Hamilton Insurance Group, Ltd. HG Form 10-Q filing Q2 FY2026

Item 1. Financial Statements

Hamilton Insurance Group, Ltd.

Unaudited Condensed Consolidated Balance Sheets

See accompanying notes to the unaudited condensed consolidated financial statements.

Hamilton Insurance Group, Ltd.

Unaudited Condensed Consolidated Statements of Operations and Comprehensive Income (Loss)

See accompanying notes to the unaudited condensed consolidated financial statements.

Hamilton Insurance Group, Ltd.

Unaudited Condensed Consolidated Statements of Shareholders' Equity

See accompanying notes to the unaudited condensed consolidated financial statements.

Hamilton Insurance Group, Ltd.

Unaudited Condensed Consolidated Statements of Cash Flows

See accompanying notes to the unaudited condensed consolidated financial statements.

Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

1. Organization

Hamilton Insurance Group, Ltd. ("Hamilton Group", the "Group", the "Company", "we", "us" or "our"), the ultimate group holding company, was incorporated on September 4, 2013, under the laws of Bermuda. On November 14, 2023, the Company consummated an initial public offering ("IPO") of its Class B common shares, which are listed on the New York Stock Exchange ("NYSE").

Our Bermuda operations are led by Hamilton Re, Ltd. ("Hamilton Re"), a registered Class 4 insurer incorporated in Bermuda. Hamilton Re writes property, casualty and specialty insurance and reinsurance on a global basis.

Hamilton Re US is a tax partnership that was formed pursuant to an arrangement between Hamilton Re and its Bermuda-incorporated affiliate, Hamilton ILS Holdings Limited. The tax partnership is treated as a U.S. corporation for U.S. tax purposes and is registered with the U.S. Internal Revenue Service, such that underwriting and investment income derived from capital allocated to Hamilton Re US are subject to U.S. taxation.

Ada Capital Management Limited ("ACML"), a wholly owned insurance agent incorporated and regulated in Bermuda, is authorized to underwrite on behalf of Ada Re, Ltd. ("Ada Re").

Our London operations are comprised of Hamilton Managing Agency Limited ("HMA"), a Lloyd’s managing agency, which manages our wholly aligned Syndicate 4000. Syndicate 4000 operates in the Lloyd’s market and underwrites property, casualty and specialty insurance and reinsurance business on a subscription basis.

Our Dublin operations are comprised of Hamilton Insurance Designated Activity Company ("HIDAC"), a Dublin-based insurer with a U.K. branch and extensive licensing in the United States, including excess and surplus lines and reinsurance in all 50 states.

Hamilton Managing General Agency Americas LLC ("HMGA Americas") is licensed throughout the United States and underwrites on behalf of the Group's London, Dublin and Bermuda operations solely in respect of Hamilton Re US, providing access from the U.S. to the Lloyd's market, the Group's rated Irish carrier and the Group's Bermuda balance sheet, respectively.

Hamilton Select Insurance Inc. ("Hamilton Select") is a U.S. domestic excess and surplus lines carrier incorporated in Delaware and authorized to write excess and surplus business in all 50 states.

Two Sigma Hamilton Fund, LLC ("TS Hamilton Fund"), is a Delaware limited liability company. In 2013, Hamilton Re entered into a limited liability company agreement with TS Hamilton Fund and Two Sigma Principals, LLC (the "Managing Member"), a related party Delaware limited liability company which serves as the managing member of TS Hamilton Fund. The Managing Member, on behalf of TS Hamilton Fund, has engaged Two Sigma Investments, LP ("Two Sigma"), a related party Delaware limited partnership, to serve as the fund’s investment manager. Two Sigma is an investment adviser registered with the U.S. Securities and Exchange Commission, specializing in quantitative analysis.

On April 1, 2026, the Company, Hamilton Re, TS Hamilton Fund, the Managing Member and Two Sigma entered into an investment agreement (the "Original Investment Agreement") relating to Hamilton Re’s investment in TS Hamilton Fund. The Original Investment Agreement replaced and superseded the commitment agreement, dated July 1, 2023, as amended on January 1, 2025 (the "Prior Commitment Agreement"), which previously governed such investment. On June 1, 2026, the parties entered into an amended and restated investment agreement (the “Investment Agreement”), which amended and restated, and superseded in its entirety, the Original Investment Agreement. The principal effect of the June 1, 2026 amendment and restatement was to relocate the provisions governing withdrawals from the Investment Agreement to the Sixth Amended and Restated Limited Liability Company Agreement of the TS Hamilton Fund dated May 21, 2026 (the “LLCA”). The terms governing withdrawals were not substantively changed in connection with such amendment and restatement, and, other than the relocation of such provisions, no other material terms were modified.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

Unconsolidated Related Parties

Ada Re is a special purpose insurer funded by investors and formed to provide fully collateralized reinsurance and retrocession to both Hamilton Group and third party cedants.

Easton Re has issued an industry loss index-triggered catastrophe bond that provides the Company's operating platforms with multi-year risk transfer capacity to protect against named storm risk in the United States and earthquake risk in the United States and Canada. See Note 6, Reinsurance for further details.

2. Summary of Significant Accounting Policies

There have been no material changes to the Company's significant accounting policies as described in its Annual Report on Form 10-K for the year ended December 31, 2025 (the "Form 10-K"), except as described below.

a.Basis of Presentation

These unaudited condensed consolidated financial statements have been prepared in accordance with accounting principles generally accepted in the United States ("GAAP") and Article 10 of Regulation S-X, for interim financial information. Accordingly, they do not include all of the information and footnotes required by GAAP for complete financial statements. In addition, the year-end balance sheet data was derived from audited financial statements but does not include all disclosures required by GAAP. In the opinion of management, these unaudited condensed consolidated financial statements reflect all adjustments (consisting of normal recurring accruals) considered necessary for a fair presentation of the Company's financial position and results of operations as at the end of, and for, the periods presented.

These financial statements include the accounts of Hamilton Group, Hamilton Re, Hamilton U.K. Holdings Limited, Hamilton Select, HMGA Americas, ACML, and TS Hamilton Fund. All significant intercompany transactions and balances have been eliminated on consolidation. Certain comparative information has been reclassified to conform to the current year presentation.

b.Use of Estimates

The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported and disclosed amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. Actual results could differ from those estimates. The major estimates recorded in the Company’s financial statements include, but are not limited to, the reserve for losses and loss adjustment expenses, premiums written and earned, ceded reinsurance, unpaid losses and loss adjustment expenses recoverable and the fair value of investments.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

3. Investments

Fixed Maturity and Short-Term Investments - Trading

The Company’s fixed maturity and short-term investments are as follows:

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

Contractual Maturities Summary

The following table presents contractual maturities of fixed maturity securities. Expected maturities will differ from contractual maturities because borrowers may have the right to call or prepay obligations with or without call or prepayment penalties.

Investments in Two Sigma Funds

TS Hamilton Fund invests in Two Sigma Funds ("Two Sigma Funds"), which are stated at their estimated fair values, which generally represent the Company’s proportionate interest in the members’ equity of the Two Sigma Funds as reported by the respective funds based on the net asset value ("NAV") provided by the fund administrator. The Company accounts for its investment in Two Sigma Funds under the variable interest model at NAV as a practical expedient for fair value in the consolidated balance sheet.

The Company owns the following interest in each of the Two Sigma Funds:

The Company, through its investments in the Two Sigma Funds, seeks to achieve absolute dollar-denominated returns on a substantial capital base, primarily by combining multiple hedged and leveraged systematic and non-systematic investment strategies with proprietary risk management and execution techniques. These strategies include, but are not limited to, technical and statistically-based, fundamental-based, event-based, market condition-based and spread-based strategies as well as contributor-based and/or sentiment-based strategies and blended strategies.

• STV primarily utilizes systematic strategies to trade exchange-traded funds.
• ESTV primarily utilizes systematic strategies to trade U.S. listed and non-U.S.-listed equity securities, swap contracts, money market funds, government debt securities, futures and foreign currency forward contracts.
• ATV primarily utilizes systematic strategies to trade a diversified, global, equity market neutral portfolio, predominantly of equity securities, equity-related derivatives and other related instruments.
• FTV primarily utilizes systematic macro strategies to trade exchange traded funds, exchange memberships, government debt securities, money market funds, option contracts, swap contracts, futures and forward contracts.
• HTV primarily utilizes systematic strategies and non-systematic discretionary strategies to trade futures, futures options, foreign currency spot, forward and option contracts, exchange-traded products ("ETPs") and ETP options, debt securities, and various types of derivatives and other instruments.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

• NTV primarily utilizes non-systematic discretionary macro strategies that combine human discretion with quantitative analysis for purposes of trading globally across various asset classes.
• KTV primarily utilizes non-systematic discretionary strategies that combine human discretion with quantitative analysis to trade futures, futures options, foreign currency spot, forward and option contracts, ETPs and ETP options, debt securities, and various types of derivatives and other instruments.

The Company’s investments in Two Sigma Funds are as follows:

The following table summarizes certain investments of the Two Sigma Funds where TS Hamilton Fund’s proportionate share of the fair value of the investment represents more than 5% of TS Hamilton Fund’s members’ equity:

(1) Values represent TS Hamilton Fund’s proportionate share of the aggregate of the Two Sigma Funds' total holdings.

Two Sigma and the Managing Member are related parties to the Company as described further in Note 1, Organization. The LLCA requires TS Hamilton Fund to incur a management fee of 2.5% per annum of the non-managing members' equity in the net asset value of the TS Hamilton Fund. The management fee for the three months ended June 30, 2026 and 2025 was $14.9 million and $13.1 million, respectively, and the management fee for the six months ended June 30, 2026 and 2025 was $28.6 million and $25.5 million, respectively.

Under the terms of the LLCA, the Managing Member is entitled to an incentive allocation equal to 30% of TS Hamilton Fund’s net profits, subject to high watermark provisions, and adjusted for withdrawals and any incentive allocation to the Managing Member. In the event there is a net loss during a quarter and a net profit during any subsequent quarter, the Managing Member is entitled to a modified incentive allocation whereby the regular incentive allocation will be reduced by 50% until subsequent cumulative net profits are credited in an amount equal to 200% of the previously allocated net losses. The Managing Member is also entitled to receive an additional incentive allocation as of the end of each fiscal year (or on any date Hamilton Re withdraws all or a portion of its capital), in an amount equal to 25% of the Excess Profits. "Excess Profits" for any given fiscal year (or other such accounting period) means the net profits over 10% for such fiscal year, net of management fees and expenses and gross of incentive allocations, but only after recouping previously unrecouped net losses. To the extent Hamilton Re contributes capital other than at the beginning of a fiscal year or withdraws capital other than at the end of a fiscal year, the additional incentive allocation hurdle with respect to such capital is prorated. The aggregate incentive allocation (inclusive of the additional incentive allocation) for the three months ended June 30, 2026 and 2025 was $111.0 million and $80.4 million, respectively, and the aggregate incentive allocation (inclusive of the additional incentive allocation) for the six months ended June 30, 2026 and 2025 was $194.5 million and $180.7 million, respectively.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

On April 1, 2026, the Company, Hamilton Re, TS Hamilton Fund, the Managing Member and Two Sigma entered into the Original Investment Agreement relating to Hamilton Re’s investment in the TS Hamilton Fund. The Original Investment Agreement replaced and superseded the Prior Commitment Agreement, which previously governed such investment. On June 1, 2026, the parties entered into the amended and restated Investment Agreement, which amended and restated, and superseded in its entirety, the Original Investment Agreement. The principal effect of the June 1, 2026 amendment and restatement was to relocate the provisions governing withdrawals from the Investment Agreement to the LLCA. The terms governing withdrawals were not substantively changed in connection with such amendment and restatement, and, other than the relocation of such provisions, no other material terms were modified.

Under the Investment Agreement, Hamilton Re has agreed to use its reasonable best efforts to maintain an investment in the TS Hamilton Fund in an amount not less than the lesser of (i) $1.8 billion or (ii) 60% of Hamilton Group’s net tangible assets (the "Minimum Commitment Amount"). The Investment Agreement distinguishes between capital attributable to amounts in excess of the Minimum Commitment Amount ("Sub‑Series A Interests") and capital at or below such amount ("Sub‑Series B Interests"). The terms governing withdrawals, as set forth in the LLCA, provide that (i) withdrawals of Sub‑Series A Interests may be made as of the last calendar day of each calendar quarter upon at least 55 days’ prior notice, and (ii) withdrawals of Sub‑Series B Interests may be made monthly, subject to a six‑month notice requirement and monthly withdrawal limitations, including a maximum withdrawal of one-twelfth of the Sub‑Series B Interests per month.

Total Net Realized and Unrealized Gains (Losses) on Investments and Net Investment Income (Loss)

The components of total net realized and unrealized gains (losses) on investments and net investment income (loss) are as follows:

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

Net Realized Gains (Losses) on Investments

The components of net realized gains (losses) on investments are as follows:

Net Unrealized Gains (Losses) on Investments

The components of net unrealized gains (losses) on investments are as follows:

Pledged Assets

At June 30, 2026 and December 31, 2025, pledged investments at fair value were comprised of $289.9 million and $263.1 million, respectively, securing a portion of the capital requirements for business written at Lloyd's, $294.6 million and $265.0 million, respectively, held in trust accounts for the benefit of U.S. state regulatory authorities and $90.0 million and $90.4 million, respectively, securing other underwriting obligations. In addition, certain investments were pledged as security for letter of credit facilities as described further in Note 9, Debt and Credit Facilities.

At June 30, 2026 and December 31, 2025, restricted cash and cash equivalents balances were comprised of $107.2 million and $106.2 million, respectively, securing other underwriting obligations, $2.5 million and $1.4 million, respectively, securing a portion of the capital requirements for business written at Lloyd's and $1.9 million and $2.1 million, respectively, in trust accounts for the benefit of regulatory authorities.

Total cash and cash equivalents and restricted cash and cash equivalents of $829.0 million presented in the statement of cash flows was comprised of cash and cash equivalents of $717.3 million and restricted cash and cash equivalents of $111.6 million on the balance sheet at June 30, 2026. Total cash and cash equivalents and restricted cash and cash equivalents of $1.2 billion presented in the statement of cash flows at December 31, 2025 was comprised of cash and cash equivalents of $1.1 billion and restricted cash and cash equivalents of $109.7 million on the balance sheet.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

4. Fair Value

Financial Instruments Subject to Fair Value Measurements

Accounting guidance over fair value measurements requires that a fair value measurement reflect the assumptions market participants would use in pricing an asset or liability based on the best information available. Assumptions include the risks inherent in a particular valuation technique (such as a pricing model) and/or the risks inherent in the inputs to the model. The fair value of a financial instrument is the amount that would be received to sell an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date (the "exit price"). Instruments that the Company owns are marked to bid prices.

Basis of Fair Value Measurements

Fair value measurement accounting guidance also establishes a fair value hierarchy that prioritizes the inputs to the respective valuation techniques used to measure fair value. The hierarchy gives the highest priority to unadjusted quoted prices in active markets for identical assets or liabilities (Level 1 measurements) and the lowest priority to unobservable inputs (Level 3 measurements). An asset or liability’s classification within the fair value hierarchy is based on the lowest level of significant input to its valuation. The three levels of the fair value hierarchy are:

• Level 1 - Inputs that reflect unadjusted quoted prices in active markets for identical assets or liabilities that the Company has the ability to access at the measurement date;
• Level 2 - Inputs other than quoted prices included within Level 1 that are observable for the asset or liability either directly or indirectly, including inputs in markets that are not considered to be active; and
• Level 3 - Inputs that are both significant to the fair value measurement and unobservable.

Assets Recorded at Fair Value - Fixed Maturity and Short-term Investments

The following section describes the valuation methodologies used to determine the fair value of the Company’s fixed maturity and short-term investments by asset class:

• U.S. government treasuries: fair value based on observable market inputs such as quoted prices, reported trades, quoted prices for similar issuances and benchmark yields;
• U.S. states, territories and municipalities: fair value based on observable market inputs such as quoted market prices, quoted prices for similar securities, benchmark yields and credit spreads;
• Non-U.S. sovereign governments and supranationals: fair value based on observable market inputs such as quoted market prices, quoted prices for similar securities and models with observable inputs such as benchmark yields and credit spreads, and then, where applicable, converted to U.S. Dollars using an exchange rate from a nationally recognized source;
• Corporate: fair value based on observable market inputs such as quoted market prices, quoted prices for similar securities, benchmark yields and credit spreads;
• Asset-backed and mortgage-backed securities: fair value based on observable inputs such as quoted prices, reported trades, quoted prices for similar issuances or benchmark yields and cash flow models using observable inputs such as prepayment speeds, collateral performance and default spreads; and
• Short-term investments: fair value based on observable market inputs such as quoted prices, reported trades, quoted prices for similar issuances and benchmark yields.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

The following table presents the financial instruments measured at fair value on a recurring basis:

The carrying values of cash and cash equivalents, restricted cash and cash equivalents, accrued investment income, receivables for investments sold, certain other assets, payables for investments purchased, and certain other liabilities approximate their fair values.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

5. Variable Interest Entities

TS Hamilton Fund

TS Hamilton Fund meets the definition of a variable interest entity ("VIE") principally because the Managing Member does not hold substantive equity at risk in the entity but controls all of the decision making authority over it. Therefore, the Company assessed its ownership in the VIE to determine if it is the primary beneficiary. The Managing Member is a related party to the Company and collectively they hold all of the variable interest. The Company performed an assessment of all relevant facts and circumstances and determined that it is the entity within the related party group for whom substantially all of the activities of the VIE are conducted. As a result, the Company concluded that it is the primary beneficiary of TS Hamilton Fund.

Activity in the non-controlling interest of TS Hamilton Fund was as follows:

The following table presents the total assets and total liabilities of TS Hamilton Fund. Creditors or beneficial interest holders of TS Hamilton Fund have no recourse to the general credit of the Company as the Company’s obligation is limited to the amount of its committed investment.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

6. Reinsurance

The Company purchases reinsurance and other protection to manage its risk portfolio and to reduce its exposure to large losses. The Company currently has in place contracts that provide for recovery of a portion of certain loss and loss adjustment expenses, generally in excess of various retentions or on a proportional basis. Amounts recoverable under reinsurance contracts are recorded as assets. The Company remains liable to the extent that any reinsurance company fails to meet its obligations.

Allowance for Expected Credit Losses

Premiums receivable, paid losses recoverable, and unpaid losses and loss adjustment expenses recoverable comprise the Company's most significant credit exposures not carried at fair value. The Company has not historically experienced significant credit losses. In determining an allowance for these assets, the Company considers historical information in combination with counterparty financial strength ratings and the extent to which balances are collateralized. The Company assesses the risk of future default by evaluating current market conditions for the likelihood of default and calculates its provision for current expected credit losses under the probability of default and loss given default methodology.

Premiums Receivable

Premiums receivable are estimated based on policy terms and reports received from the underlying counterparties, supplemented by management's judgment. Due to the nature of the (re)insurance business, the Company routinely receives reports and premiums subsequent to the inception of the coverage period. At June 30, 2026, the Company’s premiums receivable balance, net of credit provisions of $3.7 million, was $1.2 billion. At December 31, 2025, the Company’s premiums receivable balance, net of credit provisions of $3.4 million, was $939.8 million.

The following table provides a roll forward of the provision for current expected credit losses of the Company's premiums receivable:

Reinsurance Balances Recoverable

Reinsurance balances recoverable is comprised of amounts due from reinsurers based on the claim liabilities associated with the reinsured policy. The Company accrues amounts due from reinsurers based on estimated ultimate contract losses. At June 30, 2026, the Company’s paid and unpaid reinsurance recoverable balances net of credit provisions were $99.2 million and $1.5 billion, respectively, with a total corresponding provision for current expected credit losses of $1.4 million. At December 31, 2025, the Company’s paid and unpaid reinsurance recoverable balances net of credit provisions were $93.7 million and $1.4 billion, respectively, with a total corresponding provision for current expected credit losses of $1.7 million.

The following table provides a roll forward of the provision for current expected credit losses of the Company's reinsurance recoverable:

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

The distribution of the Company’s paid losses recoverable and unpaid losses and loss adjustment expenses recoverable as categorized by major rating agencies were as follows:

At June 30, 2026 and December 31, 2025, the three largest balances by reinsurer accounted for 21%, 16% and 12%, and 20%, 18% and 12%, respectively, of paid losses recoverable and unpaid losses and loss adjustment expenses recoverable.

Loss Portfolio Transfer

On February 6, 2020, the Company entered into a loss portfolio transfer agreement (the "LPT"), under which the insurance liabilities arising from certain casualty risks for the Lloyd's Years of Account ("YOA") 2016, 2017 and 2018 were retroceded to a third party in exchange for total premium of $72.1 million. This transaction was accounted for as retroactive reinsurance under which cumulative ceded losses exceeding the LPT premium are recognized as a deferred gain liability and amortized into income over the settlement period of the ceded reserves in proportion to cumulative losses collected over the estimated ultimate reinsurance recoverable. The amount of the deferred gain is recalculated each reporting period based on updated ultimate loss estimates. Consequently, cumulative adverse development subsequent to the signing of the LPT may result in significant losses from operations until periods when the recalculated deferred gain is recognized as a benefit to earnings.

At June 30, 2026 and December 31, 2025, the balance of reinsurance recoverable on unpaid losses due under this LPT was $23.5 million and $22.7 million, respectively. Amortization of the deferred gain was income of $2.4 million and an expense of $2.2 million during the three months ended June 30, 2026 and 2025, respectively, and income of $2.6 million and an expense of $2.7 million during the six months ended June 30, 2026 and 2025, respectively, which was recorded through losses and loss adjustment expenses in accordance with the actual loss payments and updated estimates of ultimate losses of the subject business.

Catastrophe Bond Reinsurance

In December 2023, Hamilton Group sponsored an industry loss index-triggered catastrophe bond through the issuance of Series 2024-1 Class A Principal-at-Risk Variable Rate Notes by Bermuda 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. The Company recorded reinsurance premiums ceded of $Nil for each of the three months ended June 30, 2026 and 2025. The Company recorded reinsurance premiums ceded of $15.9 million and $15.2 million for the six months ended June 30, 2026 and 2025, respectively.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

7. Reserve for Losses and Loss Adjustment Expenses

The following table presents a reconciliation of unpaid losses and loss adjustment expenses ("LAE"):

Net unfavorable prior year development of $17.3 million for the six months ended June 30, 2026 was driven by unfavorable prior year development of $13.1 million and $4.2 million on attritional and catastrophe losses, respectively. See below for further details:

• Net unfavorable development of $15.9 million on casualty contracts, primarily driven by unfavorable development in certain casualty classes and additional information on one large loss;
• Net unfavorable development of $14.5 million, driven by additional loss information in relation to the Baltimore Bridge collapse; partially offset by
• Net favorable development of $12.3 million on specialty contracts, primarily driven by a reduction in loss estimates on certain classes;
• Net favorable development of $0.6 million on property contracts; and
• In addition, casualty business protected by the LPT discussed in Note 6, Reinsurance, benefited from a change in the deferred gain of $2.6 million, partially offset by unfavorable development in the underlying reserves of $2.4 million, for a total net positive earnings impact of $0.2 million.

Net favorable prior year development of $34.7 million for the six months ended June 30, 2025 was primarily driven by $17.6 million and $17.1 million of favorable prior year development on catastrophe and attritional losses, respectively. See below for further details:

• Net favorable development of $35.6 million on property contracts, primarily driven by favorable prior year development on Hurricane Ian, the June 2023 severe convective storms and Hurricane Idalia, in addition to favorable attritional loss development;
• Net favorable development of $18.3 million on specialty contracts, primarily driven by a reduction in loss estimates on certain classes; partially offset by

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

• Net unfavorable development of $20.4 million on casualty contracts, primarily driven by unfavorable prior year development on discontinued lines of business and additional information on certain large losses; and
• In addition, casualty business protected by the LPT discussed in Note 6, Reinsurance, benefited from favorable development in the underlying reserves of $3.9 million, which was partially offset by a change in the deferred gain of $2.7 million, for a total net positive earnings impact of $1.2 million.

Reinsurance recoverable on unpaid losses related to the LPT discussed in Note 6, Reinsurance was recognized for each of the six months ended June 30, 2026 and 2025 in the reconciliation of beginning and ending gross and net loss and LAE reserves.

Acquisition Costs

The Company amortized acquisition costs of $145.4 million and $122.8 million for the three months ended June 30, 2026 and 2025, respectively, and $289.9 million and $239.7 million for the six months ended June 30, 2026 and 2025, respectively.

Middle East Conflict

The net reserves for losses and loss adjustment expenses related to the Middle East conflict are subject to significant uncertainty. As at June 30, 2026 and December 31, 2025, net recorded reserves relating to the Middle East conflict totaled $45.5 million and $Nil, respectively.

California Wildfires

The net reserves for losses and loss adjustment expenses related to the California wildfires are also subject to significant uncertainty. As at June 30, 2026 and December 31, 2025, net recorded reserves relating to the California wildfires totaled $45.9 million and $57.5 million, respectively.

Baltimore Bridge

The net reserves for losses and loss adjustment expenses related to the Francis Scott Key Baltimore Bridge collapse on March 26, 2024 are also subject to significant uncertainty. As at June 30, 2026 and December 31, 2025, net recorded reserves totaled $11.4 million and $20.5 million, respectively.

Ukraine Conflict

The net reserves for losses and loss adjustment expenses related to the ongoing Ukraine conflict are also subject to significant uncertainty. As at June 30, 2026 and December 31, 2025, net recorded reserves totaled $8.0 million and $59.5 million, respectively.

While the Company believes, based on current facts and circumstances, that its estimates of net reserves for losses and loss adjustment expenses are adequate for losses and loss adjustment expenses that have been incurred at June 30, 2026, the Company will continue to monitor its assumptions as new information becomes available and will adjust its estimate of net reserves for losses and loss adjustment expenses as appropriate. Actual ultimate losses for these events may differ materially from the Company's current estimates.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

8. Segment Reporting

The Company has determined its reportable business segments based on the information used by management in assessing performance and allocating resources to underwriting operations and has identified two reportable business segments - International and Bermuda. Each of the Company's identified reportable segments has a Chief Executive Officer who is responsible for the overall profitability of their segment and who regularly reports and is directly accountable to the chief operating decision maker ("CODM"): the Chief Executive Officer of the consolidated group. The CODM's responsibilities include providing leadership to all levels of employees; developing culture, values, and ethos; setting the Company's strategy, vision and direction; and overall responsibility for the success and profitability of the Company, including evaluating segment performance.

The CODM evaluates reportable segment performance based on the segments' 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 the Company does not manage its assets by reportable segment, investment income and assets are not allocated to reportable segments.

The Company's core business is underwriting and its underwriting results are reflected in its reportable segments: (1) International, which is comprised of property, casualty and specialty insurance and reinsurance classes of business originating from the Company’s London, Dublin, and Hamilton Select operations; and (2) Bermuda, which is comprised of property, casualty and specialty insurance and reinsurance classes of business originating from Hamilton Re, Bermuda and Hamilton Re US and subsidiaries. The Company considers many factors, including the nature of each segment’s products, client types, production sources, distribution methods and the regulatory environment, in determining the aggregated operating segments.

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

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

The following table presents gross premiums written by the geographical location of the Company's subsidiaries:

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

9. Debt and Credit Facilities

Debt

On June 10, 2025, Hamilton Group entered into a $150 million term loan credit arrangement (the "Facility") with various lenders as arranged by Wells Fargo Securities, LLC. The Facility replaces Hamilton Group's $150 million term loan credit agreement, as amended through and including June 23, 2022, between Hamilton Group and the lenders thereto (as amended the "Existing Loan Agreement"). The Facility will be used to refinance the indebtedness outstanding under the Existing Loan Agreement. All or a portion of the loan issued under the Facility bears interest, at the option of Hamilton Group, at either (a) a base rate plus an applicable margin or (b) the Adjusted Term Secured Overnight Financing Rate ("SOFR") plus an applicable margin, in each case with the applicable margin determined with reference to the Company's long-term issuer default rating as assigned by Fitch. The Facility matures on June 9, 2028, unless accelerated pursuant to the terms of the Facility, and it contains usual and customary representations, warranties, conditions and covenants for bank loan facilities of this type. The Facility also includes financial covenants, including a financial strength rating test, a minimum consolidated tangible net worth test and a maximum consolidated indebtedness to total capitalization ratio. As at June 30, 2026, the Company was in compliance with all covenants.

The following table presents the gross outstanding loan balance, loan fair value and unamortized loan issuance costs:

Debt issuance costs are amortized over the period during which the Facility is outstanding, as an offset to net investment income (loss). The Company amortized debt issuance costs of $0.1 million or less in each of the three and six months ended June 30, 2026 and 2025. The Company’s debt is classified as Level 3 within the fair value hierarchy because it is valued using an income approach, which utilizes a discounted cash flow technique that considers the credit profile of the Company.

Credit Facilities

The Company has several available letter of credit ("LOC") facilities and a revolving loan facility provided by commercial banks. The LOC facilities are utilized to provide collateral to reinsureds of Hamilton Re and its affiliates to the extent required under insurance and reinsurance agreements and to support capital requirements at Lloyd’s.

On December 5, 2018 and December 27, 2018, Hamilton Re entered into a Master Agreement for Issuance of Payment Instruments and a Facility Letter for Issuance of Payment Instruments with CitiBank Europe Plc ("CitiBank Europe"), under which CitiBank Europe agreed to provide an uncommitted secured letter of credit facility for the issuance of standby letters of credit or similar instruments in multiple currencies. On November 15, 2024, letter of credit capacity under this facility was increased to $250 million. At all times during which it is a party to the facility, Hamilton Re is obligated to pledge to CitiBank Europe cash and/or securities with a value that equals or exceeds the aggregate face amount of its then-outstanding letters of credit. The Master Agreement contains events of default customary for facilities of this type. In the facility letter, Hamilton Re makes representations and warranties that are customary for facilities of this type and agrees that it will comply with certain informational and other undertakings.

On June 10, 2025, Hamilton Group and Hamilton Re entered into a $450 million credit agreement with a syndication of lenders (the "Unsecured Facility"). Under the Unsecured Facility, the lenders have agreed to provide up to an aggregate of $450 million of letter of credit capacity for Hamilton Re, up to $150 million of which may be utilized for revolving loans to be issued to Hamilton Group. At June 30, 2026, there were no loan amounts outstanding under the Unsecured Facility. Letters of credit issued under the Unsecured Facility bear interest at a rate determined by Hamilton Group’s long-term issuer default rating, while revolving loans, if drawn, accrue interest at the option of Hamilton Group at either (a) a base rate plus an applicable margin or (b) Adjusted Term SOFR plus an applicable margin. In each case, the applicable margin is determined based on Hamilton Group’s long-term issuer default rating as assigned by Fitch. Currently, any letters of credit issued under the facility bear interest at a rate of 125 basis points. Revolving loans, if issued, are subject to a fee equal to the prime rate plus 50 basis points or Adjusted Term SOFR plus a margin of 150 basis points. To the extent such loans are issued, the available letter of

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

credit capacity shall decrease proportionally, such that the aggregate credit exposure for the lenders under the Unsecured Facility is $450 million. Amounts unutilized under the Unsecured Facility are subject to a fee based upon Hamilton Group's long-term issuer default rating as assigned by Fitch, currently equal to 17.5 basis points. The Unsecured Facility is subject to representations and warranties, affirmative and negative covenants and events of default that the Company considers customary for similar facilities. The Unsecured Facility also includes financial covenants, including a financial strength rating test, a minimum consolidated tangible net worth test and a maximum consolidated indebtedness to total capitalization ratio. Capacity is provided by Wells Fargo, National Association, Truist Bank, Commerzbank AG, New York Branch, Citizens Bank, N.A., HSBC Bank USA, National Association, and Barclays Bank PLC. Unless renewed or otherwise terminated in accordance with its terms, the Unsecured Facility has a maturity date of June 9, 2028.

On October 23, 2025, Hamilton Re amended its letter of credit facility agreement with UBS AG ("UBS") under which UBS and certain of its affiliates agreed to make available to Hamilton Re a secured letter of credit facility in an amount that is equal to the greater of (i) $25 million and (ii) the LOC amount issued and outstanding, provided that the amount shall not at any time be greater than $75 million, for a term that will expire on October 23, 2026. The facility bears a fee of 140 basis points on the total available capacity.

In addition, on October 20, 2025, Hamilton Re amended the unsecured letter of credit facility agreement that it utilizes to provide Funds at Lloyd's ("FAL") ("FAL LOC Facility") to support the FAL requirements of Syndicate 4000. Capacity is provided by ING Bank N.V., London Branch, Commerzbank AG, New York Branch, and Deutsche Bank AG, London Branch. The FAL LOC Facility was renewed in the amount of $260 million for a term that expires on December 31, 2029. The facility bears a fee of 150 basis points on the borrowed amount.

The Company’s obligations under its credit facilities require Hamilton Group, Hamilton Re and the other parties thereto to comply with various financial and reporting covenants. All applicable entities were in compliance with all such covenants at June 30, 2026.

Certain of the Company's credit facilities are secured by pledged interests in the TS Hamilton Fund, the Company's fixed income security portfolio, or cash. The Company’s credit facilities and associated securities pledged, were as follows:

(1) Cash pledged as security under letter of credit and revolving loan facilities is included in restricted cash securing other underwriting obligations under Pledged Assets in Note 3, Investments.

The Company has recognized interest expense related to its debt and credit facilities of $4.8 million and $4.7 million for the three months ended June 30, 2026 and 2025, respectively, and $9.5 million and $10.3 million for the six months ended June 30, 2026 and 2025, respectively.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

10. Share Capital

Authorized and Issued

Hamilton Group’s share capital is comprised as follows:

The following is a summary of the activity related to common shares authorized:

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

The following is a summary of the activity related to common shares issued and outstanding:

Share Repurchases

On November 4, 2025, the Board of Directors authorized the repurchase of the Company's common shares in the aggregate amount of $150.0 million, in addition to remaining amounts under the prior authorization (collectively, the "Authorization"), under which the Company may repurchase shares through open market repurchases and/or privately negotiated transactions. The Authorization will expire when the Company has repurchased the full value of shares authorized, unless terminated earlier by the Board of Directors. All shares repurchased under the Authorization were subsequently cancelled. As of June 30, 2026, $136.7 million remained available for repurchase under the Authorization.

Dividends

On February 18, 2026, the Board of Directors declared a special dividend of $2.00 per share, or $205.7 million. The dividend was paid on March 30, 2026, to common shareholders of record as of March 6, 2026.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

Share Classes

In general, holders of Class A common shares and Class B common shares have one vote for each common share held while the Class C common shares have no voting rights, except as required by law. However, each holder of Class A common shares and Class B common shares is limited to voting (directly, indirectly or constructively, as determined for U.S. federal income tax purposes) that number of common shares equal to 9.5% of the total combined voting power of all classes of shares of the Company (or, in the case of a class vote by the holders of the Class B common shares, such as in respect of the election or removal of directors other than for directors who are appointed by certain shareholders pursuant to the Shareholders Agreement and the Bye-laws, an amount calculated by multiplying (a) 9.5% and (b) the quotient of dividing (x) the total number of directors by (y) the number of directors elected by holders of Class B common shares). In addition, the Board of Directors may, in its absolute discretion, limit a shareholder’s voting rights when it deems it appropriate to do so to avoid certain material adverse tax, legal or regulatory consequences to the Company, any subsidiary of the Company, or any direct or indirect shareholder or its affiliates.

The Company Bye-laws provide for the automatic redesignation of shares upon any transfer, whether or not for value, from (i) Class A common shares to Class B common shares and from (ii) Class C common shares to Class B common shares. Upon notice from a Class A Member to the Company that certain Class B common shares are held by a Class A Member or a Permitted Transferee thereof, if so requested by the Class A Member and upon approval by a Simple Majority of the Board, such Class B common shares shall convert automatically into the same number of Class A common shares. The number of authorized and issued Class B common shares shall be reduced by the aggregate number of such issued Class B common shares so converted and the number of authorized and issued Class A common shares shall be correspondingly increased by the same amount. Upon notice from a Class A Member and/or Class B Member to the Company and upon approval by a Simple Majority of the Board, such consent not to be unreasonably withheld or unduly delayed, such Class A common shares and/or Class B common shares shall be redesignated as Class C common shares. In such instance, the authorized and issued number of Class A common shares and/or Class B common shares shall be reduced by the aggregate number of such shares so converted and the number of Class C common shares shall be correspondingly increased by the same amount. Upon notice from a Class C Member to the Company and upon approval of a Simple Majority of the Board, such consent not to be unreasonably withheld or unduly delayed, such Class C common shares shall be redesignated Class B common shares. In such instance, the authorized and issued number of Class C common shares shall be reduced by the aggregate number of such Class C common shares so converted and the number of authorized and issued Class B common shares shall be correspondingly increased by the same amount.

During the three months ended June 30, 2026 and 2025, Nil and 1.9 million, respectively, Class C common shares were converted into Class B common shares at the request of the respective Class C Members and as approved by the Board.

During the six months ended June 30, 2026 and 2025, Nil and 3.4 million, respectively, Class C common shares were converted into Class B common shares at the request of the respective Class C Members and as approved by the Board.

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Hamilton Insurance Group, Ltd.

Notes to the Unaudited Condensed Consolidated Financial Statements

11. Earnings Per Share

The following table sets forth the computation of basic and diluted income (loss) per common share:

For each of the three months ended June 30, 2026 and 2025, Nil common shares available for issuance under share based compensation plans were excluded from the calculation of diluted income (loss) per share because the assumed exercise or issuance of such shares would be anti-dilutive.

For each of the six months ended June 30, 2026 and 2025, Nil common shares available for issuance under share-based compensation plans were excluded from the calculation of diluted income (loss) per share because the assumed exercise or issuance of such shares would be anti-dilutive.

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Item 2. Management's Discussion and Analysis of Financial Condition and Results of Operations

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 the Company's most recently filed Annual Report on Form 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.

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Index To Management's Discussion and Analysis of Financial Condition and Results of Operations

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Overview

Hamilton Insurance Group, Ltd. ("Hamilton," "Hamilton Group," the "Group," the "Company," "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 Investments, LP ("Two Sigma"). We operate globally, with underwriting operations in London, Dublin, Bermuda and across the United States.

We operate three principal underwriting platforms (Hamilton Global Specialty, Hamilton Select and Hamilton Re) that are categorized into two reporting business segments (International and Bermuda):

• International: International consists of business written out of our Lloyd’s syndicate and subsidiaries based in the United Kingdom, Ireland, and the United States, and includes the Hamilton Global Specialty and Hamilton Select platforms.
• 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 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.
• Hamilton Select, our U.S. domestic E&S carrier, writes casualty and property insurance for small-to-medium enterprise and lower middle market sized clients in 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.
• Bermuda: Bermuda consists of the Hamilton Re platform, made up of Hamilton Re and Hamilton Re US. Hamilton Re writes property, casualty and specialty reinsurance business on a global basis and also offers high excess Bermuda market specialty insurance products, predominantly for large U.S. commercial risks. Hamilton Re US writes casualty and specialty reinsurance business on a global basis.

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 flexibility, and real-time technology prowess, we can respond dynamically to capture opportunities as markets evolve.

One of our key strategic priorities is sustainable underwriting profitability across our portfolio. Our data-driven and disciplined underwriting processes position us to intelligently price and structure products and risks across our 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 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. While growth in the E&S market is 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 all market 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.

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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 trading environment in several 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 all 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. 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.

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 one managed by Two Sigma with exposures to certain Two Sigma equity and macro 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 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.

Two Sigma has broad discretion to allocate invested assets to different opportunities. Its current 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 Horizon Portfolio, LLC ("HTV"), Two Sigma Navigator Portfolio, LLC ("NTV") and Two Sigma Kuiper Portfolio, LLC ("KTV"). 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.

Effects of Inflation

Historically, inflation has not had a material effect on the Company’s consolidated results of operations. However, over the last several years, global economic inflation has increased, and there is a risk that it will remain elevated for an extended period. Inflation is subject to many macroeconomic factors beyond our control, including global banking policy, armed conflicts, geo-political risks and supply chain issues. An inflationary economy may result in higher losses and loss adjustment expenses, negatively impact the performance of our fixed income security investment portfolio, or increase our operating expenses, among other unfavorable effects. The ultimate effects of an inflationary or deflationary period are subject to high uncertainty and cannot be accurately estimated until the actual costs are known.

In the wake of a catastrophe loss there is a risk of specific inflationary pressures in the local economy, which is considered in our catastrophe loss models. Similarly, the Company incorporates the anticipated effects of inflation in our ultimate estimate of the reserves for unpaid losses and loss adjustment expenses on certain long-tail lines of business. As with general economic inflation, the actual effects of inflation on reserves for losses and loss adjustment expenses and results of operations cannot be accurately known until all of the underlying claims are ultimately settled.

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Taxes

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 June 30, 2026, 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 Two initiative. Specifically, it provided that for purposes of calculating the UTPR, a deduction for the ETA will not be allowed in years after 2026. Accordingly, when Hamilton Group becomes subject to the 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 UTPR top-up tax on its Bermuda earnings, the liability would be recorded in the period and jurisdiction in which it is incurred.

Summary of Critical Accounting Estimates

Our critical accounting estimates include "Reserve for Losses and Loss Adjustment Expenses", "Premiums Written and Earned", "Ceded Reinsurance and Unpaid Losses and Loss Adjustment Expenses Recoverable" and "Fair Value of Investments" and are discussed in Management’s Discussion and Analysis of Financial Condition and Results of Operations in the Group’s Form 10-K for the year ended December 31, 2025. There have been no material changes to our critical accounting estimates as disclosed in the Form 10-K for the year ended December 31, 2025.

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Consolidated Results of Operations

The following is a comparison of selected data for our consolidated results of operations:

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The following table summarizes book value per share and balance sheet data:

(1) Third party fee income 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.

(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 $13.0 million and $12.9 million for the three months ended June 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.

(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.

(4) Net investment income (loss) is presented net of investment management fees.

(5) Refer to 'Management’s Discussion and Analysis of Financial Condition and Results of Operations—Consolidated Results of Operations—Corporate and Other' for further details.

Operating Highlights

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

Gross premiums written Gross premiums written were $831.0 million and $712.0 million for the three months ended June 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 and insurance classes, primarily as a result of rate decreases for the current quarter.

Underwriting results The combined ratio was 95.0% and 86.8% for the three months ended June 30, 2026 and 2025, respectively. The increase was primarily driven by an increase in the catastrophe loss ratio and acquisition cost ratio, partially offset by a decrease in the other underwriting expense ratio.

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Losses and Loss Adjustment Expenses

Attritional loss ratio - current year for the three months ended June 30, 2026 was 53.3% compared to 53.0% for the three months ended June 30, 2025, an increase of 0.3 percentage points. The increase was primarily driven by a change in business mix, including more casualty reinsurance business.

Attritional loss ratio - prior year for the three months ended June 30, 2026 was a favorable 0.1% compared to a favorable 0.5% for the three months ended June 30, 2025, an increase of 0.4 percentage points. The attritional loss ratio - prior year for the three months ended June 30, 2026 was primarily driven by favorable development in both our International and Bermuda property classes and our International specialty and casualty classes, partially offset by unfavorable development in certain Bermuda casualty classes. The attritional loss ratio - prior year for the three months ended June 30, 2025 was primarily driven by favorable development in both our Bermuda and International property and specialty classes, partially offset by unfavorable development in certain Bermuda casualty classes.

Catastrophe losses - current year and prior year development were $49.9 million and $1.5 million for the three months ended June 30, 2026 and 2025, respectively. Catastrophe losses for the three months ended June 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 driven by severe convective storms ($9.9 million), partially offset by favorable prior year development of $8.4 million.

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Total Net Realized and Unrealized Gains (Losses) on Investments and Net Investment Income (Loss)

The components of total net realized and unrealized gains (losses) on investments and net investment income (loss) are as follows:

(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 $226.5 million and $167.5 million for the three months ended June 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 $115.5 million and $87.1 million for the three months ended June 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 5.1% and 4.4% for the three months ended June 30, 2026 and 2025, respectively.

For the three months ended June 30, 2026, TS Hamilton Fund experienced gains from single name equities trading within the equity market neutral vehicles STV, ESTV and ATV. Gains from single name equities trading were led by the U.S., followed by China onshore and 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 relative value rates vehicle, KTV. Gains from macro trading were led by equities in FTV and were partially offset by losses from macro trading within the scientific discretionary macro vehicle, NTV.

For the three months ended June 30, 2025, TS Hamilton Fund experienced gains from single name equities trading within the equity market neutral vehicles STV, ESTV and ATV. Gains from single name equities trading were led by the U.S., followed by Europe. Gains in TS Hamilton Fund were partially offset 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. Losses in macro trading were led by currencies in both HTV and FTV.

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

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Segment Information

We have determined our reportable business segments based on the information used by management in assessing performance and allocating resources to underwriting operations. We have identified two reportable business segments - International and Bermuda. Each of our identified reportable segments has a Chief Executive Officer who is responsible for the overall profitability of their segment and who regularly reports and is directly accountable to the chief operating decision maker ("CODM"): the Chief Executive Officer of the consolidated group. The CODM's responsibilities include providing leadership to all levels of employees; developing culture, values, and ethos; setting the Company's strategy, vision and direction; and overall responsibility for the success and profitability of the Company, including evaluating segment performance.

The CODM evaluates reportable segment performance based on the segments' 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.

Our core business is underwriting and our underwriting results are reflected in our reportable segments: (1) International, which is comprised of property, casualty and specialty insurance and reinsurance classes of business originating from the Company’s London, Dublin, and Hamilton Select operations; and (2) Bermuda, which is comprised of property, casualty and specialty insurance and reinsurance classes of business originating from Hamilton Re, Bermuda and Hamilton Re US and subsidiaries. We consider many factors, including the nature of each segment’s products, client types, production sources, distribution methods and the regulatory environment, in determining the aggregated operating segments.

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

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International Segment

Gross Premiums Written

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

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Net Premiums Earned

Net premiums earned increased by $49.4 million, or 19.5%, from $253.2 million for the three months ended June 30, 2025 to $302.6 million for the three months ended June 30, 2026. The increase was primarily driven by growth in our casualty and specialty insurance classes. Casualty insurance growth was primarily driven by U.S. excess and surplus lines and professional lines, and specialty insurance growth was primarily driven by accident & health.

Third Party Fee Income

Third party fee income decreased by $2.0 million, from $3.8 million for the three months ended June 30, 2025 to $1.8 million for the three months ended June 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.

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Losses and Loss Adjustment Expenses

Attritional loss ratio - current year for the three months ended June 30, 2026 was 51.1% compared to 51.9% for the three months ended June 30, 2025, a decrease of 0.8 percentage points. The decrease was primarily driven by the absence of large losses in the current quarter.

Attritional loss ratio - prior year for the three months ended June 30, 2026 was a favorable 4.6% compared to a favorable 3.0% for the three months ended June 30, 2025, a decrease of 1.6 percentage points. The favorable attritional loss ratio - prior year for the three months ended June 30, 2026 was primarily driven by favorable development in specialty, property and casualty insurance classes.

Catastrophe losses - current year and prior year were $33.6 million and $1.1 million for the three months ended June 30, 2026 and 2025, respectively. Catastrophe losses for the three months ended June 30, 2026 were driven by the Middle East conflict ($33.6 million). Catastrophe losses for the three months ended June 30, 2025 were driven by severe convective storms ($1.6 million), partially offset by favorable prior year development of $0.5 million.

Acquisition Costs

The acquisition cost ratio for the three months ended June 30, 2026 was 26.5%, compared to 25.9% for the three months ended June 30, 2025, an increase of 0.6 percentage points. The increase was primarily driven by a change in business mix, including an increase in specialty insurance, partially offset by a decrease in property and casualty insurance classes.

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Other Underwriting Expenses and Other Underwriting Expense Ratios

Other underwriting expenses are general and administrative costs incurred by our reportable segments.

Other underwriting expenses were $40.8 million for the three months ended June 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 increase was primarily driven by an increase in personnel costs.

The other underwriting expense ratio for the three months ended June 30, 2026 and 2025 decreased from 14.1% to 12.9%, driven by growth in the premium base, partially offset by an increase in the underlying costs and a decrease in third party fee income.

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Bermuda Segment

Gross Premiums Written

Gross premiums written increased by $43.7 million, or 11.9%, from $367.2 million for the three months ended June 30, 2025 to $411.0 million for the three months ended June 30, 2026, primarily driven by growth in both new and existing business in casualty and specialty reinsurance classes, partially offset by a decrease in property reinsurance and insurance classes, primarily as a result of rate decreases.

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Net Premiums Earned

Net premiums earned increased by $25.4 million, or 9.9%, from $258.0 million for the three months ended June 30, 2025 to $283.4 million for the three months ended June 30, 2026, primarily driven by new business and volume growth in our casualty and specialty reinsurance classes, partially offset by a decrease in our property reinsurance and insurance classes as a result of rate decreases. The increase in casualty reinsurance was primarily driven by general liability and professional liability lines and the increase in specialty reinsurance was primarily driven by marine & energy.

Third Party Fee Income

Third party fee income is generated by certain performance and management fees recognized by Ada Capital Management Limited for services provided to Ada Re, Ltd. and increased by $0.9 million, from $1.2 million for the three months ended June 30, 2025 to $2.1 million for the three months ended June 30, 2026.

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Losses and Loss Adjustment Expenses

Attritional loss ratio - current year for the three months ended June 30, 2026 was 55.7% compared to 54.2% for the three months ended June 30, 2025, an increase of 1.5 percentage points. The increase was primarily driven by a change in business mix, including more proportional casualty reinsurance business.

Attritional loss ratio - prior year for the three months ended June 30, 2026 was an unfavorable 4.6%, compared to an unfavorable 2.0% for the three months ended June 30, 2025, an increase of 2.6 percentage points. The unfavorable attritional loss ratio - prior year for the three months ended June 30, 2026 was primarily driven by unfavorable development on certain casualty reinsurance classes and additional information on one large loss, partially offset by favorable development in property reinsurance classes.

Catastrophe losses - current year and prior year were $16.2 million and $0.4 million for the three months ended June 30, 2026 and 2025, respectively. Catastrophe losses for the three months ended June 30, 2026 were driven by the Middle East conflict ($12.0 million), in addition to unfavorable prior year development of $4.2 million. Catastrophe losses for the three months ended June 30, 2025 were driven by severe convective storms ($8.3 million), partially offset by favorable prior year development of $7.9 million.

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Acquisition Costs

The acquisition cost ratio for the three months ended June 30, 2026 was 23.0%, compared to 22.1% for the three months ended June 30, 2025, an increase of 0.9 percentage points. The increase was primarily driven by a change in business mix, including more proportional business written in our casualty reinsurance classes, partially offset by an increase in ceded commission income.

Other Underwriting Expenses and Other Underwriting Expense Ratios

Other underwriting expenses are general and administrative costs incurred by our reportable segments.

Other underwriting expenses for the three months ended June 30, 2026 were $13.1 million, a decrease of $3.3 million, or 20.3%, compared to $16.5 million for the three months ended June 30, 2025. The decrease 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 June 30, 2026 and 2025 decreased from 5.9% to 3.9%, 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.

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Corporate and Other

Total Net Realized and Unrealized Gains (Losses) on Investments and Net Investment Income (Loss)

The components of total net realized and unrealized gains (losses) on investments and net investment income (loss) are as follows:

(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 $226.5 million and $167.5 million for the three months ended June 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 $115.5 million and $87.1 million for the three months ended June 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 5.1% and 4.4% for the three months ended June 30, 2026 and 2025, respectively.

For the three months ended June 30, 2026, TS Hamilton Fund experienced gains from single name equities trading within the equity market neutral vehicles STV, ESTV and ATV. Gains from single name equities trading were led by the U.S., followed by China onshore and 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 relative value rates vehicle, KTV. Gains from macro trading were led by equities in FTV and were partially offset by losses from macro trading within the scientific discretionary macro vehicle, NTV.

For the three months ended June 30, 2025, TS Hamilton Fund experienced gains from single name equities trading within the equity market neutral vehicles STV, ESTV and ATV. Gains from single name equities trading were led by the U.S., followed by Europe. Gains in TS Hamilton Fund were partially offset 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. Losses in macro trading were led by currencies in both HTV and FTV.

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

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Net Foreign Exchange Gains (Losses)

Our functional currency is the U.S. Dollar. We may conduct routine underwriting operations or invest a portion of our cash and other investable assets in currencies other than U.S. Dollars. Consequently, we may incur foreign exchange gains and losses in our results of operations.

Foreign exchange losses of $2.6 million and $4.5 million for the three months ended June 30, 2026 and 2025, respectively, were primarily driven by the remeasurement of insurance related assets and liabilities denominated in British Pounds, Euro, Japanese Yen, and Australian and Canadian Dollars.

Corporate Expenses

Corporate expenses for the three months ended June 30, 2026 were $13.0 million, compared to $12.9 million for the three months ended June 30, 2025, an increase of $0.2 million, primarily driven by an increase in personnel costs, partially offset by Bermuda substance-based tax credits.

Amortization of Intangible Assets

Amortization of intangible assets of $3.7 million and $4.0 million for the three months ended June 30, 2026 and 2025, respectively, relates to internally developed software and intangible assets acquired in a business combination.

Interest Expense

Interest expense of $4.8 million and $4.7 million for the three months ended June 30, 2026 and 2025, respectively, relates to interest payments and certain administrative fees associated with our term loan and letter of credit facilities. Changes in interest expense are primarily driven by the movement in the Secured Overnight Financing Rate ("SOFR"), which underlies the floating rate associated with the term loan.

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Income Tax Expense (Benefit)

Income tax expense for the three months ended June 30, 2026 was $2.5 million on pre-tax income of $257.3 million, compared to income tax expense of $2.7 million on pre-tax income of $270.5 million for the three months ended June 30, 2025, a decrease of $0.2 million. Income tax expense was primarily driven by withholding taxes on investment income from TS Hamilton Fund.

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Consolidated Results of Operations

The following is a comparison of selected data for our consolidated results of operations:

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The following table summarizes book value per share and balance sheet data:

(1) Third party fee income 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.

(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 $24.1 million and $25.8 million for the six months ended June 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.

(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.

(4) Net investment income (loss) is presented net of investment management fees.

(5) Refer to 'Management’s Discussion and Analysis of Financial Condition and Results of Operations—Consolidated Results of Operations—Corporate and Other' for further details.

Operating Highlights

The following significant items impacted the consolidated results of operations for the six months ended June 30, 2026 and 2025:

Gross premiums written Gross premiums written were $1.8 billion and $1.6 billion for the six months ended June 30, 2026 and 2025, respectively. The increase in gross premiums written was primarily driven by our casualty reinsurance and insurance classes and specialty insurance classes as a result of growth in both new and existing business, partially offset by a decrease in our property reinsurance classes primarily as a result of lower reinstatement premiums and rate decreases for the six months ended June 30, 2026.

Underwriting results The combined ratio was 92.5% and 99.1% for the six months ended June 30, 2026 and 2025, respectively. The decrease was primarily driven by a decrease in the catastrophe loss ratio and other underwriting expense ratio, partially offset by an increase in the attritional loss ratio and acquisition cost ratio.

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Losses and Loss Adjustment Expenses

Attritional loss ratio - current year for the six months ended June 30, 2026 was 53.9% compared to 52.5% for the six months ended June 30, 2025, an increase of 1.4 percentage points. The attritional loss ratio - current year for the six months ended June 30, 2026 was primarily driven by a change in business mix, including more casualty reinsurance and specialty insurance business.

Attritional loss ratio - prior year for the six months ended June 30, 2026 was an unfavorable 1.1% compared to a favorable 1.7% for the six months ended June 30, 2025, an increase of 2.8 percentage points. The attritional loss ratio - prior year for the six months ended June 30, 2026 was primarily driven by additional loss information in relation to certain large losses, including the Baltimore Bridge collapse, and unfavorable development in certain Bermuda casualty classes, partially offset by favorable development in International specialty and property classes and Bermuda property classes. The attritional loss ratio - prior year for the six months ended June 30, 2025 was primarily driven by favorable development in both our Bermuda and International specialty and property classes, partially offset by unfavorable development in certain Bermuda casualty classes.

Catastrophe losses - current year and prior year development were $49.9 million and $152.0 million for the six months ended June 30, 2026 and 2025, respectively. Catastrophe losses for the six months ended June 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 six months ended June 30, 2025 were driven by the California wildfires ($159.7 million) and severe convective storms ($9.9 million), partially offset by favorable prior year development of $17.6 million.

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Total Net Realized and Unrealized Gains (Losses) on Investments and Net Investment Income (Loss)

The components of total net realized and unrealized gains (losses) on investments and net investment income (loss) are as follows:

(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 $403.0 million and $371.4 million for the six months ended June 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 $208.5 million and $190.7 million for the six months ended June 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 9.6% and 10.1% for the six months ended June 30, 2026 and 2025, respectively.

For the six months ended June 30, 2026, TS Hamilton Fund experienced gains from single name equities trading within the equity market neutral vehicles STV, ESTV and ATV. Gains from single name equities trading were led by the U.S., followed by China onshore and Europe. TS Hamilton Fund also experienced gains from macro trading within the systematic macro vehicle, FTV, the relative value macro vehicle, HTV, and the scientific discretionary macro vehicle, NTV. Gains from macro trading were led by commodities in FTV and were partially offset by losses within the relative value rates vehicle, KTV.

For the six months ended June 30, 2025, TS Hamilton Fund experienced gains from single name equities trading within the equity market neutral vehicles STV, ESTV and ATV. Gains from single name equities trading were led by the U.S., followed by East Asia. TS Hamilton Fund also experienced gains from macro trading within the scientific discretionary macro vehicle, NTV. Gains in TS Hamilton Fund were partially offset by losses from macro trading within the systematic macro vehicle, FTV, the relative value macro vehicle, HTV, and the relative value rates vehicle, KTV. Losses in macro trading were led by currencies in both HTV and FTV.

Total net realized and unrealized gains (losses) on investments and net investment income (loss) - other, returned income of $26.4 million and $125.4 million for the six months ended June 30, 2026 and 2025, respectively. Income for the six months ended June 30, 2026 was driven by investment income on a larger portfolio of higher yielding assets, partially offset by negative mark-to-market returns. Income for the six months ended June 30, 2025 was primarily driven by investment income and positive mark-to-market returns.

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International Segment

Gross Premiums Written

Gross premiums written increased by $148.2 million, or 20.7%, from $714.8 million for the six months ended June 30, 2025 to $863.0 million for the six months ended June 30, 2026, primarily driven by growth in both new and existing business in casualty and specialty insurance classes.

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Net Premiums Earned

Net premiums earned increased by $99.6 million, or 20.2%, from $493.8 million for the six months ended June 30, 2025 to $593.4 million for the six months ended June 30, 2026. The increase was primarily driven by growth in our specialty and casualty insurance and specialty reinsurance 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 casualty insurance growth was primarily driven by U.S. excess and surplus lines and professional lines.

Third Party Fee Income

Third party fee income decreased by $3.8 million, from $8.2 million for the six months ended June 30, 2025 to $4.4 million for the six months ended June 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.

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Losses and Loss Adjustment Expenses

Attritional loss ratio - current year for the six months ended June 30, 2026 was 53.0% compared to 52.0% for the six months ended June 30, 2025, an increase of 1.0 percentage points. The increase was primarily driven by a change in business mix, including more specialty insurance business.

Attritional loss ratio - prior year for the six months ended June 30, 2026 was a favorable 1.7% compared to a favorable 3.3% for the six months ended June 30, 2025, an increase of 1.6 percentage points. The favorable attritional loss ratio - prior year for the six months ended June 30, 2026 was primarily driven by favorable development in specialty, property and casualty insurance classes, partially offset by additional loss information in relation to the Baltimore Bridge collapse.

Catastrophe losses - current year and prior year were $33.6 million and $30.2 million for the six months ended June 30, 2026 and 2025, respectively. Catastrophe losses for the six months ended June 30, 2026 were driven by the Middle East conflict ($33.6 million). Catastrophe losses for the six months ended June 30, 2025 were driven by the California wildfires ($29.0 million) and severe convective storms ($1.6 million), partially offset by favorable prior year development of $0.4 million.

Acquisition Costs

The acquisition cost ratio for the six months ended June 30, 2026 was 27.2%, compared to 26.0% for the six months ended June 30, 2025, an increase of 1.2 percentage points. The increase was primarily driven by a change in business mix, including an increase in specialty insurance.

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Other Underwriting Expenses and Other Underwriting Expense Ratios

Other underwriting expenses are general and administrative costs incurred by our reportable segments.

Other underwriting expenses were $82.1 million for the six months ended June 30, 2026, an increase of $6.9 million, or 9.2%, compared to $75.1 million for the six months ended June 30, 2025. The increase was primarily driven by an increase in personnel costs.

The other underwriting expense ratio for the six months ended June 30, 2026 and 2025 decreased from 13.6% to 13.1% driven by growth in the premium base, partially offset by an increase in the underlying costs and a decrease in third party fee income.

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Bermuda Segment

Gross Premiums Written

Gross premiums written increased by $67.6 million, or 8.0%, from $840.6 million for the six months ended June 30, 2025 to $908.2 million for the six months ended June 30, 2026, primarily driven by growth in both new and existing business in casualty reinsurance classes, partially offset by a decrease in property reinsurance classes as a result of lower reinstatement premiums and rate decreases.

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Net Premiums Earned

Net premiums earned increased by $46.8 million, or 9.1%, from $516.3 million for the six months ended June 30, 2025 to $563.1 million for the six months ended June 30, 2026, primarily driven by new business and volume growth in our casualty reinsurance classes, partially offset by a decrease in our property reinsurance classes as a result of lower reinstatement premiums and rate decreases. The increase in casualty reinsurance was primarily driven by general liability lines.

Third Party Fee Income

Third party fee income is generated by certain performance and management fees recognized by Ada Capital Management Limited for services provided to Ada Re, Ltd. and increased by $4.8 million, from $1.5 million for the six months ended June 30, 2025 to $6.3 million for the six months ended June 30, 2026.

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Losses and Loss Adjustment Expenses

Attritional loss ratio - current year for the six months ended June 30, 2026 was 54.9% compared to 53.0% for the six months ended June 30, 2025, an increase of 1.9 percentage points. The increase was primarily driven by a change in business mix, including more proportional casualty reinsurance business.

Attritional loss ratio - prior year for the six months ended June 30, 2026 was an unfavorable 4.1% compared to a favorable 0.1% for the six months ended June 30, 2025, an increase of 4.2 percentage points. The unfavorable attritional loss ratio - prior year for the six months ended June 30, 2026 was primarily driven by additional loss information in relation to certain large losses, including the Baltimore Bridge collapse, and unfavorable development in certain casualty reinsurance classes, partially offset by favorable development in property reinsurance classes.

Catastrophe losses - current year and prior year were $16.2 million and $121.9 million for the six months ended June 30, 2026 and 2025, respectively. Catastrophe losses for the six months ended June 30, 2026 were driven by the Middle East conflict ($12.0 million), in addition to unfavorable prior year development of $4.2 million. Catastrophe losses for the six months ended June 30, 2025 were driven by the California wildfires ($130.7 million) and severe convective storms ($8.3 million), partially offset by favorable prior year development of $17.1 million.

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Acquisition Costs

The acquisition cost ratio for the six months ended June 30, 2026 was 22.8%, compared to 21.5% for the six months ended June 30, 2025, an increase of 1.3 percentage points. The increase was driven by a change in business mix, including more proportional business written in our casualty reinsurance classes, partially offset by an increase in ceded commission income.

Other Underwriting Expenses and Other Underwriting Expense Ratios

Other underwriting expenses are general and administrative costs incurred by our reportable segments.

Other underwriting expenses for the six months ended June 30, 2026 were $22.2 million, a decrease of $8.4 million, or 27.3%, compared to $30.6 million for the six months ended June 30, 2025. The decrease was primarily driven by Bermuda substance-based tax credits, partially offset by an increase in personnel costs.

The other underwriting expense ratio for the six months ended June 30, 2026 and 2025 decreased from 5.6% to 2.8%, 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.

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Corporate and Other

Total Net Realized and Unrealized Gains (Losses) on Investments and Net Investment Income (Loss)

The components of total net realized and unrealized gains (losses) on investments and net investment income (loss) are as follows:

(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 $403.0 million and $371.4 million for the six months ended June 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 $208.5 million and $190.7 million for the six months ended June 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 9.6% and 10.1% for the six months ended June 30, 2026 and 2025, respectively.

For the six months ended June 30, 2026, TS Hamilton Fund experienced gains from single name equities trading within the equity market neutral vehicles STV, ESTV and ATV. Gains from single name equities trading were led by the U.S., followed by China onshore and Europe. TS Hamilton Fund also experienced gains from macro trading within the systematic macro vehicle, FTV, the relative value macro vehicle, HTV, and the scientific discretionary macro vehicle, NTV. Gains from macro trading were led by commodities in FTV and were partially offset by losses within the relative value rates vehicle, KTV.

For the six months ended June 30, 2025, TS Hamilton Fund experienced gains from single name equities trading within the equity market neutral vehicles STV, ESTV and ATV. Gains from single name equities trading were led by the U.S., followed by East Asia. TS Hamilton Fund also experienced gains from macro trading within the scientific discretionary macro vehicle, NTV. Gains in TS Hamilton Fund were partially offset by losses from macro trading within the systematic macro vehicle, FTV, the relative value macro vehicle, HTV, and the relative value rates vehicle, KTV. Losses in macro trading were led by currencies in both HTV and FTV.

Total net realized and unrealized gains (losses) on investments and net investment income (loss) - other, returned income of $26.4 million and $125.4 million for the six months ended June 30, 2026 and 2025, respectively. Income for the six months ended June 30, 2026 was driven by investment income on a larger portfolio of higher yielding assets, partially offset by negative mark-to-market returns. Income for the six months ended June 30, 2025 was primarily driven by investment income and positive mark-to-market returns.

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Net Foreign Exchange Gains (Losses)

Our functional currency is the U.S. Dollar. We may conduct routine underwriting operations or invest a portion of our cash and other investable assets in currencies other than U.S. Dollars. Consequently, we may incur foreign exchange gains and losses in our results of operations.

Foreign exchange gains of $1.9 million and losses of $7.0 million for the six months ended June 30, 2026 and 2025, respectively, were primarily driven by the remeasurement of insurance related assets and liabilities denominated in British Pounds, Euro, Japanese Yen, and Australian and Canadian Dollars.

Corporate Expenses

Corporate expenses for the six months ended June 30, 2026 were $24.1 million, compared to $25.8 million for the six months ended June 30, 2025, a decrease of $1.7 million. The decrease was primarily driven by the impact of the Bermuda substance-based tax credits, partially offset by an increase in personnel costs.

Amortization of Intangible Assets

Amortization of intangible assets of $7.7 million and $7.9 million for the six months ended June 30, 2026 and 2025, respectively, relates to internally developed software and intangible assets acquired in a business combination.

Interest Expense

Interest expense of $9.5 million and $10.3 million for the six months ended June 30, 2026 and 2025, respectively, relates to interest payments and certain administrative fees associated with our term loan and letter of credit facilities. The decrease in interest expense is primarily driven by the movement in the Secured Overnight Financing Rate ("SOFR"), which underlies the floating rate associated with the term loan.

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Income Tax Expense (Benefit)

Income tax expense for the six months ended June 30, 2026 was $4.8 million on pre-tax income of $476.6 million, compared to income tax expense of $5.9 million on pre-tax income of $454.9 million for the six months ended June 30, 2025, a decrease of $1.1 million. Income tax expense was primarily driven by withholding taxes on investment income from TS Hamilton Fund.

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Key Operating and Financial Metrics

The Company has identified the following metrics as key measures of the Company’s performance:

Book Value per Common Share

Management believes that book value is an important indicator of value provided to common shareholders and aligns the Company’s and most investors’ long term objectives. We calculate book value per common share as total common shareholders’ equity divided by the total number of common shares outstanding at the point in time.

Book value per common share was $28.91 at June 30, 2026, a $0.41 or 1.4% increase from the Company’s book value per common share of $28.50 at December 31, 2025 and a $2.41 or 8.5% increase from $28.50 when incorporating the impact of the special dividend paid to common shareholders in the six months ended June 30, 2026.

The increase in book value per common share plus accumulated dividends was primarily driven by the Company’s net income attributable to common shareholders of $277.3 million for the six months ended June 30, 2026. See Note 10, Share Capital in the accompanying unaudited condensed consolidated financial statements for further details.

Tangible Book Value per Common Share

Management believes that tangible book value is an important indicator of value provided to common shareholders and aligns the Company’s and most investors’ long term objectives. We calculate tangible book value per common share as total common shareholders’ equity less intangible assets, divided by the total number of common shares outstanding at the point in time.

Tangible book value per common share was $28.07 at June 30, 2026, a $0.45 or 1.6% increase from the Company’s tangible book value per common share of $27.62 at December 31, 2025 and a $2.45 or 8.9% increase from $27.62 when incorporating the impact of the special dividend paid to common shareholders in the six months ended June 30, 2026.

The increase in book value per common share plus accumulated dividends was primarily driven by the Company’s net income attributable to common shareholders of $277.3 million for the six months ended June 30, 2026. See Note 10, Share Capital in the accompanying unaudited condensed consolidated financial statements for further details.

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Return on Average Common Shareholders' Equity

Management believes that return on average common shareholders’ equity ("ROACE") is an important indicator of the Company’s profitability and financial efficiency. We calculate ROACE by dividing net income (loss) attributable to common shareholders by average common shareholders' equity for the corresponding period.

ROACE was 5.2% for the three months ended June 30, 2026, compared to 7.6% for the three months ended June 30, 2025. The decrease was driven by the higher average common shareholders' equity and lower net income attributable to common shareholders reported as at and for the three months ended June 30, 2026, respectively.

ROACE was 9.8% for the six months ended June 30, 2026, compared to 11.0% for the six months ended June 30, 2025. The decrease was driven by the higher average common shareholders' equity, partially offset by the higher net income attributable to common shareholders reported as at and for the six months ended June 30, 2026, respectively.

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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 following table reconciles underwriting income (loss) to net income (loss), the most directly comparable GAAP financial measure:

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 performance and management fees earned by the Bermuda segment that were generated by our third party capital manager, Ada Capital Management Limited, and fees earned by the International segment for management services provided to consortia and third party syndicates. We believe that this measure is a relevant component of our underwriting income (loss).

The following table reconciles third party fee income to other income (loss), the most directly comparable GAAP financial measure:

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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, 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 directly comparable GAAP financial measure to other underwriting expenses, also includes corporate expenses.

The following table 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.

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Financial Condition, Liquidity and Capital Resources

Financial Condition

Investment Philosophy

The Company maintains two segregated investment portfolios: a fixed maturities and short-term investments trading portfolio and an investment in TS Hamilton Fund.

Our high quality and liquid fixed maturities and short-term investments trading portfolio is structured to focus primarily on the preservation of capital and the availability of liquidity to meet the Company’s claims obligations, to be well diversified across market sectors, and to generate relatively attractive returns on a risk-adjusted basis over time. Our investments are subject to market-wide risks and fluctuations, as well as to risks inherent in particular securities.

The Company also invests in TS Hamilton Fund, a Delaware limited liability company. Hamilton Re has agreed to use its reasonable best efforts to maintain an investment in TS Hamilton Fund in an amount not less than the lesser of (i) $1.8 billion or (ii) 60% of Hamilton Group’s net tangible assets (the "Minimum Commitment Amount"). Hamilton Re has the ability to withdraw capital from the TS Hamilton Fund under a two‑tier structure that distinguishes between amounts in excess of the Minimum Commitment Amount ("Sub‑Series A Interests") and amounts at or below that level ("Sub‑Series B Interests"). Hamilton Re may withdraw Sub‑Series A Interests on a quarterly basis with at least 55 days’ prior notice, and may withdraw Sub‑Series B Interests on a monthly basis, subject to a six‑month notice requirement and monthly limits, including a cap of one-twelfth of such interests per month.

The TS Hamilton Fund investment strategy is focused on delivering non-market correlated investment income and total return through all market cycles while maintaining appropriate portfolio liquidity and credit quality to meet the requirements of customers, rating agencies and regulators. Two Sigma, the investment manager of the TS Hamilton Fund, is an investment adviser registered with the U.S. Securities and Exchange Commission specializing in quantitative analysis.

Cash and Investments

At June 30, 2026 and December 31, 2025, total cash and investments was $6.1 billion and $6.2 billion, respectively. However, a significant portion of the total cash and investments balances held were invested in TS Hamilton Fund as collateral for the investments held by the underlying trading vehicles, as shown in the tables under the "TS Hamilton Fund" discussion.

Total cash and investments decreased from $6.2 billion at December 31, 2025 to $6.1 billion at June 30, 2026. The decrease was primarily driven by payment of a special dividend, partially offset by positive investment returns on the TS Hamilton Fund and the continued deployment of cash into, and positive investment returns on, our fixed maturities and short-term investments trading portfolio.

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Fixed Maturity and Short-term Investments - Trading

The Company’s fixed maturity trading portfolio and short-term investments are as follows:

The fair value of the Company’s fixed maturity trading portfolio and short-term investments was $3.5 billion and $3.4 billion at June 30, 2026 and December 31, 2025, respectively.

Short-term investments at June 30, 2026 and December 31, 2025 of $356.5 million and $200.5 million, respectively, include $356.4 million and $199.0 million, respectively, held within TS Hamilton Fund. The cash and short-term investment balances within TS Hamilton Fund are not managed by the Company, nor can they be removed from TS Hamilton Fund as they support the underlying investment strategies within the seven trading vehicles. The balance may fluctuate significantly from period to period as a result of movements in the underlying funds. See the following discussion for further details on assets within TS Hamilton Fund.

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The fair values and weighted-average credit ratings of our fixed maturity trading portfolio and short-term investments by type were as follows:

The average credit quality, the average yield to maturity and the expected average duration of the Company’s fixed maturities and short-term investments trading portfolio, excluding short-term investments held by the TS Hamilton Fund, were as follows:

At June 30, 2026 and December 31, 2025, 100% of the Company’s fixed maturities and short-term investments trading portfolio was rated investment grade (Baa3 or higher) by third party rating services. The average credit quality of the Company’s fixed maturities and short-term investments trading portfolio, excluding short-term investments held by the TS Hamilton Fund, at June 30, 2026 and December 31, 2025, was A1 and Aa3, respectively.

The average yield to maturity on the Company’s fixed maturities and short-term investments trading portfolio increased to 4.7% at June 30, 2026 from 4.1% at December 31, 2025.

The expected average duration of the Company’s fixed maturities and short-term investments trading portfolio was 4.0 years and 3.4 years at June 30, 2026 and December 31, 2025, respectively.

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TS Hamilton Fund

TS Hamilton Fund invests in Two Sigma Funds ("Two Sigma Funds"), which are stated at their estimated fair values, which generally represent the Company’s proportionate interest in the members’ equity of the Two Sigma Funds as reported by the respective funds based on the net asset value ("NAV") provided by the fund administrator. The Company accounts for its investment in Two Sigma Funds under the variable interest model at NAV as a practical expedient for fair value in the consolidated balance sheet.

The Company owns the following interest in each of the Two Sigma Funds:

Although Two Sigma has broad discretion to allocate invested assets to different opportunities, the current strategy is focused on highly diversified liquid positions in global equities, futures and foreign exchange markets. Through its investments in the Two Sigma Funds, we seek to achieve absolute dollar-denominated returns on a substantial capital base, primarily by combining multiple hedged and leveraged systematic and non-systematic investment strategies with proprietary risk management and execution techniques. These strategies include, but are not limited to, technical and statistically-based, fundamental-based, event-based, market condition-based and spread-based strategies as well as contributor-based and/or sentiment-based strategies and blended strategies.

• STV primarily utilizes systematic strategies to trade exchange-traded funds.
• ESTV primarily utilizes systematic strategies to trade U.S. listed and non-U.S.-listed equity securities, swap contracts, money market funds, government debt securities, futures and foreign currency forward contracts.
• ATV primarily utilizes systematic strategies to trade a diversified, global, equity market neutral portfolio, predominantly of equity securities, equity-related derivatives and other related instruments.
• FTV primarily utilizes systematic macro strategies to trade exchange traded funds, exchange memberships, government debt securities, money market funds, option contracts, swap contracts, futures and forward contracts.
• HTV primarily utilizes systematic strategies and non-systematic discretionary strategies to trade futures, futures options, foreign currency spot, forward and option contracts, exchange-traded products ("ETPs") and ETP options, debt securities, and various types of derivatives and other instruments.
• NTV primarily utilizes non-systematic discretionary macro strategies that combine human discretion with quantitative analysis for purposes of trading globally across various asset classes.
• KTV primarily utilizes non-systematic discretionary strategies that combine human discretion with quantitative analysis to trade futures, futures options, foreign currency spot, forward and option contracts, ETPs and ETP options, debt securities, and various types of derivatives and other instruments.

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The Company’s investments in Two Sigma Funds are as follows:

The increase in the total fair value of the Company’s investments in Two Sigma Funds from $1.6 billion at December 31, 2025 to $1.8 billion at June 30, 2026 is primarily driven by investment gains, asset allocations and collateral management within TS Hamilton Fund. The total net assets managed in TS Hamilton Fund represent our investment in and exposure to Two Sigma Funds’ investment strategies. However, as part of Two Sigma’s collateral management processes, any capital not required to be held within one of the specific trading vehicles is held in cash or short-term investments within TS Hamilton Fund as shown in the following table. The cash and short-term investment balances are not managed by the Company, nor can they be removed from TS Hamilton Fund as they support the underlying investment strategies within the seven trading vehicles.

The following table represents the total assets and total liabilities of TS Hamilton Fund. Creditors or beneficial interest holders of TS Hamilton Fund have no recourse to the general credit of the Company as the Company’s obligation is limited to the amount of its committed investment.

Total net assets in TS Hamilton Fund were $2.5 billion and $2.2 billion at June 30, 2026 and December 31, 2025, respectively.

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Liquidity and Capital Resources

Liquidity

Liquidity is a measure of a company’s ability to generate cash flows sufficient to meet the short-term and long-term cash requirements of its business operations. The Company manages liquidity at the holding company and operating subsidiary level.

Management believes that its significant cash flows from operations and high quality liquid investment portfolio will provide sufficient liquidity for the foreseeable future. At June 30, 2026 and December 31, 2025, total unrestricted cash and cash equivalents were $717.3 million and $1.1 billion, respectively, and total restricted cash and cash equivalents were $111.6 million and $109.7 million, respectively.

Holding Company

As a holding company, Hamilton Insurance Group, Ltd. has no operations of its own and its assets consist primarily of investments in its subsidiaries. Accordingly, Hamilton Group’s future cash flows depend on the availability of dividends or other statutorily permissible distributions, such as returns of capital, from its subsidiaries. The ability to pay such dividends and/or distributions is limited by the applicable laws and regulations of the various countries and states in which the Company’s subsidiaries operate (refer to Note 17, Statutory Requirements in the audited consolidated financial statements included in our Form 10-K for the year ended December 31, 2025 for further details), as well as the need to maintain capital levels to adequately support insurance and reinsurance operations, and to preserve financial strength ratings issued by independent rating agencies. Hamilton Group also maintains capital maintenance agreements with certain insurance subsidiaries, designed to support regulatory and rating agency capital requirements. Under these agreements, Hamilton Group may be required to contribute capital if a subsidiary’s capital levels fall below specified regulatory or rating agency thresholds.

During the six months ended June 30, 2026 and 2025, Hamilton Group received $306.0 million and $115.5 million, respectively, of distributions from its subsidiaries. The Company’s primary use of funds includes common share repurchases, interest payments on debt and credit facilities, capital investments in subsidiaries, and payment of corporate operating expenses. The Company also declared and paid a special dividend of $2.00 per common share, or $199.5 million, in the six months ended June 30, 2026. Common share repurchases may be conducted through open market repurchases and/or privately negotiated transactions. See Note 10, Share Capital, in the accompanying unaudited condensed consolidated financial statements for further detail of common share repurchases in the six months ended June 30, 2026. Management believes the dividend distribution capacity of Hamilton Group’s subsidiaries, which was estimated at $620.1 million at December 31, 2025, will provide the Company with sufficient liquidity for the foreseeable future.

Operating Subsidiaries

Hamilton Group’s operating subsidiaries primarily derive cash from the net inflow of premiums less claim payments related to underwriting activities and from net investment income. Historically, these cash receipts have been sufficient to fund the operating expenses of these subsidiaries, as well as to fund dividend payments to the Company. The subsidiaries’ remaining cash flows are generally invested in the fixed maturities and short-term investments trading portfolio and used to fund common share repurchases or acquisitions.

The operating subsidiaries’ insurance and reinsurance business inherently provides liquidity, as premiums are received in advance (sometimes substantially in advance) of the time losses are paid. However, the amount of cash required to fund loss payments can fluctuate significantly from period to period, due to the low frequency and high severity nature of certain types of business written. As such, cash flows from operating activities may vary significantly between periods.

The payment of dividends by operating subsidiaries is, under certain circumstances, limited by the applicable laws and regulations in the various jurisdictions in which the subsidiaries operate. In addition, insurance laws require the insurance subsidiaries to maintain certain measures of solvency and liquidity. Each of the Company’s insurance subsidiaries and branches exceeded the minimum solvency, capital and surplus requirements in their applicable jurisdictions at December 31, 2025. Certain of the subsidiaries and branches are required to file Financial Condition Reports ("FCRs"), with their regulators, which provide details on solvency and financial performance. Where required, these FCRs are posted on the Company’s website.

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The regulations governing the Company’s principal operating subsidiaries’ ability to pay dividends and to maintain certain measures of solvency and liquidity are discussed in Note 17, Statutory Requirements in the Company’s audited consolidated financial statements as included in our Form 10-K for the year ended December 31, 2025.

Consolidated Cash Flows

Consolidated cash flows from operating, investing and financing activities were as follows:

Net cash provided by (used in) operating activities was $226.1 million and $253.3 million in the six months ended June 30, 2026 and 2025, respectively. Cash inflows from insurance and reinsurance operations typically include premiums, net of acquisition costs, and reinsurance recoverables. Cash outflows principally include payments of losses and loss expenses, payments of premiums to reinsurers and operating expenses. Cash provided by operating activities fluctuates due to timing differences between the collection of premiums and reinsurance recoverables and the payment of losses and loss adjustment expenses, and the payment of premiums to reinsurers.

Net cash provided by (used in) investing activities was $(186.8) million and $(140.8) million in the six months ended June 30, 2026 and 2025, respectively, primarily driven by the timing of investing activities and the net proceeds of turnover, asset allocations within the TS Hamilton Fund, and our fixed maturity and short-term investments.

Net cash provided by (used in) financing activities was $(375.9) million and $(163.8) million in the six months ended June 30, 2026 and 2025, respectively. Net cash used in financing activities for the six months ended June 30, 2026 was primarily driven by the special dividend, incentive allocations paid to TS Hamilton Fund and share repurchases. Net cash used in financing activities for the six months ended June 30, 2025 was primarily driven by incentive allocations paid to TS Hamilton Fund and share repurchases. See Note 10, Share Capital in the accompanying unaudited condensed consolidated financial statements for further details of common share repurchases for the six months ended June 30, 2026 and 2025.

We believe that annual positive cash flows from operating activities will be sufficient to cover claims payments, absent a series of additional large catastrophic losses. However, should claim payment obligations accelerate beyond the Company’s ability to fund payments from operating cash flows, the Company would utilize cash and cash equivalent balances and/or liquidate a portion of its fixed maturities and short-term investments trading portfolio and/or access certain credit facilities. The fixed maturities and short-term investments trading portfolio is heavily weighted towards conservative, high quality and highly liquid securities.

In addition, if necessary, we have the ability to liquidate a portion of our investment portfolio in the TS Hamilton Fund. Hamilton Re may withdraw its investment under a two‑tier withdrawal structure that distinguishes between amounts in excess of the Minimum Commitment Amount ("Sub-Series A Interests") and amounts at or below that level ("Sub-Series B Interests"). Sub-Series A Interests may be withdrawn on a quarterly basis with at least 55 days’ prior notice. Sub-Series B Interests may be withdrawn on a monthly basis, subject to a six‑month notice requirement and monthly withdrawal limitations, including a maximum withdrawal of one-twelfth of such interests per month.

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Management expects that, if necessary, the full value of cash, fixed income and short-term investments at June 30, 2026 could be available in one to three business days under normal market conditions, except for $786.1 million of restricted cash and investments which primarily support the Company’s obligations in regulatory jurisdictions where it operates as a non-admitted carrier (refer to Note 3, Investments in the accompanying unaudited condensed consolidated financial statements) and $255.5 million of restricted cash and investments which primarily support the Company’s letter of credit facilities (refer to Note 9, Debt and Credit Facilities in the accompanying unaudited condensed consolidated financial statements).

Capital Resources

Management monitors the Company’s capital adequacy on a regular basis and seeks to adjust its capital according to the needs of the business. In particular, the Company requires capital sufficient to meet or exceed the capital adequacy ratios established by rating agencies for maintenance of appropriate financial strength ratings and the capital adequacy tests performed by regulatory authorities. From time to time, rating agencies and regulatory authorities may make changes in their models and methodologies, which could increase the amount of capital the Company requires. The Company may seek to raise additional capital or return capital to shareholders through some combination of common share repurchases and cash dividends. In the normal course of operations, management may from time to time evaluate additional share or debt issuances given prevailing market conditions and capital management strategies. In addition, the Company enters into agreements with financial institutions to obtain letter of credit facilities for the benefit of its operating subsidiaries to support their business operations. Management believes that the Company holds sufficient capital to allow it to take advantage of market opportunities and to maintain its financial strength ratings and comply with various local statutory regulations.

The following table summarizes our consolidated total capital:

The Company’s consolidated shareholders' equity was $2.9 billion at June 30, 2026, a 1.0% increase compared to $2.8 billion at December 31, 2025. The primary driver of the increase in total capital was the Company’s net income attributable to common shareholders of $277.3 million for the six months ended June 30, 2026, partially offset by the special dividend and share repurchases (see Note 10, Share Capital in the accompanying unaudited condensed consolidated financial statements for further details).

Debt

On June 10, 2025, Hamilton Group entered into a $150 million term loan credit arrangement (the "Facility") with various lenders as arranged by Wells Fargo Securities, LLC. The Facility will be used to refinance the indebtedness outstanding under the Existing Loan Agreement. All or a portion of the loan issued under the Facility bears interest, at the option of Hamilton Group, at either (a) a base rate plus an applicable margin or (b) the Adjusted Term Secured Overnight Financing Rate ("SOFR") plus an applicable margin, in each case with the applicable margin determined with reference to the Company's long term issuer default rating as assigned by Fitch. The Facility matures on June 9, 2028, unless accelerated pursuant to the terms of the Facility, and it contains usual and customary representations, warranties, conditions and covenants for bank loan facilities of this type. The Facility also includes financial covenants, including a financial strength rating test, a minimum consolidated tangible net worth test and a maximum consolidated indebtedness to total capitalization ratio.

The following table presents the gross outstanding loan balance, loan fair value and unamortized loan issuance costs:

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Debt issuance costs are amortized over the period during which the Facility is outstanding, as an offset to net investment income (loss). The Company amortized debt issuance costs of $0.1 million or less in each of the three and six months ended June 30, 2026 and 2025. The Company’s debt is classified as Level 3 within the fair value hierarchy because it is valued using an income approach, which utilizes a discounted cash flow technique that considers the credit profile of the Company.

Common Shares

The Company’s authorized and issued share capital is comprised as follows:

On November 4, 2025, the Board of Directors authorized the repurchase of the Company's common shares in the aggregate amount of $150.0 million, in addition to remaining amounts under the prior authorization (collectively, the "Authorization"), under which the Company may repurchase shares through open market repurchases and/or privately negotiated transactions. The Authorization will expire when the Company has repurchased the full value of shares authorized, unless terminated earlier by the Board of Directors. All shares repurchased under the Authorization were subsequently cancelled. As of June 30, 2026, $136.7 million remained available for repurchase under the Authorization.

In general, holders of Class A common shares and Class B common shares have one vote for each common share held while the Class C common shares have no voting rights, except as required by law. However, each holder of Class A common shares and Class B common shares is limited to voting (directly, indirectly or constructively, as determined for U.S. federal income tax purposes) that number of common shares equal to 9.5% of the total combined voting power of all classes of shares of the Company (or, in the case of a class vote by the holders of our Class B common shares, such as in respect of the election or removal of directors other than for directors who are appointed by certain shareholders pursuant to the Shareholders Agreement and our Bye-laws, an amount calculated by multiplying (a) 9.5% and (b) the quotient of dividing (x) the total number of directors by (y) the number of directors elected by holders of Class B common shares). In addition, the Board of Directors may, in its absolute discretion, limit a shareholder’s voting rights when it deems it appropriate to do so to avoid certain material adverse tax, legal or regulatory consequences to the Company, any subsidiary of the Company, or any direct or indirect shareholder or its affiliates.

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Credit Facilities

The Company has several available letter of credit ("LOC") facilities and a revolving loan facility provided by commercial banks. The LOC facilities are utilized to provide collateral to reinsureds of Hamilton Re and its affiliates to the extent required under insurance and reinsurance agreements and to support capital requirements at Lloyd’s.

On December 5, 2018 and December 27, 2018, Hamilton Re entered into a Master Agreement for Issuance of Payment Instruments and a Facility Letter for Issuance of Payment Instruments with CitiBank Europe Plc ("CitiBank Europe"), under which CitiBank Europe agreed to provide an uncommitted secured letter of credit facility for the issuance of standby letters of credit or similar instruments in multiple currencies. On November 15, 2024, letter of credit capacity under this facility was increased to $250 million. At all times during which it is a party to the facility, Hamilton Re is obligated to pledge to CitiBank Europe cash and/or securities with a value that equals or exceeds the aggregate face amount of its then-outstanding letters of credit. The Master Agreement contains events of default customary for facilities of this type. In the facility letter, Hamilton Re makes representations and warranties that are customary for facilities of this type and agrees that it will comply with certain informational and other undertakings.

On June 10, 2025, Hamilton Group and Hamilton Re entered into a $450 million credit agreement with a syndication of lenders (the "Unsecured Facility"). Under the Unsecured Facility, the lenders have agreed to provide up to an aggregate of $450 million of letter of credit capacity for Hamilton Re, up to $150 million of which may be utilized for revolving loans to be issued to Hamilton Group. At June 30, 2026, there were no loan amounts outstanding under the Unsecured Facility. Letters of credit issued under the Unsecured Facility bear interest at a rate determined by Hamilton Group’s long-term issuer default rating, while revolving loans, if drawn, accrue interest at the option of Hamilton Group at either (a) a base rate plus an applicable margin or (b) Adjusted Term SOFR plus an applicable margin. In each case, the applicable margin is determined based on Hamilton Group’s long-term issuer default rating as assigned by Fitch. Currently, any letters of credit issued under the facility bear interest at a rate of 125 basis points. Revolving loans, if issued, are subject to a fee equal to the prime rate plus 50 basis points or Adjusted Term SOFR plus a margin of 150 basis points. To the extent such loans are issued, the available letter of credit capacity shall decrease proportionally, such that the aggregate credit exposure for the lenders under the Unsecured Facility is $450 million. Amounts unutilized under the Unsecured Facility are subject to a fee based upon Hamilton Group's long-term issuer default rating as assigned by Fitch, currently equal to 17.5 basis points. The Unsecured Facility is subject to representations and warranties, affirmative and negative covenants and events of default that the Company considers customary for similar facilities. The Unsecured Facility also includes financial covenants, including a financial strength rating test, a minimum consolidated tangible net worth test and a maximum consolidated indebtedness to total capitalization ratio. Capacity is provided by Wells Fargo, National Association, Truist Bank, Commerzbank AG, New York Branch, Citizens Bank, N.A., HSBC Bank USA, National Association, and Barclays Bank PLC. Unless renewed or otherwise terminated in accordance with its terms, the Unsecured Facility has a maturity date of June 9, 2028.

On October 23, 2025, Hamilton Re amended its letter of credit facility agreement with UBS AG ("UBS") under which UBS and certain of its affiliates agreed to make available to Hamilton Re a secured letter of credit facility in an amount that is equal to the greater of (i) $25 million and (ii) the LOC amount issued and outstanding, provided that the amount shall not at any time be greater than $75 million, for a term that will expire on October 23, 2026. The facility bears a fee of 140 basis points on the total available capacity.

In addition, on October 20, 2025, Hamilton Re amended the unsecured letter of credit facility agreement that it utilizes to provide Funds at Lloyd's ("FAL") ("FAL LOC Facility") to support the FAL requirements of Syndicate 4000. Capacity is provided by ING Bank N.V., London Branch, Commerzbank AG, New York Branch, and Deutsche Bank AG, London Branch. The FAL LOC Facility was renewed in the amount of $260 million for a term that expires on December 31, 2029. The facility bears a fee of 150 basis points on the utilized amount.

The Company’s obligations under its credit facilities require Hamilton Group, Hamilton Re and the other parties thereto to comply with various financial and reporting covenants. All applicable entities were in compliance with all such covenants at June 30, 2026.

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Certain of the Company's credit facilities are secured by pledged interests in the TS Hamilton Fund, the Company's fixed income security portfolio, or cash. The Company’s credit facilities and associated securities pledged, were as follows:

(1) Cash pledged as security under letter of credit and revolving loan facilities is included in restricted cash securing other underwriting obligations under Pledged Assets in Note 3, Investments.

Financial Strength Ratings

The Company’s principal insurance and reinsurance operating subsidiaries are assigned financial strength ratings from various internationally recognized rating agencies registered with the SEC as Nationally Recognized Statistical Rating Organizations. Each agency's ratings are publicly announced, defined and available directly from the agencies' websites.

Financial strength ratings represent the independent opinions of the rating agencies as to the relative creditworthiness of a company and its capacity to meet the obligations of its insurance and reinsurance contracts. Independent ratings are one of the important factors that establish a competitive position in insurance and reinsurance markets. These ratings are based on factors considered by the rating agencies to be relevant to policyholders, agents and intermediaries and are not directed toward the protection of investors. Ratings are not recommendations to buy, sell or hold securities.

The financial strength ratings of our principal operating subsidiaries and our holding company are presented below. All information is as of July 31, 2026, at which time the outlook for each of the below ratings was "Stable".

AM Best Fitch Kroll Bond Rating Agency ("KBRA")

Hamilton Re, Ltd. A A- A

Hamilton Insurance DAC A A- NR(1)

Hamilton Select A(3) NR(1) NR(1)

Hamilton Insurance Group NR(1) BBB+ Issuer Default Rating BBB+ Issuer Rating

Lloyd's Overall Market Rating(2) A+ AA- AA-

(1) Not Rated

(2) The Company's Syndicate 4000 benefits from the financial strength ratings assigned by each of AM Best, Fitch, KBRA and S&P Global ("AA-") to the Lloyd’s market.

(3) On May 12, 2026, AM Best upgraded the financial strength rating of Hamilton Select to "A" from "A-".

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Reserve for Losses and Loss Adjustment Expenses

Reserve for unpaid losses and loss adjustment expenses

The Company establishes loss reserves using actuarial models, historical insurance industry loss ratio experience and loss development patterns to estimate its ultimate liability of all losses and loss adjustment expenses incurred with respect to premiums earned on the contracts at a given point in time. Loss reserves do not represent an exact calculation of the liability. Estimates of ultimate liabilities are contingent on many future events and the eventual actual outcome of these events may be substantially different from the assumptions underlying the reserve estimates. The Company believes that the recorded reserve for losses and loss adjustment expenses represents management’s best estimate of the cost to settle the ultimate liabilities based on information available at June 30, 2026.

See Note 7, Reserve for Losses and Loss Adjustment Expenses in the accompanying unaudited condensed consolidated financial statements for the reconciliation of the gross and net reserve for losses and loss adjustment expenses and for a discussion of prior year reserve development.

Paid and unpaid losses and loss adjustment expenses recoverable

In the normal course of business, the Company seeks to reduce the potential amount of loss arising from claim events by reinsuring certain levels of risk with other reinsurers. See Summary of Critical Accounting Estimates – Ceded reinsurance and unpaid losses and loss adjustment expenses recoverable in our Form 10-K for the year ended December 31, 2025 for a detailed discussion of the Company’s risks related to ceded reinsurance agreements and the Company’s process to evaluate the financial condition of its reinsurers.

See Summary of Critical Accounting Estimates — Reserve for Losses and Loss Adjustment Expenses in our Form 10-K for the year ended December 31, 2025 for a detailed discussion of losses and loss adjustment expenses.

Recent Accounting Pronouncements

At June 30, 2026, there were no recently issued accounting pronouncements that have not yet been adopted that management expects could have a material impact on the Company’s results of operations, financial condition or liquidity. See Note 2, Summary of Significant Accounting Policies in the audited consolidated financial statements included in our Form 10-K for the year ended December 31, 2025.