HG 10-K & 10-Q changes, risk factors and insider trading

Our business is subject to a number of risks, including risks that could prevent us from achieving our business objectives or financial goals or that otherwise could adversely affect our business, results of operations, financial condition and liquidity, that you should carefully consider. These risks are discussed more fully in “Risk Factors” below. These risks includeinclude, but may not necessarily be limited to, the following:

•challenges from competitors, including those arising from industry consolidationconsolidation, alternative capital and technological advancementsadvancements, including the increasing use of advanced analytics and AI;

•unpredictable catastrophicevents, events,including natural catastrophes and man‑made disasters, global climate change and/or emerging claimclaim, litigation and coverage issues that may increase loss severity or expand coverage obligations;

•our ability, or thosethat of the third parties on which we rely, to ensure reserves are adequate to cover actual losses and to accurately evaluateassess underwriting risk, models, assessmentsassumptions, data quality and/or the pricing of risksrisks, particularly in long‑tail, low‑frequency or emerging lines of business;

•our ability to defend and protect our intellectual property rights, including our proprietary technology platforms,platforms and data, to comply with our obligations under our license and technology agreements or to licenseobtain rightsor renew licenses to technology or data on reasonable terms;

•the impact of risks associated with human error, misconduct or fraud, model uncertainties,uncertainty, cybersecurity threats such as cyber-attackscyber‑attacks and security breachesbreaches, misuse of AI and our reliance on third-partythird‑party ITinformation technology systems that canmay failfail, be disrupted or needrequire replacement;

•our ability to secure necessary credit facilities, or additional typesletters of credit,credit or other forms of financing or collateral on favorable terms or at all;

•our limited financial and operatingoperational flexibility due to thecovenants covenantsand other restrictions in our existing or future credit facilities and debt arrangements;

•our exposure to the credit risk of theinsurance and reinsurance intermediaries on which we rely for the collection of premiums and payment of claims;

•our failure to pay claims in a timely mannermanner, significant reserve strengthening, or the need to sell investments under unfavorable market or other conditions in order to meet liquidity requirements;

•downgrades, potential downgrades or other negative actions by rating agenciesagencies, including changes in rating agency methodologies;

•our ability to manage risks associated with adverse macroeconomic conditions resulting fromconditions, geopolitical instability and global economic events, including current or anticipated military conflicts, public health crises, terrorism, sanctions, inflation, rising interest rates, energy prices,price inflation and interest ratesvolatility and other global eventsdisruptions;

•the cyclical nature of the insurance and reinsurance business, which may causeresult thein declines in pricing and more competitive terms forand our products to declineconditions;

•our results of operations potentially fluctuating significantly from period to period and not being indicative of our long-termlong‑term prospects;

•our ability to execute our strategy and to modifyadapt our business and strategic planplans withoutin shareholderresponse approvalto changing market, regulatory and competitive conditions;

•our dependence on key executives,executives and other personnel, including the potential loss of Bermudian or other critical personnel, and our ability to attract and retain qualified personnel, particularlyemployees in veryhighly competitive hiringlabor conditionsmarkets;

•foreign operational riskrisks, such asincluding foreign currency riskrisk, political instability, regulatory uncertainty and politicaldiffering risklegal regimes in jurisdictions where we operate;

•our ability to identifyidentify, execute and executeintegrate opportunitiesgrowth foropportunities, growth,including acquisitions or other strategic transactions, and to complete transactions as planned or realize the anticipated benefits of anysuch acquisitions or other investmentsinitiatives;

•risks arising from our management of alternative reinsurance platforms onand behalfvehicles offor third‑party investors in entities managed by Hamilton Strategic Partnerships;

•our inability to control the allocationsasset to,allocation, and/investment decisions or the performance of,of the TS Hamilton Fund investment portfolio and our limited ability to withdraw our capital accountsfrom the TS Hamilton Fund;

•the impact of risks from conflicts of interestinterest, amonggovernance, operational or regulatory risks involving Two Sigma, the ManagingTS Member,Hamilton TwoFund Sigma andor their respective affiliates affectingthat could adversely affect investment performance or our business;

•the historical performance of Two Sigma or the TS Hamilton Fund not being indicative of the future resultsperformance of the TS Hamilton Fund’s investment portfolio and/or of our future results;

•the impacts of risks associated with our investment strategy, including thatthe suchuse risksof areleverage, derivatives, illiquid assets and concentration risk, which may be greater than those faced by some of our competitors;

•our potentially becoming subject to additional or increased taxation, including U.S. federal income taxation,tax, Bermuda taxationtax or other taxestaxes, as a result of achanges change ofin tax lawslaws, interpretations or otherwiseour operations;

•the potential classification of us or our potentiallysubsidiaries as a passive foreign investment company or becoming subject to U.S. withholding and information reporting requirements under FATCA provisions;

•our ability to compete effectively in a heavilyhighly regulated industry in light of new or changing domestic or international laws and regulations, including accounting practices,standards and theevolving impact of newregulatory interpretations of current laws and regulations;

•the suspensionsuspension, limitation or revocation of licenses or approvals required by our subsidiaries’ insurance licensesand reinsurance subsidiaries;

•significant legal, governmentalregulatory or regulatorygovernmental proceedings or investigations;

•restrictions on our insurance and reinsurance subsidiaries’ ability to pay dividends andor make other distributions to us being restricted by law;

•the limited ability of investors to influence corporate matters due to our multiple multi‑class common share structure and the voting provisions ofin our Bye-lawsBye‑laws;

•the risk that anti-takeoveranti‑takeover provisions in our Bye-lawsBye‑laws or Bermuda law could discourage, delay,delay or prevent a change in control, even if the change in control would be beneficial to our shareholders; and

•the difficulties investors may face in enforcing judgments or protecting their interests and serving process or enforcing judgments against us inor theour United States;directors and officers.

CompetitionWe and consolidationoperate in thea highly competitive insurance and reinsurance industryenvironment couldthat adverselycontinues impactto us.evolve Weand competeconsolidate. withOur competitors include major U.S. and non-U.S. insurers and reinsurers, somemany of which havepossess greater financial, marketingdistribution and management resourcesresources, higher financial strength ratings, broader product offerings and longer operating histories than we do. In addition, pension funds, endowments, investment banks, investment managers, hedge funds and other capital markets participants have been active inentered the insurance and reinsurance market, eithermarket through the formation of insurance and reinsurance companies or thethrough usealternative ofrisk othertransfer financialstructures products intendeddesigned to compete with traditional insurance and reinsurance.products. We may also face competition from non-traditional competitors, as well as start-up companiesentrants and othersstart-ups seeking access to thisdisrupt industry.the industry and capture market share.

We devote significant focus, attention and resources to assess the risks related to our businesses as accurately as we can. We establish losses and loss adjustment expenses,expenses or LAE,("LAE"), reserves for the best estimate of the ultimate payment of all claims that have been incurred, or could be incurred in the future, and the related costs of adjusting those claims, as of the date of our financial statements. These valuesestimates are unknowninherently withinuncertain and subject to numerous variables, including claims inflation, frequency and severity trends, judicial and legislative developments, economic conditions, social inflation and evolving claims practices. The estimation of loss reserves is more difficult during times of adverse economic and market conditions due to unexpected changes in behavior of claimants and policyholders, including an increase in fraudulent reporting of exposures and/or losses, reduced maintenance of insured properties or increased frequency of small claims. Actual losses may differ, possibly materially, from our industry, so these items within our financial statements are always based on estimates, and our ultimate liability will almost certainly be greater, or less than, our estimate.estimates.

The following discussion and analysis should be read in conjunction with the "Selected Consolidated Financial Data" and our audited consolidated financial statements and related notes thereto included in the Group's Annual Report on Form 10-K (the"Annual Report" or "Form 10-K"). In addition to historical information, this discussion contains forward-looking statements that involve risks, uncertainties and assumptions that could cause actual results to differ materially from management’s expectations. Factors that could cause such differences are discussed in the sections entitled "Special Note Regarding Forward-Looking Statements" and "Risk Factors" in the Form 10-K. We do not undertake any obligation to update any forward-looking statements or other statements we may make in the following discussion or elsewhere in this document even though these statements may be affected by events or circumstances occurring after the forward-looking statements or other statements were made.

WeHamilton areInsurance Group, Ltd. ("Hamilton", "Hamilton Group", the "Group" or the "Company") is a global specialty insurance and reinsurance company founded in Bermuda in 2013, enhanced by data and technology, focused on producing sustainable underwriting profitability and delivering significant shareholder value. We intend to continue growing our diverse book of business by responding to changing market conditions, prudently managing our capital, and driving sustainable shareholder returns.

•Hamilton Global Specialty focuses predominantly on commercial specialty and casualty insurance for medium to large-sized accounts and specialty reinsurance products written by Lloyd’s Syndicate 4000 and HIDAC.Hamilton Insurance DAC ("HIDAC"). Syndicate 4000, a leading Lloyd’s syndicate, generates a significant portion of premium from the U.S. Excess & Surplus ("E&S") market and has ranked among the most profitable and least volatile syndicates at Lloyd’s over the last 10 years.

We seek to prudently manage our capital with the objective of effectively navigating different market conditions and generating strong underwriting margins throughout all market cycles. Our scaled and diversified platforms and product offerings, and our broad industry relationships provide significant opportunity to underwrite our chosen classes of property, casualty and specialty insurance and reinsurance as market opportunities arise. Leveraging our disciplined underwriting approach, balance sheet strength and flexibilityflexibility, and real-time technology prowess, we can respond dynamically to capture opportunities as markets evolve.

We see continued growth opportunities in both the insurance and reinsurance markets in which we operate and intend to pursue disciplined growth across our underwriting platforms. In recent years the E&S market has benefited from a strong rate environment and increased submissions as business has shifted into the non-admitted market from the admitted market. Non-admitted insurers are able to cover unique and hard-to-place risks because they have flexibility of rate and form and can accommodate the unique needs of insureds who are unable to obtain coverage from admitted carriers. We believe the access our three underwriting platforms have to U.S. E&S insurance business will allowallows us to build a robust and diversified book of business and achieve our profitable growth objectives throughout various market cycles.

Our strong, sustainable underwriting operations are complemented by our unique investment portfolio, which consists of the Two Sigma Hamilton Fund, LLC ("TS Hamilton Fund" or "TSHF"), and our investment grade fixed income portfolio, which is currently benefiting from strongfavorable interest rates. We plan towill continue to optimize our investment portfolio through a balanced allocation of invested assets and maintain the flexibility to adjust this allocation as needed. We believe our strategy of disciplined underwriting growth, balanced with our investment platform, will drive our ability to create shareholder value.

We have a unique and long-term investment management relationship with Two Sigma. Founded in 2001, Two Sigma is a premier investment manager with a strong track record, driven by a differentiated application of technology and data science. The TS Hamilton Fund is a dedicated fund-of-onefund of one managed by Two Sigma with exposures to certain Two Sigma macroequity and equitymacro strategies and is designed to provide low-correlated absolute returns, primarily by combining multiple hedged and leveraged systematic and non-systematic investment strategies with proprietary risk management investment optimization and execution techniques. The TS Hamilton Fund invests in a broad set of financial instruments and is primarily focused on liquid strategies in global equity, FX markets, exchange-listed and over the counter options (and their underlying instruments) and other derivatives. This liquidity profile fits well with our business, while also providing the benefit of access to a dedicated fund-of-one.fund of one.

Two Sigma has broad discretion to allocate invested assets to different opportunities. AtIts December 31, 2024, itscurrent investments include Two Sigma Spectrum Portfolio, LLC ("STV"), Two Sigma Equity Spectrum Portfolio, LLC ("ESTV"), Two Sigma Absolute Return Portfolio, LLC ("ATV"), Two Sigma Futures Portfolio, LLC ("FTV"), Two Sigma SpectrumHorizon Portfolio, LLC ("STVHTV"), Two Sigma Navigator Portfolio, LLC ("NTV") and Two Sigma Equity SpectrumKuiper Portfolio, LLC ("ESTVKTV"). The TS Hamilton Fund’s trading and investment activities are not limited to these strategies and techniques and the TS Hamilton Fund is permitted to pursue any investment strategy and/or technique that Two Sigma determines in its sole discretion to be appropriate for the TS Hamilton Fund from time to time.

On December 27, 2023, the Bermuda Government enacted a 15% corporate income tax that generally became effective for Bermuda domiciled entities on or after January 1, 2025. The legislation defers the effective date until January 1, 2030 for so long as the consolidated group operates in six or fewer jurisdictions, has less than €50 million in tangible assets and none of its Bermuda entities are subject to the Income Inclusion Rule in any other jurisdiction.jurisdiction ("Limited International Footprint Exemption"). The act is a response to the Organization of Economic Cooperation and Development ("OECD") Pillar 2Two worldwideinitiative minimumas taxenacted thatby wouldthe otherwiseU.K. and Ireland in their respective domestic laws. In substance, these laws require a top-up tax be paid on Bermuda-sourced income to non-Bermuda jurisdictions such that a 15% minimum effective tax rate ("ETR") is achieved for Hamilton Group’s Bermuda entities.entities, the Undertaxed Profits Rule ("UTPR"). Hamilton Group expects to be exempt from the worldwide minimum taxUTPR until January 1, 2030, pursuant to an exemption similar to that available in Bermuda. The actBermuda legislation includes a provision referred to as the economicEconomic transitionTransition adjustmentAdjustment (“"ETA”"), which iswill intendedreduce tofuture provideyears' aBermuda fairtaxable and equitable transition into the tax regime.income. As of December 31, 2024,2025, the Company holds a deferred tax asset of $35.4 million on its balance sheet related to the ETA.

On January 15, 2025, the OECD issued additional guidance related to the calculation of income subject to taxation under the Pillar 2.Two initiative. Specifically, it provided that for purposes of calculating Pillarthe 2 taxes,UTPR, a deduction for the ETA will not be allowed in years after 2026. Accordingly, when Hamilton Group becomes subject to Pillarthe 2 taxation on its Bermuda earnings,UTPR, expected in 2030, it is possible that a top-up tax liability will arise to the extent that it does not achieve a 15% minimum ETR on its Bermuda taxable earnings, excluding the ETA deduction. If Hamilton were to incur a Pillar 2UTPR top-up tax on its Bermuda earnings, the liability would be recorded in the period and jurisdiction in which it is incurred.

(2) Third party fee income is a non-GAAP financial measure as defined in Item 10(e) of SEC Regulation S-K. The reconciliation to other income (loss), the most comparable GAAP financial measure, also included other income (loss), excluding third party fee income of $Nil, $Nil, $0.4 millionmillion, and $(0.3) million for each of the years ended December 31, 2025, 2024, 2023 and 2022, respectively, and less than $0.1 million for each of the yearsyear ended November 30, 2021 and 2020.2021. Refer to 'Management’s Discussion and Analysis of Financial Condition and Results of Operations—Non-GAAP Measures' for further details.

(3) Other underwriting expenses is a non-GAAP financial measure as defined in Item 10(e) of SEC Regulation S-K. The reconciliation to general and administrative expenses, the most comparable GAAP financial measure, also included corporate expenses of $57.2 million, $61.1 million, $76.7 million, $20.1 million,million and $22.5 million and $22.9 million for the years ended December 31, 2025, 2024, 2023 and 2022, and November 30, 2021 and 2020,2021, respectively. Refer to 'Management’s Discussion and Analysis of Financial Condition and Results of Operations—Non-GAAP Measures' for further details.

IBNR estimates are necessary due to the potential development on reported claims and the reporting time lag between when a loss event occurs and when it is actually reported (the "reporting lag"). Reporting lags may arise from a number of factors, including but not limited to the nature of the loss, the use of intermediaries and the complexity of the claims adjusting process. The lack of specific information means the Company must make estimates. IBNR is calculated by deducting incurred losses (i.e. paid losses and case reserves) from management’s best estimate of the ultimate losses. Unlike case reserves, which are established at the claim or contract level, IBNR reserves are generally established at an aggregate level and cannot be identified as reserves for a particular loss event or contract.

•Bornhuetter-Ferguson method: The Bornhuetter-Ferguson method uses as a starting point an assumed IELR and blends in the loss ratio, which is implied by the claims experience to date using historical or benchmark loss development patterns on paid claims data or reported claims data. Although the method tends to provide less volatile indications at early stages of development and reflects changes in the external environment, it can be slow to react to emerging loss development and may, if the IELR proves to be inaccurate, produce loss estimates which take longer to converge with the final settlement value of loss; and

The Company’s recorded reserves at each reporting date reflect management’s best estimate of the ultimate reserve for losses and loss adjustment expenses at that date. Management completes quarterly reserve studies for each exposure group for its International and Bermuda segments. Management analyzes significant variances between internal and external actuarial estimates, as well as any relevant additional market, underwriting or claims data that may be available and relevant for setting management’s best estimate of ultimate reserves. As a result of these considerations, the selected reserve estimate may be higher or lower than the indicated external actuarial indicated estimate.

In December 2023, Hamilton Group sponsored a new industry loss index-triggered catastrophe bond through the issuance of Series 2024-1 Class A Principal-at-Risk Variable Rate Notes by Bermuda-domiciledBermuda domiciled Easton Re Ltd. ("Easton Re"), which provide the Company's operating platforms with multi-year risk transfer capacity of $200 million to protect against named storm risk in the United States and earthquake risk in the United States and Canada. The risk period for Easton Re is from January 1, 2024 to December 31, 2026.

(1) Third party fee income is a non-GAAP financial measure as defined in Item 10(e) of SEC Regulation S-K. The reconciliation to other income (loss), the most comparable GAAP financial measure, also included other income (loss), excluding third party fee income of $Nil, $0.4 million and $(0.3) million$Nil for each of the years ended December 31, 2024, 20232025 and 2022,2024 respectively.and $0.4 million for the year ended December 31, 2023. Refer to 'Management’s Discussion and Analysis of Financial Condition and Results of Operations— – Non-GAAP Measures' for further details.

(2) Other underwriting expenses is a non-GAAP financial measure as defined in Item 10(e) of SEC Regulation S-K. The reconciliation to general and administrative expenses, the most directly comparable GAAP financial measure, also included corporate expenses of $61.1$57.2 million, $76.7$61.1 million, and $20.1$76.7 million for the years ended December 31, 2024,2025, 20232024 and 2022,2023, respectively. Refer to 'Management’s Discussion and Analysis of Financial Condition and Results of Operations—Non-GAAP Measures' for further details.

(3) Underwriting income (loss) is a non-GAAP financial measure as defined in Item 10(e) of SEC Regulation S-K. Refer to 'Management’s Discussion and Analysis of Financial Condition and Results of Operations— – Non-GAAP Measures' for further details.

Gross premiums written Gross premiums written were $2.4$2.9 billion, $2.0$2.4 billion and $1.6$2.0 billion for the years ended December 31, 2024,2025, 20232024 and 2022,2023, respectively. The increase in gross premiums written for the year ended December 31, 2025 compared to the year ended December 31, 2024 was primarily driven by our casualty reinsurance classes and casualty, specialty and property insurance classes. The increase was as a result of growth in both new and existing business. The increase in gross premiums written for the year ended December 31, 2024 compared to the year ended December 31, 2023 was primarily driven by our casualty reinsurance, property reinsurance, specialty reinsurance and casualty insurance business. The growth was a result of new business, increased participations on existing business and a strong rate environment across multiple classes of business. The increase in gross premiums written for the year ended December 31, 2023 compared to the year ended December 31, 2022 was primarily driven by expansion into additional classes, notably casualty reinsurance and specialty insurance, increased participation on existing business and rate increases across multiple classes of business.

Underwriting results The combined ratio was 91.3%92.9% and 90.1%91.3% for the years ended December 31, 20242025 and 2023,2024, respectively. The modestincrease was primarily driven by an increase in the catastrophe loss ratio and the acquisition cost ratio, partially offset by a decrease in the attritional loss ratio and other underwriting expense ratio. The increase in the combined ratio from 90.1% for the year ended December 31, 2023 to 91.3% for the year ended December 31, 2024 was driven by an increase in the catastrophe loss ratio and attritional loss ratio, partially offset by a decrease in the other underwriting expense ratio and acquisition cost ratio. The decrease in the combined ratio from 102.8% for the year ended December 31, 2022 to 90.1% for the year ended December 31, 2023 was driven by lower catastrophe losses as described further below under Losses and Loss Adjustment Expenses.

Catastrophe losses - current and prior year development were $87.6$159.0 million, $36.9$87.6 million and $168.9$36.9 million for the years ended December 31, 2024,2025, 20232024 and 2022,2023, respectively. Catastrophe losses for the year ended December 31, 2025 were driven by the California wildfires ($159.7 million), severe convective storms ($10.9 million) and the Queensland hailstorms ($6.9 million), partially offset by favorable prior year development of $18.5 million. Catastrophe losses for the year ended December 31, 2024 were driven by Hurricane Helene ($52.6 million), Hurricane Milton ($37.8 million), the Calgary hailstorms ($12.9 million), and Hurricane Debby ($5.6 million), partially offset by favorable prior year development of $21.3 million. Catastrophe losses for the year ended December 31, 2023 were driven by the Hawaii wildfires ($12.0 million), the wind and thunderstorm events which impacted states in both the Southern and Midwest U.S. during March 2023 ($11.0 million), severe convective storms in June 2023 ($7.6 million), Hurricane Idalia ($6.5 million), and the Vermont floods ($5.0 million), partially offset by favorable prior year development of $5.2 million. Catastrophe losses - current and prior year development for the year ended December 31, 2022 were driven by the Ukraine conflict ($79.6 million), Hurricane Ian ($77.5 million), Australian East Coast floods ($16.6 million), KwaZulu-Natal floods ($8.3 million), and Typhoon Nanmadol ($4.3 million), partially offset by favorable prior year development of $17.4 million.

Net investment income, net of non-controlling interest - TSHF, returned income of $274.5$300.9 million, $122.1$274.5 million and $77.2$122.1 million for the years ended December 31, 2024,2025, 20232024 and 2022,2023, respectively. This includes the fund's returns, net of investment management fees and performance incentive allocations. The aggregate incentive allocation to which the investment manager is entitled is included in "Net income (loss) attributable to non-controlling interestsinterest" in our GAAP financial statements.

Total net realized and unrealized gains (losses) on investments and net investment income (loss) - other returned income of $210.9 million, $87.5 million and $96.4 million and a loss of $73.4 million for the years ended December 31, 2024,2025, 20232024 and 2022,2023, respectively. Income for the year ended December 31, 2025 was primarily driven by investment income on a larger portfolio of higher yielding assets and positive mark-to-market returns. During the year ended December 31, 2024, the fixed maturity securities trading portfolio produced positive returns as the result of investment yield, partially offset by unrealized losses, primarily arising from U.S. treasuryTreasury interest rate increases. During the year ended December 31, 2023, the fixed maturity securities trading portfolio produced positive returns as the rate of rising interest rates slowed and reinvested funds generated higher yields. During the year ended December 31, 2022, the negative mark-to-market impact of rising U.S. treasury interest rates and other macroeconomic factors offset investment yield, giving rise to non-credit related net investment losses.

The CODM evaluates reportable segment performance based on the segment'ssegments' respective underwriting income or loss. Underwriting income or loss is calculated as net premiums earned less losses and loss adjustment expenses, acquisition costs, and other underwriting expenses, net of third party fee income. General and administrative expenses not incurred by the reportable segments are included in corporate and other expenses as part of the reconciliation of net underwriting income or loss to net income or loss attributable to common shareholders. As we do not manage our assets by reportable segment, investment income and assets are not allocated to reportable segments.

Corporate includes net realized and unrealized gains (losses) on investments, net investment income (loss), other income (loss) not incurred by the reportable segments, net foreign exchange gains (losses), general and administrative expenses not incurred by the reportable segments, impairment of goodwill, amortization of intangible assets, interest expense, and income tax expense (benefit).

Third party fee income decreased by $1.7$4.3 millionmillion, or 15.3%,26.3%, from $11.4$16.3 million for the year ended December 31, 20222024 to $9.7$12.0 million for the year ended December 31, 2023.2025. The decrease was primarily drivendue byto a reductiondecrease in syndicate management fees. Effective July 1, 2025, the numbermanagement of the third party syndicate was novated from Hamilton Managing Agency to another Lloyd's managing agency. This ended the Company's management of third party syndicates under management and the discontinuation of certain consortium arrangements.syndicates.

Attritional loss ratio - current year for the year ended December 31, 2024 was 53.5% compared to 53.2% for the year ended December 31, 2023, an increase of 0.3 percentage points. The increase wasincluded primarilya drivenspecific bylarge lossesloss of $11.8 million, or 1.3 points,million arising from the Baltimore Bridge collapse.

Attritional loss ratio - prior year for the year ended December 31, 2024 was a favorable 0.4% compared to a favorable 3.5% for the year ended December 31, 2023, an increase of 3.1 percentage points. TheWe experienced favorable attritional loss ratio - prior year development for the year ended December 31, 2024 wasof $3.4 million, primarily driven by favorable development in our property insurance and reinsurance classes, partially offset by unfavorable development in specialty insurance classes, impacted by two large losses, and casualty insurance, impacted by one specific large loss. In addition, casualty business protected by the LPT discussed in Note 7, Reinsurance, benefited from favorable development in the underlying reserves of $15.3 million, which was partially offset by a change in the deferred gain of $9.4 million, for a total net positive earnings impact of $5.9 million.

Catastrophe losses - current year and prior year ofwere $26.7 million and $12.6 million for the years ended December 31, 2024 and 2023, respectively. Catastrophe losses for the year ended December 31, 2024 were driven by Hurricane Helene ($19.6 million), Hurricane Milton ($12.8 million), and Hurricane Debby ($1.5 million), partially offset by favorable prior year development of $7.2 million. Catastrophe losses - current year and prior year of $12.6 million for the year ended December 31, 2023 were driven by the Vermont floods ($4.5 million), Hurricane Idalia ($2.9 million), Hawaii wildfires ($2.8 million), and other wind events ($0.5 million), in addition to unfavorable prior year development of $1.9 million.

The acquisition cost ratio for the year ended December 31, 20232025 was 26.5%26.2%, compared to 27.4%24.5% for the year ended December 31, 2022,2024, aan decreaseincrease of 0.91.7 percentage points. The decreaseincrease was primarily driven by casualty insurance classes and specialty reinsurance classes, primarily due to higher volumesprofit commission costs on certain lines of business writtenand a change in casualty insurance and property insurance classes that benefit from favorable overriding commission offset or lower acquisition costs, and other changes in the business mix.

The following discussion and analysis should be read in conjunction with the "Selected Consolidated Financial Data" and our audited consolidated financial statements and related notes thereto included in the Group's Annual Report on Form 10-K for the year ended December 31, 2025 (the "Form 10-K"). In addition to historical information, this discussion contains forward-looking statements that involve risks, uncertainties and assumptions that could cause actual results to differ materially from management’s expectations. Factors that could cause such differences are discussed in the sections entitled "Special Note Regarding Forward-Looking Statements" and "Risk Factors" in this Quarterly Report on Form 10-Q, as well as in "Risk Factors" in the Company's most recently filed Annual Report on Form 10-K.10-K and subsequent Quarterly Reports on Form 10-Q, including this Quarterly Report. We do not undertake any obligation to update any forward-looking statements or other statements we may make in the following discussion or elsewhere in this document even though these statements may be affected by events or circumstances occurring after the forward-looking statements or other statements were made.

Hamilton Insurance Group, Ltd. ("HamiltonHamilton,", "Hamilton GroupGroup,", the "GroupGroup," or the "CompanyCompany," "we," "us", or "our") is a global specialty insurance and reinsurance company founded in Bermuda in 2013, enhanced by data and technology, focused on producing sustainable underwriting profitability and delivering significant shareholder value. We intend to continue thoughtfully growing our diverse book of business by responding to changing market conditions, prudently managing our capital, and driving sustainable shareholder returns.

We harness multiple drivers to create shareholder value, including diverse underwriting operations supported by proprietary technology and a team of over 600 full-time employees, a strong balance sheet, and a unique investment management relationship with Two Sigma.Sigma Investments, LP ("Two Sigma"). We operate globally, with underwriting operations in London, Dublin, Bermuda and across the United States.

•Hamilton Select, our U.S. domestic E&S carrier, writes casualty and property insurance for smallsmall-to-medium toenterprise mid-sizedand lower middle market sized clients in the hard-to-place niche of the U.S. E&S market. We believe it presents meaningful and profitable growth opportunities in the near-to-long term, further expanding our footprint in the U.S. E&S market.

One of our key strategic priorities is sustainable underwriting profitability across theour business we write.portfolio. Our data-driven and disciplined underwriting processes position us to intelligently price and structure our products and risks across our business portfolio.business. We maintain trusted and long-standing relationships with our clients and brokers, who we believe will continue to provide us with increased access to attractive business.

We see continued growth opportunities in both the insurance and reinsurance markets in which we operate and intend to pursue disciplined growth across our underwriting platforms. In recent yearsyears, the E&S market has benefited from a strong rate environment and increased submissions as business has shifted into the non-admitted market from the admitted market. While growth in the E&S market is slowing down,slowing, non-admitted insurers are able to cover unique and hard-to-place risks because they have flexibility of rate and form and can accommodate the unique needs of insureds who are unable to obtain coverage from admitted carriers. We believe the access our three underwriting platforms have to U.S. E&S insurance business allows us to build a robust and diversified book of business and achieve our profitable growth objectives throughout variousall market cycles.cycles and, specifically for Hamilton Select, we look forward to increased opportunities we expect to see as a result of the platform's AM Best rating upgrade to "A" from "A-" on May 12, 2026.

In recent years, reinsurance business experienced a supply/demand imbalance in a number of classes, which created strong market conditions. This, combined with our relatively recent AM Best "A" rating upgrade, allowed us to accelerate growth opportunities in these areas. We have observed a change in the supply/demandtrading dynamicsenvironment in someseveral insurance and reinsurance classes in recent months, particularly property and some specialty classes, which is creating more competitive market conditions. However, we believe pricing is still risk adequate or better, at the portfolio level, in mostall areas.of the lines of business we write. Strong underlying market conditions persist in casualty classes, due to continued uncertainty around social inflation. We will continue to monitor the trading environment closely and use effective reinsurance protection to manage our net positions.

Our strong, sustainable underwriting operations are complemented by our unique investment portfolio, which consists of the Two Sigma Hamilton Fund, LLC ("TS Hamilton Fund" or "TSHF"), and our investment grade fixed income portfolio, which is currently benefiting from favorable interest rates.portfolio. We will continue to optimize our investment portfolio through a balanced allocation of invested assets and maintain the flexibility to adjust this allocation as needed. We believe our strategy of disciplined underwriting growth, balanced with our investment platform, will drive our ability to create shareholder value.

On December 27, 2023, the Bermuda Government enacted a 15% corporate income tax that generally became effective for Bermuda domiciled entities on or after January 1, 2025. The legislation defers the effective date until January 1, 2030 for so long as the consolidated group operates in six or fewer jurisdictions, has less than €50 million in tangible assets and none of its Bermuda entities are subject to the Income Inclusion Rule in any other jurisdiction ("Limited International Footprint Exemption"). The act is a response to the Organization of Economic Cooperation and Development ("OECD") Pillar Two initiative as enacted by the U.K. and Ireland in their respective domestic laws. In substance, these laws require a top-up tax be paid on Bermuda-sourced income to non-Bermuda jurisdictions such that a 15% minimum effective tax rate ("ETR") is achieved for Hamilton Group’s Bermuda entities, the Undertaxed Profits Rule ("UTPR"). Hamilton Group expects to be exempt from the UTPR until January 1, 2030, pursuant to an exemption similar to that available in Bermuda. The Bermuda legislation includes a provision referred to as the Economic Transition Adjustment ("ETA"), which will reduce future years' Bermuda taxable income. As of MarchJune 31,30, 2026, the Company holds a deferred tax asset of $35.4 million on its balance sheet related to the ETA.

(2) Other underwriting expenses is a non-GAAP financial measure as defined in Item 10(e) of SEC Regulation S-K. The reconciliation to general and administrative expenses, the most directly comparable GAAP financial measure, also included corporate expenses of $11.1$13.0 million and $13.0$12.9 million for the three months ended MarchJune 31,30, 2026 and 2025, respectively. Refer to 'Management’s Discussion and Analysis of Financial Condition and Results of Operations – Non-GAAP Measures' for further details.

The following significant items impacted the consolidated results of operations for the three months ended MarchJune 31,30, 2026 and 2025:

Gross premiums written Gross premiums written were $940.1$831.0 million and $843.3$712.0 million for the three months ended MarchJune 31,30, 2026 and 2025, respectively. The increase in gross premiums written was primarily driven by our casualty reinsurance and insurance classes and specialty insurance and reinsurance classes as a result of growth in both new and existing business, partially offset by a decrease in our property reinsurance classesand insurance classes, primarily as a result of lowerrate reinstatement premiumsdecreases for the threecurrent months ended March 31, 2026.quarter.

Underwriting results The combined ratio was 89.8%95.0% and 111.6%86.8% for the three months ended MarchJune 31,30, 2026 and 2025, respectively. The decreaseincrease was primarily driven by aan decreaseincrease in the catastrophe loss ratio and otheracquisition underwriting expensecost ratio, partially offset by ana increasedecrease in the attritionalother lossunderwriting ratio and acquisition costexpense ratio.

Attritional loss ratio - current year for the three months ended MarchJune 31,30, 2026 was 54.5%53.3% compared to 51.9%53.0% for the three months ended MarchJune 31,30, 2025, an increase of 2.60.3 percentage points. The increase was primarily driven by a change in business mix, including more casualty reinsurance and specialty insurance business.

Attritional loss ratio - prior year for the three months ended MarchJune 31,30, 2026 was ana unfavorablefavorable 2.4%0.1% compared to a favorable 2.9%0.5% for the three months ended MarchJune 31,30, 2025, an increase of 5.30.4 percentage points. The attritional loss ratio - prior year for the three months ended MarchJune 31,30, 2026 was primarily driven by additional loss information in relation to the Baltimore Bridge collapse. In addition, casualty business protected by the loss portfolio transfer ("LPT") discussed in Note 6, Reinsurance, benefited from favorable development in theboth underlyingour reserves of $0.1 millionInternational and aBermuda changeproperty classes and our International specialty and casualty classes, partially offset by unfavorable development in thecertain deferredBermuda gaincasualty of $0.2 million, for a total net positive earnings impact of $0.3 million.classes. The attritional loss ratio - prior year for the three months ended MarchJune 31,30, 2025 was primarily driven by favorable development in both our InternationalBermuda and BermudaInternational property and specialty and property classes. In addition, casualty business protected by the LPT benefited from favorable development in the underlying reserves of $1.0 million, which wasclasses, partially offset by aunfavorable changedevelopment in thecertain deferredBermuda gaincasualty of $0.5 million, for a total net positive earnings impact of $0.5 million.classes.

Catastrophe losses - current year and prior year development were $Nil$49.9 million and $1.5 million for the three months ended MarchJune 31,30, 2026.2026 and 2025, respectively. Catastrophe losses for the three months ended MarchJune 31,30, 2026 were driven by the Middle East conflict ($45.7 million), in addition to unfavorable prior year development of $4.2 million. Catastrophe losses for the three months ended June 30, 2025 were asdriven aby resultsevere ofconvective thestorms California($9.9 wildfires of $159.7 million,million), partially offset by favorable prior year development of $9.2$8.4 million.

(1) Prior to non-controlling interest performance incentive allocation Total net realized and unrealized gains (losses) on investments and net investment income (loss) - TSHF, prior to non-controlling interest, returned income of $176.6$226.5 million and $204.0$167.5 million for the three months ended MarchJune 31,30, 2026 and 2025, respectively. This includes the fund's returns, net of investment management fees.

Net investment income, net of non-controlling interest - TSHF, returned income of $93.1$115.5 million and $103.6$87.1 million for the three months ended MarchJune 31,30, 2026 and 2025, respectively. This includes the fund's returns, net of investment management fees and performance incentive allocations. The aggregate incentive allocation to which the investment manager is entitled is included in "Net income (loss) attributable to non-controlling interest" in our GAAP financial statements.

TS Hamilton Fund produced returns, net of investment management fees and performance incentive allocations, of 4.3%5.1% and 5.5%4.4% for the three months ended MarchJune 31,30, 2026 and 2025, respectively.

For the three months ended MarchJune 31,30, 2026, TS Hamilton Fund experienced gains infrom single name equities trading within the equity market neutral vehicles STV, ESTV,ESTV and ATV. Gains infrom single name equities trading were led by the U.S., followed by China onshore and Europe.East Asia. TS Hamilton Fund also experienced gains from macro trading within the systematic macro vehicle, FTV, the relative value macro vehicle, HTV, and the scientificrelative discretionaryvalue macrorates vehicle, NTV.KTV. Gains infrom macro trading were led by commoditiesequities in FTV.FTV Gains in TS Hamilton Fundand were partially offset by losses from macro trading within the relativescientific valuediscretionary ratesmacro vehicle, KTV.NTV.

For the three months ended MarchJune 31,30, 2025, TS Hamilton Fund experienced gains infrom single name equities trading within the equity market neutral vehicles STV, ESTV,ESTV and ATV. Gains infrom single name equities trading were led by the U.S., followed by EastEurope. Asia.Gains in TS Hamilton Fund alsowere experiencedpartially gainsoffset by losses from macro trading within the systematic macro vehicle, FTV, the relative value macro vehicle, HTV, the scientific discretionary macro vehicle, NTV, and the relative value rates vehicle, KTV. GainsLosses in macro trading were led by commoditiescurrencies in FTVboth HTV and equities in HTV.FTV.

Total net realized and unrealized gains (losses) on investments and net investment income (loss) - other, returned income of $0.6$25.8 million and $63.8$61.6 million for the three months ended MarchJune 31,30, 2026 and 2025, respectively. Income for the three months ended MarchJune 31,30, 2026 was driven by investment income on a larger portfolio of higher-yieldinghigher yielding assets, partially offset by negative mark-to-market returns. Income for the three months ended MarchJune 31,30, 2025 was primarily driven by both investment income and positive mark-to-market returns.

Gross premiums written increased by $72.9$75.3 million, or 19.7%,21.8%, from $370.0$344.8 million for the three months ended MarchJune 31,30, 2025 to $442.9$420.1 million for the three months ended MarchJune 31,30, 2026, primarily driven by growth in both new and existing business in casualty and specialty insurance classes.

Net premiums earned increased by $50.2$49.4 million, or 20.9%,19.5%, from $240.6$253.2 million for the three months ended MarchJune 31,30, 2025 to $290.8$302.6 million for the three months ended MarchJune 31,30, 2026. The increase was primarily driven by growth in our specialty insurancecasualty and reinsurance classes and casualtyspecialty insurance classes. Specialty insurance growth was primarily driven by accident & health, fine art & specie and marine & energy; specialty reinsurance growth was primarily driven by surety reinsurance and treaty reinsurance; and casualtyCasualty insurance growth was primarily driven by U.S. excess and surplus lines and professional lines.lines, and specialty insurance growth was primarily driven by accident & health.

Third party fee income decreased by $1.8$2.0 million, from $4.3$3.8 million for the three months ended MarchJune 31,30, 2025 to $2.5$1.8 million for the three months ended MarchJune 31,30, 2026. The decrease was primarily due to a decrease in syndicate management fees. Effective July 1, 2025, the management of the third party syndicate was novated from Hamilton Managing Agency to another Lloyd's managing agency.

Attritional loss ratio - current year for the three months ended MarchJune 31,30, 2026 was 54.9%51.1% compared to 52.1%51.9% for the three months ended MarchJune 31,30, 2025, ana increasedecrease of 2.80.8 percentage points. The increasedecrease was primarily driven by athe changeabsence of large losses in businessthe mix,current including more specialty insurance business.quarter.

Attritional loss ratio - prior year for the three months ended MarchJune 31,30, 2026 was ana unfavorablefavorable 3.6%,4.6% compared to a favorable 2.2%3.0% for the three months ended MarchJune 31,30, 2025, ana increasedecrease of 5.81.6 percentage points. The unfavorablefavorable attritional loss ratio - prior year for the three months ended MarchJune 31,30, 2026 was primarily driven by additionalfavorable loss informationdevelopment in relationspecialty, toproperty theand Baltimorecasualty Bridgeinsurance collapse.classes.

Catastrophe losses - current year and prior year were $Nil$33.6 million and $1.1 million for the three months ended MarchJune 31,30, 2026.2026 and 2025, respectively. Catastrophe losses for the three months ended MarchJune 31,30, 2026 were driven by the Middle East conflict ($33.6 million). Catastrophe losses for the three months ended June 30, 2025 were asdriven aby resultsevere ofconvective thestorms California($1.6 wildfires of $130.6 million,million), partially offset by favorable prior year development of $9.2$0.5 million.

The acquisition cost ratio for the three months ended MarchJune 31,30, 2026 was 22.6%,26.5%, compared to 20.9%25.9% for the three months ended MarchJune 31,30, 2025.2025, an increase of 0.6 percentage points. The increase was primarily driven by a change in business mix, including morean proportional business writtenincrease in ourspecialty casualty reinsurance classes,insurance, partially offset by ana increasedecrease in cededproperty commissionand income.casualty Theinsurance three months ended March 31, 2025 benefited from higher reinstatement premiums, which do not attract acquisition costs.classes.

Other underwriting expenses for the three months ended March 31, 2026 were $9.1 million, a decrease of $5.0 million, or 35.6%, compared to $14.1$40.8 million for the three months ended MarchJune 31,30, 2026, an increase of $1.3 million, or 3.2%, compared to $39.5 million for the three months ended June 30, 2025. The decreaseincrease was primarily driven by Bermuda substance-based tax credits, partially offset by an increase in personnel costs.

The other underwriting expense ratio for the three months ended MarchJune 31,30, 2026 and 2025 decreased from 5.3%14.1% to 1.7%,12.9%, driven by the Bermuda substance-based tax credits, certain performance based management fees recognized by Ada Capital Management Limited for services provided to Ada Re, Ltd and growth in the premium base.base, partially offset by an increase in the underlying costs and a decrease in third party fee income.