8.9 % Northeast U.S. Hurricane 1 in 100 208.8 8.2 % Gulf (TX - AL) U.S. Hurricane 1 in 100 170.4 6.7 % California Earthquake 1 in 250 286.2 11.2 % Pacific Northwest Earthquake 1 in 250 122.1 4.8 % (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 July 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 ................................................................... 30.2 % 23.6 % 22.0 % 26.9 % Adjustment for: ...................................................................................................................................................... Net realized (gains) losses on investments - Fixed maturity and short-term investments(1) .................... (0.2) % 0.3 % (0.1) % 0.4 % Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1) ................ (4.6) % 0.2 % (5.2) % 1.3 % Net foreign exchange (gains) losses ................................................................................................................. 0.7 % 0.3 % 0.6 % 0.4 % Operating return on average common shareholders' equity - annualized .................................................. 26.1 % 24.4 % 17.3 % 29.0 % Other Information Non-GAAP Measures Net income (loss) and other comprehensive income (loss) attributable to common shareholders per common share - diluted ...................................................................................................................................... $ 1.79 $ 1.20 $ 2.56 $ 2.57 Adjustment for: ..................................................................................................................................................... Net realized (gains) losses on investments - Fixed maturity and short-term investments(1) .................... (0.01) 0.01 (0.01) 0.04 Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1) ............... (0.27) 0.01 (0.60) 0.14 Net foreign exchange (gains) losses ................................................................................................................ 0.04 0.02 0.06 0.03 Operating income (loss) attributable to common shareholders per common share - diluted .................. $ 1.55 $ 1.24 $ 2.01 $ 2.78 Three Months Ended June 30, Six Months Ended June 30, ($ in thousands) 2025 2024 2025 2024 Net income (loss) and other comprehensive income (loss) attributable to common shareholders ........ $ 187,415 $ 131,085 $ 268,288 $ 288,259 Adjustment for: ...................................................................................................................................................... Net realized (gains) losses on investments - Fixed maturity and short-term investments(1) .................... (1,343) 1,411 (867) 4,352 Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1) ................ (28,782) 1,608 (63,269) 14,599 Net foreign exchange (gains) losses ................................................................................................................. 4,513 1,782 $ 7,039 $ 3,911 Operating income (loss) attributable to common shareholders .................................................................... $ 161,803 $ 135,886 $ 211,191 $ 311,121 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 June 30, Six Months Ended June 30, ($ in thousands) 2025 2024 2025 2024 Underwriting income (loss) .................................................................................................................................... $ 67,459 $ 65,299 $ 9,199 $ 97,825 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ........ 229,101 164,971 496,822 432,960 Net foreign exchange gains (losses) .................................................................................................................... (4,513) (1,782) (7,039) (3,911) Corporate expenses ............................................................................................................................................... (12,853) (16,262) (25,821) (27,764) Amortization of intangible assets .......................................................................................................................... (4,004) (3,317) (7,895) (6,569) Interest expense ...................................................................................................................................................... (4,729) (6,031) (10,331) (11,738) Income tax (expense) benefit ................................................................................................................................ (2,675) (2,496) (5,882) (3,089) Net income (loss), prior to non-controlling interest ............................................................................................ $ 267,786 $ 200,382 $ 449,053 $ 477,714 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 June 30, Six Months Ended June 30, ($ in thousands) 2025 2024 2025 2024 Third party fee income ............................................................................................................................................ $ 5,014 $ 5,989 $ 9,676 $ 13,470 Other income (loss), excluding third party fee income ...................................................................................... — — — — Other income (loss) ................................................................................................................................................. $ 5,014 $ 5,989 $ 9,676 $ 13,470

20 Three Months Ended June 30, Six Months Ended June 30, ($ in thousands) 2025 2024 2025 2024 Other underwriting expenses ................................................................................................................................ $ 55,975 $ 48,655 $ 105,709 $ 92,008 Corporate expenses ............................................................................................................................................... 12,853 16,262 25,821 27,764 General and administrative expenses ................................................................................................................. $ 68,828 $ 64,917 $ 131,530 $ 119,772 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. June 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 (the “Form 10-K”) 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 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 our strategic partnerships division; • our inability to control the allocations to, and/or the performance of, the Two Sigma Hamilton Fund, LLC (“Two Sigma Hamilton Fund” or “TSHF”) 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 Two Sigma 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; • 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 quarterly reports on Form 10-Q. 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 Entrepreneurial & 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 productive 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 Joining soon *Effective September 1, 2025. **Alex Baker is the Group Chief Risk Officer until he transitions to CEO of Hamilton Global Specialty effective September 1, 2025. Raymond Karrenbauer 25+ Years Group CIO Former: Cyber AB Joining in September Megan Graves 20+ Years CEO, Hamilton Re Retiring September 1, 2025 Venkat Krishnamoorthy 30+ Years (IT Industry) Group CTO Retiring August 30, 2025

6 $2.4B FY 2024 $1.6B 1H 2025 Gross Premiums Written (“GPW”) $149m FY 2024 $9m 1H 2025 Underwriting Income 91.3% FY 2024 99.1% 1H 2025 Combined Ratio Hamilton – Overview and Results Annual Segmental Results Group Financial Highlights $5.3B 2Q 2025 Cash & Invested Assets $2.6B 2Q 2025 Shareholders’ Equity $400m FY 2024 $268m 1H 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% 56% 66% 40% 38% 37% 36% 33% 32% 33% 111% 106% 103% 90% 91% 88% 99% 2020 2021 2022 2023 2024 1H 2024 1H 2025 $1,087 $1,447 $1,647 $1,951 $2,423 $1,325 $1,555 2020 2021 2022 2023 2024 1H 2024 1H 2025 Hamilton Group – Strategic Growth and Sustainable Underwriting Profitability Hamilton Group - Gross Premiums Written ($’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% 55% 46% 44% 43% 43% 39% 39% 40% 111% 108% 97% 95% 96% 94% 94% 2020 2021 2022 2023 2024 1H 2024 1H 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 $632 $715 2020 2021 2022 2023 2024 1H 2024 1H 2025 International Segment - Gross Premiums Written ($’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% 56% 77% 31% 29% 29% 28% 27% 26% 27% 111% 104% 110% 85% 87% 81% 104% 2020 2021 2022 2023 2024 1H 2024 1H 2025 $425 $554 $713 $846 $1,114 $693 $841 2020 2021 2022 2023 2024 1H 2024 1H 2025 Bermuda Segment - Gross Premiums Written ($’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 2Q 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 – $5.3 Billion Investment Portfolio as of June 30, 2025 Fixed Income, Short-Term and Cash 61.3% / $3.2B Two Sigma Hamilton Fund 38.7% / $2.1B *Investment management agreement (“IMA”).

16 Fixed Income Investment Portfolio as of June 30, 2025 49% 27% 12% 12% Corporate US Treasury US Agency Other $2.7B Corporate A2 US Treas. Aa1 US Agency Aa1 Other Aa1 Fixed income portfolio is managed by two external managers Fixed income investments of $2.7 billion – Average rating of Aa3, and duration of 3.4 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 fixed income, global equities, futures and FX markets Two Sigma Hamilton Fund $2.1B TSHF as of June 30, 2025 13.0% Average annualized returns 2014-2Q 2025 Dedicated- fund of one Allocation 70% equities 30% macro Highly liquid Investments TSHF Annual Returns Since 2018 Two Sigma Hamilton Fund, LLC (“TSHF”) 1.42 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 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