The following discussion and analysis of our financial condition and results of operations should be read in conjunction with our Annual Report on Form 10-K ("Annual Report") and our Condensed Consolidated Financial Statements and related Notes included in Item 1 of Part I of this Quarterly Report on Form 10-Q ("Quarterly Report"). This discussion contains forward-looking statements based upon current expectations that involve risks and uncertainties. Please refer to the section in this Quarterly Report entitled "Cautionary Statement Regarding Forward-Looking Statements". Overview We are a market leader in providing insurance for collector cars and enthusiast vehicles, helping the automotive enthusiast community protect and enjoy their special cars for over 40 years. Through our insurance model, our wholly owned subsidiary, Hagerty Reinsurance Limited ("Hagerty Re"), reinsures collector car and enthusiast vehicle insurance risks. Hagerty Re reinsures risks predominantly from policies issued by Essentia Insurance Company ("Essentia"), a subsidiary of Markel Group Inc. ("Markel"). Markel is a related party to the Company. Refer to Note 20 — Related-Party Transactions in Item 1 of Part I of this Quarterly Report for additional information on related party transactions with Markel. We also operate as a Managing General Agent ("MGA") by underwriting, selling, and servicing collector car and enthusiast vehicle insurance policies on behalf of insurance carriers, including Hagerty Re under the Markel Fronting Arrangement. Our insurance products are complemented by our membership product, Hagerty Drivers Club ("HDC"), our renowned car events, and our media and entertainment platforms. Complementing our insurance offerings, we operate a trusted marketplace where collectors and enthusiasts can buy and sell a wide range of vehicles, from entry level enthusiast vehicles to high value collector cars. Through our marketplace, we also provide financing solutions by structuring and issuing loans secured by collector cars. Together, our integrated automotive ecosystem fosters a vibrant community where enthusiasts connect, share their passion, and access resources that enhance their ownership experience. Our vision is to be the world's most trusted and preferred brand for automotive enthusiasts to insure, buy, sell, and enjoy their special cars. Markel Fronting Arrangement On December 31, 2025, we entered into new contractual arrangements and amended the terms of our existing contractual arrangements with Markel and its affiliates. These coordinated transactions with Markel formed an arrangement that became effective January 1, 2026 (the "Markel Fronting Arrangement"). Under the Markel Fronting Arrangement: (i) we continue to issue policies through Essentia, with our underwriting authority (including pricing decisions, rate filing, insurance rating, and risk selections) and claims authority expanded to the maximum levels permitted by applicable law; (ii) we have assumed increased administrative responsibilities for the policies issued through Essentia; (iii) Hagerty Re controls 100% of the premium and assumes 100% of the risk for policies written through Essentia; and (iv) Hagerty Re pays an initial fronting fee, representing 2% of written premium, to Markel for administrative support, which incrementally decreases based on the level of written premium in each calendar year. We expect these changes to result in increased profitability and additional control, allowing for enhanced operational efficiencies. Due to the expanded underwriting and claims authority granted to us under the Markel Fronting Arrangement, we now control the Essentia book of business. While our United States ("U.S.") MGA subsidiary and Hagerty Re continue to operate in the same manner they have historically, beginning on January 1, 2026, the benefit of our MGA services with respect to the Essentia book of business is being received by Hagerty Re and not Essentia. As a result, effective in the first quarter of 2026, we are no longer recognizing commission revenue or the associated ceding commission expense for Essentia-originated policies in our Condensed Consolidated Financial Statements. However, ceding commission expense associated with Essentia policies issued in 2025 will continue to be recognized ratably over the remaining term of those policies throughout 2026. In addition, policy acquisition costs incurred by our U.S. MGA subsidiary for Essentia policies issued in 2026 are being deferred and amortized over the policy term. Although we expect the Markel Fronting Arrangement to result in increased profitability, our reported commission revenue and ceding commission expense will be lower than in prior periods, reflecting the new contractual terms governing our relationship with Markel. On December 31, 2025, in connection with the Markel Fronting Arrangement, we entered into a loss portfolio transfer agreement (the "LPT Agreement") that became effective on January 1, 2026. Pursuant to the LPT Agreement, Hagerty Re assumed 100% of the net retained liabilities for Essentia-originated policies issued prior to January 1, 2026 and received $50.5 million in cash consideration. For additional information regarding the Markel Fronting Arrangement and the LPT Agreement, refer to Note 3 — Markel Fronting Arrangement in Item 1 of Part I of this Quarterly Report. 50 TABLE OF CONTENTS Reportable Segments Due to the continued revenue growth and recent geographic expansion of the marketplace business, beginning in the fourth quarter of 2025, we updated our segment reporting to reflect two operating and reportable segments: Insurance and Marketplace. Previously, we operated as a single operating and reportable segment. We have recast prior period segment information to conform to the current presentation in this Quarterly Report. For more information regarding segment reporting, refer to Note 5 — Segment Reporting and Disaggregated Revenue in Item 1 of Part I of this Quarterly Report. Recent Developments Pending Acquisition On June 30, 2026, the Company's subsidiary, Hagerty International Holdings Limited, entered into a definitive agreement to acquire all of the issued shares of Bennetts Motorcycling Services Limited ("Bennetts"), a specialty motorcycle insurance broker in the United Kingdom ("U.K."), for a purchase price of approximately £34.0 million (approximately $43.0 million as of June 30, 2026). The transaction is subject to regulatory approval and other customary closing conditions and is expected to close during the third quarter of 2026. This acquisition builds on the international momentum Hagerty has established through Broad Arrow Auctions, which has expanded its European presence over the past year. Together, both brands can create a more integrated enthusiast platform in the U.K. – combining specialty insurance, live and digital auctions and community engagement across both motorcycles and enthusiast cars with additional cross-sell opportunities. Components of Our Results of Operations Revenue Earned premium, net Earned premium represents the earned portion of written premiums assumed under quota share reinsurance agreements with insurance carriers, net of premiums ceded to various reinsurers. Premiums assumed and ceded are recognized on a pro-rata basis over the term of the reinsured policies, which is generally 12 months. Commission and fee revenue We generate commission and fee revenue through our MGA subsidiaries, primarily from the underwriting, sale, and servicing of collector car and enthusiast vehicle insurance policies on behalf of our insurance carrier partners. Commissions are earned for both new and renewed policies. Commission and fee revenue is earned when the policy becomes effective, net of allowances for policy changes and cancellations. Effective January 1, 2026, commission revenue for Essentia-originated policies is no longer recognized in our Condensed Consolidated Statements of Operations, reflecting the new contractual terms governing our relationship with Markel, as discussed in more detail above under "Markel Fronting Arrangement". Commission and fee revenue continues to include commissions earned from our other MGA activities, including from a subsidiary of State Farm Mutual Automobile Insurance Company ("State Farm") and our insurance carrier partners in Canada and the U.K. State Farm is a related party to the Company. Refer to Note 20 — Related-Party Transactions in Item 1 of Part I of this Quarterly Report for additional information on related party transactions with State Farm. Marketplace revenue Our marketplace business generates revenue from two principal sources: (i) commission and fee-based revenue earned from the sale of collector cars and enthusiast vehicles through live auctions, time-based digital auctions, and brokered private sales; and (ii) revenue earned on the sale of collector cars and enthusiast vehicles that we have opportunistically acquired for resale. In addition, we earn finance revenue from loans made to qualified collectors and businesses secured by their collector cars. Commission and fee-based marketplace revenue is recognized on a net basis when the underlying sale is completed, which is generally upon the matching of a seller and buyer in a legally binding sale transaction. Revenue from the sale of acquired collector cars and enthusiast vehicles is recognized on a gross basis at the point in time when title and control of the vehicle is transferred to the buyer, which is generally upon collection of the full purchase price. Finance revenue is recognized over time based on the amount of the outstanding loan, the applicable interest rate on the loan, and the length of time the loan was outstanding during the period. 51 TABLE OF CONTENTS Membership and other revenue We earn subscription revenue from the sale of HDC memberships, which are bundled with our insurance policies and give members access to an array of products and services, including emergency roadside assistance, Hagerty Drivers Club Magazine, special access to automotive enthusiast events, our proprietary vehicle valuation tool, and special vehicle-related discounts. Revenue from the sale of HDC memberships is recognized ratably over the period of the membership. The membership is treated as a single performance obligation to provide access to stated Member benefits over the life of the membership, which is currently one year. Other revenue primarily includes sponsorship, admission, and advertising revenue. Other revenue is recognized when the performance obligation for the related product or service is satisfied. Net investment income Net investment income primarily consists of interest earned on our cash, cash equivalents, and fixed maturity securities, and, to a lesser extent, dividends earned from equity securities. Net investment income is recorded net of related investment management fees and expenses. Net investment gains (losses) Net investment gains (losses) represents the cumulative difference between the cost basis (or carrying value) and the net proceeds received from the sale of investments during the period, as well as the change in fair value of our equity securities between periods. Expenses Losses and loss adjustment expenses, net Losses and loss adjustment expenses represents our best estimate of the losses and associated settlement costs related to the risks we assume. Losses consist of claims paid, case reserves, and incurred but not reported ("IBNR") costs, which are recorded net of estimated recoveries from reinsurance, salvage, and subrogation. Loss adjustment expenses consist of the cost associated with processing and settling claims. Throughout the year, we record a quarterly estimate of losses and loss adjustment expenses for the current accident year using an annual loss ratio, which is based on statistical analysis performed by our internal and external actuarial teams. The annual loss ratio is reviewed regularly throughout the year and adjusted, as necessary. Management believes this approach provides a more consistent view of loss experience over the year given the seasonality of our business. Losses and loss adjustment expenses also includes the impact of reserve adjustments recorded to reflect the favorable or unfavorable development of prior accident year claims. Effective January 1, 2026, as a result of the Markel Fronting Arrangement through which we assumed control of the Essentia book of business, internal overhead costs related to claims handling and settlement for this book of business are reported within losses and loss adjustment expenses. Prior to January 1, 2026, such costs were reported within Selling, general, and administrative expenses. Policy acquisition costs, net Policy acquisition costs represents costs directly related to the successful acquisition or renewal of insurance policies where we assume risk. Prior to January 1, 2026, Policy acquisition costs included only the ceding commissions paid by Hagerty Re to insurance carriers for the risks assumed under the quota share agreements with those carriers. These commissions represented Hagerty Re's pro-rata share of the carrier's costs including (i) policy acquisition costs, which principally consisted of the commissions earned by our U.S. MGA subsidiary related to the Essentia book of business; (ii) general and administrative costs; and (iii) other costs. Effective January 1, 2026, the definition of Policy acquisition costs includes costs incurred by our U.S. MGA subsidiary for the successful acquisition or renewal of insurance policies issued under the Markel Fronting Arrangement. The policy acquisition costs associated with the Markel Fronting Arrangement primarily include (i) third-party broker expense; (ii) certain salaries, benefits, and other costs associated with underwriting, selling, issuing, and processing policies; (iii) fees paid to the fronting carrier; and (iv) premium taxes. Policy acquisition costs also includes ceding commissions paid by Hagerty Re to other insurance carriers for the risks assumed under quota share agreements. 52 TABLE OF CONTENTS Effective January 1, 2026, ceding commission expense for Essentia-originated policies is no longer recognized in our Condensed Consolidated Statements of Operations, reflecting the new contractual terms governing our relationship with Markel, as discussed in more detail above under "Markel Fronting Arrangement". Policy acquisition costs are recognized ratably over the term of the related policies, which is generally 12 months. Underwriting and other insurance expenses Underwriting and other insurance expenses consists of the operating costs incurred in connection with our risk taking activities. Effective January 1, 2026, as a result of the Markel Fronting Arrangement through which we assumed control of the Essentia book of business, Underwriting and other insurance expenses include costs incurred by our U.S. MGA subsidiary that are associated with our underwriting operations such as certain salaries and benefit costs, technology and systems costs that support the underwriting process, and expenses related to risk evaluation and pricing. Also included are general and administrative expenses attributable to the operations of our risk taking activities, including facilities costs, professional services fees, regulatory and compliance costs, and other overhead expenses. Prior to January 1, 2026, such costs were reported within Selling, general, and administrative expenses. Selling, general, and administrative expenses Selling, general, and administrative expenses primarily consists of the operating costs incurred by our non-risk taking activities, including our MGA, membership, events, and media activities, as well as our Marketplace segment. These costs primarily include salaries and benefits, sales expense, general and administrative expenses, and depreciation and amortization. Other Items Interest expense and other, net Interest expense and other primarily includes interest expense related to outstanding borrowings, primarily related to our credit facility with JPMorgan Chase Bank, N.A. ("JPM"), as well as the State Farm Term Loan (as defined in Note 14 — Debt in Item 1 of Part I of this Quarterly Report). Interest expense and other also includes the amortization of the gain from the LPT Agreement, changes in the estimated value of the liability associated with the Tax Receivable Agreement ("TRA") ("TRA Liability"), and foreign currency transaction gains and losses. Refer to Note 3 — Markel Fronting Arrangement in Item 1 of Part I of this Quarterly Report for additional information related to the LPT Agreement. Refer to Note 19 — Taxation in Item 1 of Part I of this Quarterly Report for additional information related to the TRA. Income tax (expense) benefit The Hagerty Group, LLC ("THG") is taxed as a pass-through ownership structure under provisions of the Internal Revenue Code ("IRC") and a similar section of state income tax law. As such, any taxable income or loss generated by THG is passed through to and included in the taxable income or loss of THG unit holders, including Hagerty, Inc. Hagerty, Inc. is taxed as a corporation and pays corporate federal, state, and local taxes with respect to income allocated from THG. Hagerty, Inc., Hagerty Insurance Holdings, Inc., Broad Arrow, Hagerty Radwood, Inc., and various foreign subsidiaries are treated as taxable entities and income taxes are provided where applicable. Hagerty Insurance Holdings, Inc. files a consolidated tax return with its wholly owned corporate subsidiaries Hagerty Re and Drivers Edge Insurance Company ("Drivers Edge"). Key Operating Metrics In MD&A, we discuss certain key operating metrics for the Insurance and Marketplace segments, as described below. We use these key operating metrics to evaluate our business, measure our performance, identify trends against planned initiatives, prepare financial projections, and make strategic decisions. Insurance Segment Total Written Premium represents the total amount of insurance premium written by our MGA subsidiaries on behalf of our insurance carrier partners and wholly owned insurance carrier subsidiary, Drivers Edge, during the period. Total Written Premium reflects the direct economic benefit of our policy acquisition efforts. Net Assumed Premium represents the amount of insurance premium assumed by Hagerty Re under quota share reinsurance arrangements with insurance carriers during the period, net of premiums ceded to various reinsurers. Net Assumed Premium is closely correlated with the growth of earned premium and underwriting results of Hagerty Re. 53 TABLE OF CONTENTS Hagerty Re Loss Ratio represents the ratio, expressed as a percentage, of (i) Hagerty Re's losses and loss adjustment expenses to (ii) its earned premium. Hagerty Re Loss Ratio is calculated using Hagerty Re's standalone financial statements. For the three and six months ended June 30, 2026, this excludes $3.2 million and $9.1 million, respectively, of claims handling expenses incurred by our MGA subsidiaries on behalf of Hagerty Re. Hagerty Re's standalone financial statements are prepared in accordance with accounting principles generally accepted in the United States of America ("GAAP"). This metric allows us to evaluate Hagerty Re's loss patterns on the basis of its standalone GAAP financial statements and track loss experience and identify trends that inform our pricing, reserving, and reinsurance decisions. Hagerty Re Combined Ratio represents the ratio, expressed as a percentage, of (i) Hagerty Re's losses, loss adjustment expenses, policy acquisition costs, and underwriting and other insurance expenses to (ii) its earned premium. Hagerty Re Combined Ratio is calculated using Hagerty Re's standalone GAAP financial statements. For the three and six months ended June 30, 2026, this includes $43.7 million and $55.2 million, respectively, of commissions paid to our MGA subsidiaries that are eliminated in consolidation. This metric provides a benchmark to evaluate Hagerty Re's underwriting profitability on the basis of its standalone GAAP financial statements. A combined ratio under 100% indicates underwriting income while a combined ratio exceeding 100% indicates an underwriting loss. New Business Count represents the number of new insurance policies written by our MGA subsidiaries during the period. New Business Count is an important metric to assess our financial performance because policy growth is critical to our success. While we benefit from strong policy retention through renewals, new policies more than offset those cancelled or non-renewed at expiration. New policies also often mean new relationships and an opportunity to sell additional products and services. Policies in Force ("PIF") represents the number of current and active insurance policies written by our MGA subsidiaries as of the end of the period. PIF is an important metric to assess our financial performance because policy growth drives revenue growth, increases brand awareness and market penetration, generates additional insight to improve the performance of our platform, and provides key data to assist us in strategic decision making. PIF Retention represents the percentage of expiring insurance policies written by our MGA subsidiaries that are renewed on the renewal effective date, calculated on a twelve months basis. PIF Retention is an important measurement of the number of policies retained each year, which contributes to our recurring revenue streams including commissions earned by our MGA subsidiaries, HDC membership fees, and earned premium generated by Hagerty Re. Vehicles in Force represents the number of current vehicles that are insured by policies written by our MGA subsidiaries as of the end of the period. Vehicles in Force is an important metric to assess our financial performance because insured vehicle growth drives revenue growth and increases market penetration. HDC Paid Member Count represents the number of current insurance policyholders and paid HDC subscribers (collectively, "Members") who pay an annual membership subscription as of the end of the period. HDC Paid Member Count primarily includes Members whose HDC membership is bundled with their insurance policy and paid as part of their policy premium. HDC Paid Member Count is an important metric because it helps us measure membership revenue growth and provides an opportunity to cross-sell other products and services to our Members. Marketplace Segment Aggregate Auction Sales represents the total purchase price paid by buyers, including our buyer's premium and fees, for vehicles and memorabilia purchased through Broad Arrow's live and online auctions, as well as through Hagerty Marketplace's online sale platform. Net Auction Sales represents the total purchase price paid by buyers, excluding our buyer's premium and fees, for vehicles and memorabilia purchased through Broad Arrow's live and online auctions, as well as through Hagerty Marketplace's online sale platform. Private Sales is a volume metric representing the total purchase price paid by buyers for all vehicles and memorabilia purchased through Broad Arrow's private sales business, including brokered sales and sales of our inventory. BAC Loan Portfolio Balance represents the period end loan portfolio balance of Broad Arrow Capital LLC ("BAC") recorded on our Condensed Consolidated Balance Sheets. BAC Average Loan Portfolio represents the monthly average loan portfolio balance of BAC during the period. 54 TABLE OF CONTENTS Results of Operations for the Three Months Ended June 30, 2026 and 2025 Financial Highlights The table below presents a summary of key financial measures from our Condensed Consolidated Financial Statements, which are prepared in accordance with GAAP, as well as our non-GAAP financial measures. Three months ended June 30, 2026 2025 Change GAAP Financial Measures dollars in thousands (except per share amounts) Total revenue (1) $ 354,822 $ 379,309 $ (24,487) (6.5) % Income before taxes $ 2,232 $ 53,363 $ (51,131) (95.8) % Net income $ 8,041 $ 47,202 $ (39,161) (83.0) % Net income (loss) attributable to Class A Common Stockholders $ (1,668) $ 9,098 $ (10,766) (118.3) % Basic earnings (loss) per share ("EPS") $ (0.02) $ 0.09 $ (0.11) (122.2) % Diluted EPS $ (0.02) $ 0.09 $ (0.11) (122.2) % Non-GAAP Financial Measures Adjusted EBITDA (2) $ 74,505 $ 72,645 $ 1,860 2.6 % Adjusted Net Income (Loss) (2) $ (6,188) $ 43,450 $ (49,638) (114.2) % Adjusted Diluted EPS (2) $ (0.02) $ 0.12 $ (0.14) (116.7) % (1) Refer to Note 2 — Summary of Significant Accounting Policies in Item 1 of Part I of this Quarterly Report for a reconciliation of prior year revenue to current year presentation. (2) Adjusted EBITDA, Adjusted Net Income (Loss), and Adjusted Diluted EPS are non-GAAP financial measures. Please see the section titled "Non-GAAP Financial Measures" below for a description of these non-GAAP financial measures and a reconciliation to the most comparable GAAP measure, as well as a reconciliation of prior year Adjusted EBITDA to the current year presentation. For the three months ended June 30, 2026, we reported Net income of $8.0 million, representing a $39.2 million, or 83.0%, decrease compared to the prior year, and Adjusted EBITDA of $74.5 million, representing a $1.9 million, or 2.6%, increase compared to the prior year. In our Insurance segment, Income before taxes for the three months ended June 30, 2026 was $2.8 million, representing a $58.0 million decrease from the prior year. This decrease is due to the transition of our business under the Markel Fronting Arrangement, which resulted in lower Commission and fee revenue and the recognition of non-cash costs to amortize the remaining deferred ceding commissions for Essentia policies written in 2025. These factors are partially offset by a $74.2 million, or 41.7%, increase in Earned premium, net, reflecting the increase to our quota share percentage from 80% to 100% under the Markel Fronting Arrangement, as well as the continued growth of that book of business. In our Marketplace segment, Income before taxes for the three months ended June 30, 2026 was $1.1 million, compared to a loss of $2.0 million in the prior period. The improved Marketplace segment results are principally due to increased auction revenue, which was driven by an 80.3% increase in Net Auction Sales from the 2026 Concorso d’Eleganza Villa d’Este Auction, reflecting further growth of Broad Arrow's international business. 55 TABLE OF CONTENTS Insurance Segment The following table summarizes Insurance segment results of operations for the three months ended June 30, 2026 and 2025, and the dollar and percentage changes between the two periods: Three months ended June 30, 2026 2025 $ Change % Change Segment Results: dollars in thousands REVENUES: Earned premium, net $ 251,956 $ 177,785 $ 74,171 41.7 % Commission and fee revenue 23,665 143,287 (119,622) (83.5) % Membership and other revenue 21,361 20,741 620 3.0 % Net investment income 10,731 9,287 1,444 15.5 % Net investment gains 7,179 1,194 5,985 N/M Total revenue 314,892 352,294 (37,402) (10.6) % EXPENSES: Losses and loss adjustment expenses, net 110,709 75,213 35,496 47.2 % Policy acquisition costs, net 83,641 82,938 703 0.8 % Underwriting and other insurance expenses 62,947 1,222 61,725 N/M Selling, general, and administrative expenses 55,931 131,634 (75,703) (57.5) % Interest expense and other, net (1,103) 528 (1,631) N/M Total expenses 312,125 291,535 20,590 7.1 % INCOME BEFORE TAXES $ 2,767 $ 60,759 $ (57,992) (95.4) % Operational Metrics: Total Written Premium $ 424,502 $ 355,985 $ 68,517 19.2 % Net Assumed Premium $ 333,152 $ 236,603 $ 96,549 40.8 % Hagerty Re Loss Ratio 42.7 % 42.3 % 0.4 % N/M Hagerty Re Combined Ratio 89.6 % 89.6 % — % N/M New Business Count — Insurance 166,951 87,872 79,079 90.0 % June 30, 2026 2025 Change Operational Metrics: Policies in Force 1,855,649 1,559,798 295,851 19.0 % Policies in Force Retention 88.2 % 88.7 % (0.5) % N/M Vehicles in Force 3,031,566 2,664,611 366,955 13.8 % HDC Paid Member Count 961,929 907,963 53,966 5.9 % N/M = Not meaningful As discussed in greater detail above under "Markel Fronting Arrangement", due to the expanded underwriting and claims authority granted to us under the Markel Fronting Arrangement, we now control the Essentia book of business. While our U.S. MGA subsidiary and Hagerty Re continue to operate in the same manner they have historically, beginning on January 1, 2026, the benefit of our MGA services is being received by Hagerty Re and not Essentia. As a result, effective in the first quarter of 2026, we are no longer recognizing commission revenue or the associated ceding commission expense for Essentia-originated policies in our Condensed Consolidated Financial Statements. However, ceding commission expense associated with Essentia policies issued in 2025 will continue to be recognized ratably over the remaining term of those policies throughout 2026. In addition, policy acquisition costs incurred by our U.S. MGA subsidiary for Essentia policies issued in 2026 are being deferred and amortized over the policy term. Accordingly, our entry into the Markel Fronting Arrangement has reduced the period‑to‑period comparability of our Condensed Consolidated Financial Statements. 56 TABLE OF CONTENTS The following table provides a reconciliation of the standalone results of operations for our Hagerty Re and MGA+ reporting units for the three months ended June 30, 2026, which reflect the continuing operations of those businesses, to total insurance segment results of operations included in our Condensed Consolidated Statements of Operations. This table is presented solely to improve the year-over-year comparability of our financial statements and should not be viewed on a standalone basis. It should be read together with our Condensed Consolidated Statements of Operations and the accompanying notes. Three months ended June 30, 2026 Hagerty Re:Essentia Policy Year 2025 (a) Hagerty Re:Essentia Policy Year 2026 & Other Carriers (b) Hagerty Re Total MGA+ (c) Consolidation Entries Insurance Segment REVENUES: in thousands Earned premium, net $ 157,365 $ 94,591 $ 251,956 $ — $ — $ 251,956 Commission and fee revenue — 167,213 (143,548) (e) 23,665 Membership and other revenue — 21,361 — 21,361 Net investment income 9,694 1,037 — 10,731 Net investment gains 7,179 — — 7,179 Total revenue 268,829 189,611 (143,548) 314,892 EXPENSES: Losses and loss adjustment expenses, net 107,522 3,187 (d) — 110,709 Policy acquisition costs, net: Ceding commission expense 71,614 38,959 110,573 — (43,647) (e) 66,926 Other policy acquisition costs 4,560 — 12,155 (f) 16,715 Underwriting and other insurance expenses 2,990 92,037 (d) (32,080) (f) 62,947 Selling, general, and administrative expenses — 55,931 — 55,931 Interest expense and other, net (1,118) 15 — (1,103) Total expenses 224,527 151,170 (63,572) 312,125 INCOME BEFORE TAXES $ 44,302 $ 38,441 $ (79,976) $ 2,767 (g) (a) Represents Hagerty Re's earned premium and associated policy acquisition costs related to Essentia policies issued in 2025. (b) Represents Hagerty Re's earned premium and associated policy acquisition costs related to Essentia policies issued in 2026 and through other carriers. (c) The MGA+ reporting unit includes our MGA operations, as well as our membership, events, and media activities. (d) Our MGA subsidiaries incur costs to fulfill certain underwriting and claims handling functions on behalf of Hagerty Re, for which they are compensated through an intercompany commission paid by Hagerty Re. These costs are reflected within the standalone results of our MGA+ reporting unit within "Losses and loss adjustment expenses, net" and "Underwriting and other insurance expenses". (e) These consolidation entries are made to eliminate intercompany commission revenue and ceding commission expense between the Hagerty Re and MGA+ reporting units. (f) These consolidation entries are made to defer $32.1 million in policy acquisition costs incurred by the MGA+ reporting unit in their standalone results of operations, which are then amortized over the underlying policy term in our Condensed Consolidated Statements of Operations. For the three months ended June 30, 2026, the amortization of such deferred policy acquisition costs totaled $12.2 million. (g) Refer to Note 5 — Segment Reporting and Disaggregated Revenue in Item 1 of Part I of this Quarterly Report for a reconciliation of Insurance segment Income before taxes to consolidated Income before taxes. Earned premium, net Earned premium, net was $252.0 million for the three months ended June 30, 2026, an increase of $74.2 million, or 41.7%, compared to 2025. This increase is primarily driven by our entry into the Markel Fronting Arrangement, which became effective January 1, 2026 and increased Hagerty Re's U.S. quota share from approximately 80% to 100%, including for in-force policies written in 2025. To a lesser extent, the increase is driven by growth in subject premiums written through our MGA subsidiaries. 57 TABLE OF CONTENTS The following tables present premiums assumed and earned, as well as the related quota share percentages for the three months ended June 30, 2026 and 2025: Three months ended June 30, 2026 U.S. Canada U.K. (1) Total in thousands (except percentages) Subject premium (2) $ 346,295 $ 30,046 $ — $ 376,341 Quota share percentage 100.0 % 50.0 % — % 96.0 % Assumed premium 346,295 15,023 — 361,318 Reinsurance premiums ceded (28,166) Net assumed premium 333,152 Change in unearned premiums (90,642) Change in deferred reinsurance premiums 9,446 Earned premium, net $ 251,956 (1) In 2026, we did not reinsure classic auto risks produced by our U.K. MGA subsidiary, and the prior book of business is in run-off. (2) Represents the portion of total written premium subject to reinsurance agreements. Three months ended June 30, 2025 U.S. Canada U.K. (1) Total in thousands (except percentages) Subject premium (2) $ 290,188 $ 27,014 $ (43) $ 317,159 Quota share percentage 81.0 % 50.0 % 80.0 % 78.1 % Assumed premium 234,339 13,507 (34) 247,812 Reinsurance premiums ceded (11,209) Net assumed premium 236,603 Change in unearned premiums (57,836) Change in deferred reinsurance premiums (982) Earned premium, net $ 177,785 (1) In 2025, we did not reinsure classic auto risks produced by our U.K. MGA subsidiary, and the prior book of business is in run-off. (2) Represents the portion of total written premium subject to reinsurance agreements. Losses and loss adjustment expenses, net Losses and loss adjustment expenses, net were $110.7 million for the three months ended June 30, 2026, an increase of $35.5 million, or 47.2%, compared to 2025. This increase is primarily the result of the Markel Fronting Arrangement, which increased Hagerty Re's U.S. quota share from approximately 80% to 100% as of January 1, 2026 for all in-force policies. To a lesser extent, the increase is driven by continued growth of subject premiums written through our MGA subsidiaries. For the three months ended June 30, 2026, the Hagerty Re Loss Ratio was 42.7%, an increase of 0.4% from 2025, when the Hagerty Re Loss Ratio was 42.3%. Refer to the section "Losses and loss adjustment expenses, net" under the Results of Operations for the six months ended June 30, 2026 for further discussion. Policy acquisition costs, net Policy acquisition costs, net were $83.6 million for the three months ended June 30, 2026, an increase of $0.7 million, or 0.8%, compared to 2025. Policy acquisition costs, net remained relatively flat despite growth in earned premium, reflecting a change in the composition of expenses following the transition of our business under the Markel Fronting Arrangement. Refer to the discussion of Policy acquisition costs, net within the section "Components of Our Results of Operations" above for additional details. 58 TABLE OF CONTENTS Underwriting and other insurance expenses Underwriting and other insurance expenses were $62.9 million for the three months ended June 30, 2026, an increase of $61.7 million compared to 2025. This increase is primarily due to the transition of our business under the Markel Fronting Arrangement, which required a different classification of certain costs in our Condensed Consolidated Statements of Operations. Beginning in 2026, because we now control the Essentia book of business, certain operating costs incurred by our U.S. MGA subsidiary in support of our risk taking activities are classified within "Underwriting and other insurance expenses". In 2025, prior to assuming control of the Essentia book of business, these costs were categorized within "Selling, general, and administrative expenses". Net investment income and Net investment gains The following table presents the components of Net investment income and Net investment gains related to the Insurance segment for the three months ended June 30, 2026 and 2025: Three months ended June 30, 2026 2025 $ Change % Change in thousands (except percentages) Interest income $ 10,761 $ 9,378 $ 1,383 14.7% Dividend income 157 39 118 N/M Investment management fees and expenses (187) (130) (57) (43.8)% Net investment income 10,731 9,287 1,444 15.5% Net investment gains 7,179 1,194 5,985 N/M Total $ 17,910 $ 10,481 $ 7,429 70.9% N/M = Not meaningful The increase in Net investment income is due to an increase in the size of our fixed maturity securities portfolio when compared to the prior year. The increase in Net investment gains is primarily driven by unrealized gains on equity securities in the period. Other revenues Commission and fee revenue Commission and fee revenue was $23.7 million for the three months ended June 30, 2026, a decrease of $119.6 million, or 83.5%, compared to 2025. This decrease is primarily due to the transition of our business under the Markel Fronting Arrangement. Due to the expanded underwriting and claims authority granted to us under the Markel Fronting Arrangement, we now control the Essentia book of business and, as a result, beginning on January 1, 2026, the benefit of our MGA services is being received by Hagerty Re and not Essentia. As a result, effective in the first quarter of 2026, we no longer recognize commission revenue for Essentia-originated policies in our Condensed Consolidated Financial Statements. This decrease is partially offset by an increase of $5.0 million related to policies written under the State Farm Master Alliance Agreement. Membership and other revenue Membership and other revenue was $21.4 million for the three months ended June 30, 2026, an increase of $0.6 million, or 3.0%, compared to 2025. This increase is primarily due to a $1.5 million, or 10.1%, increase in revenue attributable to new insurance policies issued with a bundled HDC membership, partially offset by a decrease of $0.7 million in advertising revenue. Other expenses Selling, general, and administrative expenses Selling, general, and administrative expenses were $55.9 million for the three months ended June 30, 2026, a decrease of $75.7 million, or 57.5%, compared to 2025. This decrease is primarily due to the transition of our business under the Markel Fronting Arrangement, which required a different classification of certain costs in our Condensed Consolidated Statements of Operations. Beginning in 2026, because we now control the Essentia book of business, certain costs incurred by our U.S. MGA subsidiary in support of our risk taking activities, are classified within "Losses and loss adjustment expenses, net", "Policy acquisition costs, net", and "Underwriting and other insurance expenses". In 2025, prior to assuming control of the Essentia book of business, these costs were categorized within "Selling, general, and administrative expenses". 59 TABLE OF CONTENTS Marketplace Segment The following table summarizes Marketplace segment results of operations for the three months ended June 30, 2026 and 2025, and the dollar and percentage changes between the two periods: Three months ended June 30, 2026 2025 $ Change % Change Segment Results: in thousands (except percentages) REVENUES: Marketplace revenue $ 39,658 $ 26,886 $ 12,772 47.5 % Net investment income 272 129 143 110.9 % Total revenue 39,930 27,015 12,915 47.8 % EXPENSES: Selling, general, and administrative expenses (1) 38,984 29,165 9,819 33.7 % Interest expense and other, net (106) (144) 38 26.4 % Total expenses 38,878 29,021 9,857 34.0 % INCOME (LOSS) BEFORE TAXES $ 1,052 $ (2,006) $ 3,058 152.4 % Operational Metrics: Aggregate Auction Sales $ 104,446 $ 49,408 $ 55,038 111.4 % Net Auction Sales $ 94,374 $ 44,837 $ 49,537 110.5 % Private Sales (2) $ 44,136 $ 114,776 $ (70,640) (61.5) % BAC Average Loan Portfolio $ 146,363 $ 81,233 $ 65,130 80.2 % June 30, 2026 2025 $ Change % Change Operational Metrics: in thousands (except percentages) BAC Loan Portfolio Balance $ 146,550 $ 84,515 $ 62,035 73.4 % (1) Selling expenses include direct costs associated with the sale of vehicles and memorabilia through auctions and private sales, including the purchase price and associated direct costs of inventory when Broad Arrow opportunistically purchases vehicles to be sold through auctions or private sales, as well as interest expense and borrowing costs associated with the BAC Credit Facility. (2) Private Sales is a gross transaction-volume metric that includes both brokered private sales, for which we recognize revenue on a net commission basis, and sales of our inventory, for which we recognize revenue on a gross basis. The decrease in Private Sales is primarily attributable to lower brokered private sale volume compared to the prior year, which included the private sale of a sizable single-owner collection. Because brokered private sales are recognized net, this decline did not have a proportionate impact on Marketplace revenue or income before taxes. Income before taxes for the Marketplace segment was $1.1 million for the three months ended June 30, 2026, an increase of $3.1 million compared to 2025. The improved Marketplace segment results are principally due to increased auction revenue, which was driven by an 80.3% increase in Net Auction Sales attributable to the 2026 Concorso d’Eleganza Villa d’Este Auction. To a much lesser extent, the increase in Marketplace segment results is driven by an increase in finance revenue due to an 80.2% increase in the BAC Average Loan Portfolio Balance during the period, which was enabled by the upsizing of the BAC Credit Facility in the fourth quarter of 2025. Interest expense and other, net Three months ended June 30, 2026 2025 $ Change % Change in thousands (except percentages) Amortization of deferred LPT gain $ (1,632) $ — $ (1,632) (100.0) % Interest expense 1,760 1,999 (239) (12.0) % Change in TRA Liability — 3,078 (3,078) (100.0) % Other (income) expense (100) (131) 31 23.7 % Interest expense and other, net $ 28 $ 4,946 $ (4,918) (99.4) % 60 TABLE OF CONTENTS Amortization of deferred LPT gain Amortization of the deferred gain associated with the LPT Agreement was $1.6 million for the three months ended June 30, 2026, with no comparable amount in the prior year period. The LPT Agreement became effective on January 1, 2026 in connection with the Markel Fronting Arrangement, and the associated deferred gain is being recognized within "Interest expense and other, net" over the expected period of future claim payments. Refer to Note 3 — Markel Fronting Arrangement in Item 1 of Part I of this Quarterly Report for additional information. Interest expense During the three months ended June 30, 2026, Interest expense decreased $0.2 million compared to 2025. This decrease is the result of a lower interest rate incurred on borrowings under the JPM Credit Facility for the three months ended June 30, 2026, when compared to the prior year. Change in TRA Liability During the three months ended June 30, 2025, we recorded $3.1 million of expense due to a change in the value of the TRA Liability. There was no such expense recorded during the three months ended June 30, 2026. The expense related to the remeasurement of the TRA Liability is recorded within "Interest expense and other, net" in the Condensed Consolidated Statements of Operations. Refer to Note 19 — Taxation in Item 1 of Part I of this Quarterly Report for additional information. Income tax (expense) benefit We are the sole managing member of THG, and as a result, consolidate its financial results. THG is treated as a partnership for U.S. federal and most applicable state and local income tax purposes. As a partnership, THG is not subject to U.S. federal and certain state and local income taxes. Any taxable income or loss generated by THG is passed through and included in the taxable income or loss of its members, including Hagerty, Inc., on a pro rata basis. Hagerty, Inc. is subject to U.S. federal, state and local income taxes with respect to its allocable share of any taxable income or loss of THG, as well as any of its stand-alone income or loss. In addition, Hagerty Insurance Holdings, Inc., Broad Arrow, Hagerty Radwood, Inc., and various foreign subsidiaries are treated as taxable entities. Hagerty Insurance Holdings, Inc. files a consolidated tax return with its wholly owned corporate subsidiaries Hagerty Re and Drivers Edge. For the three months ended June 30, 2026, we recorded an income tax benefit of $5.8 million, resulting in an effective tax rate of (260.3)%, compared to income tax expense of $6.2 million for the three months ended June 30, 2025, resulting in an effective tax rate of 11.5%. The change in income tax benefit (expense) period over period is driven by non-reversing temporary differences between taxable income and pre-tax book income related to the Markel Fronting Arrangement, partially offset by higher earnings in Hagerty Re and an increase in Hagerty, Inc.'s allocable share of income from THG. 61 TABLE OF CONTENTS Results of Operations for the Six Months Ended June 30, 2026 and 2025 Financial Highlights Six months ended June 30, 2026 2025 Change GAAP Financial Measures dollars in thousands (except per share amounts) Total revenue (1) $ 666,652 $ 707,645 $ (40,993) (5.8) % Income (loss) before taxes $ (18,705) $ 86,145 $ (104,850) (121.7) % Net income (loss) $ (4,704) $ 74,495 $ (79,199) (106.3) % Net income (loss) attributable to Class A Common Stockholders $ (8,189) $ 15,594 $ (23,783) (152.5) % Basic EPS $ (0.08) $ 0.16 $ (0.24) (150.0) % Diluted EPS $ (0.08) $ 0.16 $ (0.24) (150.0) % Non-GAAP Financial Measures Adjusted EBITDA (2) $ 159,690 $ 120,796 $ 38,894 32.2 % Adjusted Net Income (Loss) (2) $ (19,332) $ 68,802 $ (88,134) (128.1) % Adjusted Diluted EPS (2) $ (0.05) $ 0.19 $ (0.24) (126.3) % (1) Refer to Note 2 — Summary of Significant Accounting Policies in Item 1 of Part I of this Quarterly Report for a reconciliation of prior year revenue to current year presentation. (2) Adjusted EBITDA, Adjusted Net Income (Loss), and Adjusted Diluted EPS are non-GAAP financial measures. Please see the section titled "Non-GAAP Financial Measures" below for a description of these non-GAAP financial measures and a reconciliation to the most comparable GAAP measure, as well as a reconciliation of prior year Adjusted EBITDA to the current year presentation. For the six months ended June 30, 2026, we reported a Net loss of $4.7 million, representing a $79.2 million decrease compared to the prior year, and Adjusted EBITDA of $159.7 million, representing a $38.9 million, or 32.2%, increase compared to the prior year. In our Insurance segment, Loss before taxes for the six months ended June 30, 2026 was $17.6 million, representing a $111.2 million decrease from the prior year. The loss for the current period is due to the transition of our business under the Markel Fronting Arrangement, which resulted in a decrease in Commission and fee revenue and the recognition of non-cash costs to amortize the remaining deferred ceding commissions for Essentia policies written in 2025. These factors are partially offset by a $144.5 million, or 41.6%, increase in Earned premium, net, reflecting the increase to our quota share percentage from 80% to 100% under the Markel Fronting Arrangement, as well as the continued growth of that book of business. In our Marketplace segment, Income before taxes for the six months ended June 30, 2026 was $1.8 million, compared to a loss of $0.5 million in the prior period. The improved Marketplace segment results are principally due to increased auction revenue, which was driven by increases in Net Auction Sales of 90.0% and 80.3% from The Amelia and the Concorso d’Eleganza Villa d’Este auctions, respectively. To a much lesser extent, the increase in auction revenue is also due to the inaugural Global Icons online auction during the Salon Retromobile week in Paris and the inaugural Spring Global Icons auction. 62 TABLE OF CONTENTS Insurance Segment The following table summarizes Insurance segment results of operations for the six months ended June 30, 2026 and 2025, and the dollar and percentage changes between the two periods: Six months ended June 30, 2026 2025 $ Change % Change Segment Results: dollars in thousands REVENUES: Earned premium, net $ 491,598 $ 347,140 $ 144,458 41.6 % Commission and fee revenue 40,100 243,574 (203,474) (83.5) % Membership and other revenue 43,488 41,606 1,882 4.5 % Net investment income 20,745 18,170 2,575 14.2 % Net investment gains 4,890 879 4,011 N/M Total revenue 600,821 651,369 (50,548) (7.8) % EXPENSES: Losses and loss adjustment expenses, net 208,628 146,343 62,285 42.6 % Policy acquisition costs, net 185,563 160,271 25,292 15.8 % Underwriting and other insurance expenses 122,535 2,579 119,956 N/M Selling, general, and administrative expenses 102,797 247,575 (144,778) (58.5) % Interest expense and other, net (1,119) 940 (2,059) N/M Total expenses 618,404 557,708 60,696 10.9 % INCOME (LOSS) BEFORE TAXES $ (17,583) $ 93,661 $ (111,244) (118.8) % Operational Metrics: Total Written Premium $ 713,448 $ 600,312 $ 113,136 18.8 % Net Assumed Premium $ 650,498 $ 392,254 $ 258,244 65.8 % Hagerty Re Loss Ratio 40.6 % 42.2 % (1.6) % N/M Hagerty Re Combined Ratio 88.1 % 89.1 % (1.0) % N/M New Business Count — Insurance 278,847 143,181 135,666 94.8 % June 30, 2026 2025 Change Operational Metrics: Policies in Force 1,855,649 1,559,798 295,851 19.0 % Policies in Force Retention 88.2 % 88.7 % (0.5) % N/M Vehicles in Force 3,031,566 2,664,611 366,955 13.8 % HDC Paid Member Count 961,929 907,963 53,966 5.9 % N/M = Not meaningful As discussed in greater detail above under "Markel Fronting Arrangement", due to the expanded underwriting and claims authority granted to us under the Markel Fronting Arrangement, we now control the Essentia book of business. While our U.S. MGA subsidiary and Hagerty Re continue to operate in the same manner they have historically, beginning on January 1, 2026, the benefit of our MGA services is being received by Hagerty Re and not Essentia. As a result, effective in the first quarter of 2026, we are no longer recognizing commission revenue or the associated ceding commission expense for Essentia-originated policies in our Condensed Consolidated Financial Statements. However, ceding commission expense associated with Essentia policies issued in 2025 will continue to be recognized ratably over the remaining term of those policies throughout 2026. In addition, policy acquisition costs incurred by our U.S. MGA subsidiary for Essentia policies issued in 2026 are being deferred and amortized over the policy term. Accordingly, our entry into the Markel Fronting Arrangement has reduced the period‑to‑period comparability of our Condensed Consolidated Financial Statements. 63 TABLE OF CONTENTS The following table provides a reconciliation of the standalone results of operations for our Hagerty Re and MGA+ reporting units for the six months ended June 30, 2026, which reflect the continuing operations of those businesses, to our Condensed Consolidated Statements of Operations. This table is presented solely to improve the year-over-year comparability of our financial statements and should not be viewed on a standalone basis. It should be read together with our Condensed Consolidated Statements of Operations and the accompanying notes. Six months ended June 30, 2026 Hagerty Re:Essentia Policy Year 2025 (a) Hagerty Re:Essentia Policy Year 2026 & Other Carriers (b) Hagerty Re Total MGA+ (c) Consolidation Entries Insurance Segment REVENUES: in thousands Earned premium, net $ 375,638 $ 115,960 $ 491,598 $ — $ — $ 491,598 Commission and fee revenue — 287,449 (247,349) (e) 40,100 Membership and other revenue — 43,488 — 43,488 Net investment income 18,926 1,819 — 20,745 Net investment gains 4,890 — — 4,890 Total revenue 515,414 332,756 (247,349) 600,821 EXPENSES: Losses and loss adjustment expenses, net 199,487 9,141 (d) — 208,628 Policy acquisition costs, net: Ceding commission expense 170,971 47,700 218,671 — (55,188) (e) 163,483 Other policy acquisition costs 5,787 — 16,293 (f) 22,080 Underwriting and other insurance expenses 9,040 170,740 (d) (57,245) (f) 122,535 Selling, general, and administrative expenses — 102,797 — 102,797 Interest expense and other, net (1,911) 792 — (1,119) Total expenses 431,074 283,470 (96,140) 618,404 INCOME (LOSS) BEFORE TAXES $ 84,340 $ 49,286 $ (151,209) $ (17,583) (g) (a) Represents Hagerty Re's earned premium and associated policy acquisition costs related to Essentia policies issued in 2025. (b) Represents Hagerty Re's earned premium and associated policy acquisition costs related to Essentia policies issued in 2026 and through other carriers. (c) The MGA+ reporting unit includes our MGA operations, as well as our membership, events, and media activities. (d) Our MGA subsidiaries incur costs to fulfill certain underwriting and claims handling functions on behalf of Hagerty Re, for which they are compensated through an intercompany commission paid by Hagerty Re. These costs are reflected within the standalone results of our MGA+ reporting unit within "Losses and loss adjustment expenses, net" and "Underwriting and other insurance expenses". (e) These consolidation entries are made to eliminate intercompany commission revenue and ceding commission expense between the Hagerty Re and MGA+ reporting units. (f) These consolidation entries are made to defer $57.2 million in policy acquisition costs incurred by the MGA+ reporting unit in their standalone results of operations, which are then amortized over the underlying policy term in our Condensed Consolidated Statements of Operations. For the six months ended June 30, 2026, the amortization of such deferred policy acquisition costs totaled $16.3 million. (g) Refer to Note 5 — Segment Reporting and Disaggregated Revenue in Item 1 of Part I of this Quarterly Report for a reconciliation of Insurance segment Income (loss) before taxes to consolidated Income (loss) before taxes. Earned premium, net Earned premium, net was $491.6 million for the six months ended June 30, 2026, an increase of $144.5 million, or 41.6%, compared to 2025. This increase is primarily driven by our entry into the Markel Fronting Arrangement, which became effective January 1, 2026 and increased Hagerty Re's U.S. quota share from approximately 80% to 100%, including for in-force policies written in 2025. To a lesser extent, the increase is driven by growth in subject premiums written through our MGA subsidiaries. 64 TABLE OF CONTENTS The following tables present premiums assumed and earned, as well as the related quota share percentages for the six months ended June 30, 2026 and 2025: Six months ended June 30, 2026 U.S. Canada U.K. (1) Total in thousands (except percentages) Subject premium (2) (3) $ 692,032 $ 39,041 $ — $ 731,073 Quota share percentage 100.0 % 50.0 % — % 97.3 % Assumed premium (3) 692,032 19,521 — 711,553 Reinsurance premiums ceded (61,055) Net assumed premium 650,498 Change in unearned premiums (186,806) Change in deferred reinsurance premiums 27,906 Earned premium, net $ 491,598 (1) In 2026, we did not reinsure classic auto risks produced by our U.K. MGA subsidiary, and the prior book of business is in run-off. (2) Represents the portion of total written premium subject to reinsurance agreements. (3) Includes $92.6 million of premium assumed on January 1, 2026 in connection with our entry into the Markel Fronting Arrangement, representing the incremental 20% risk assumed for policies issued in 2025. Six months ended June 30, 2025 U.S. Canada U.K. (1) Total in thousands (except percentages) Subject premium (2) $ 502,056 $ 34,526 $ (37) $ 536,545 Quota share percentage 81.0 % 50.0 % 80.0 % 78.9 % Assumed premium 406,089 17,263 (29) 423,323 Reinsurance premiums ceded (31,069) Net assumed premium 392,254 Change in unearned premiums (52,414) Change in deferred reinsurance premiums 7,300 Earned premium, net $ 347,140 (1) In 2025, we did not reinsure classic auto risks produced by our U.K. MGA subsidiary, and the prior book of business is in run-off. (2) Represents the portion of total written premium subject to reinsurance agreements. Losses and loss adjustment expenses, net Losses and loss adjustment expenses, net were $208.6 million for the six months ended June 30, 2026, an increase of $62.3 million, or 42.6%, compared to 2025. This increase is primarily the result of the Markel Fronting Arrangement, which increased Hagerty Re's U.S. quota share from approximately 80% to 100% as of January 1, 2026 for all in-force policies. To a lesser extent, the increase is driven by continued growth of subject premiums written through our MGA subsidiaries. During the six months ended June 30, 2026, loss experience developed favorably resulting in a $6.1 million reserve reduction, primarily driven by the continued emergence of lower physical damage losses for the 2025 accident year. During the six months ended June 30, 2025, losses and loss adjustment expenses included $10.3 million of pre-tax losses related to the Southern California Wildfires. For the six months ended June 30, 2026, the Hagerty Re Loss Ratio was 40.6%, a decrease of 1.6% from 2025, when the Hagerty Re Loss Ratio was 42.2%. 65 TABLE OF CONTENTS Policy acquisition costs, net Policy acquisition costs, net were $185.6 million for the six months ended June 30, 2026, an increase of $25.3 million, or 15.8%, compared to 2025. This increase is due to the transition of our business under the Markel Fronting Arrangement, which resulted in incremental ceding commission expense for in-force policies written in 2025 and assumed at 100% on January 1, 2026. Also contributing to the increase in policy acquisition costs over the prior year is the continued growth of subject premiums and resulting increase in earned premium. This increase was partially offset by a decrease in Policy acquisition costs as a result of a change in the composition of expenses following our entry into the Markel Fronting Arrangement. In the prior year, Policy acquisition costs predominantly included the ceding commissions paid by Hagerty Re to Essentia for the risks assumed under the prior quota share agreement. Effective January 1, 2026, because we now control the Essentia book of business, Policy acquisition costs, net include costs incurred by our U.S. MGA subsidiary for the successful acquisition or renewal of insurance policies issued under the Markel Fronting Arrangement. These policy acquisition costs are deferred and recognized ratably over the term of the related policies, which is generally 12 months. Costs that are not directly attributable to the successful acquisition of policies where we assume risk are expensed as incurred within "Underwriting and other insurance expenses". Underwriting and other insurance expenses Underwriting and other insurance expenses were $122.5 million for the six months ended June 30, 2026, an increase of $120.0 million compared to 2025. This increase is primarily due to the transition of our business under the Markel Fronting Arrangement, which required a different classification of certain costs in our Condensed Consolidated Statements of Operations. Beginning in 2026, because we now control the Essentia book of business, certain operating costs incurred by our U.S. MGA subsidiary in support of our risk taking activities are classified within "Underwriting and other insurance expenses". In 2025, prior to assuming control of the Essentia book of business, these costs were categorized within "Selling, general, and administrative expenses". Net investment income and Net investment gains The following table presents the components of Net investment income and Net investment gains related to the Insurance segment for the six months ended June 30, 2026 and 2025: Six months ended June 30, 2026 2025 $ Change % Change in thousands (except percentages) Interest income $ 20,745 $ 18,348 $ 2,397 13.1% Dividend income 364 79 285 N/M Investment management fees and expenses (364) (257) (107) (41.6)% Net investment income 20,745 18,170 2,575 14.2% Net investment gains 4,890 879 4,011 N/M Total $ 25,635 $ 19,049 $ 6,586 34.6% N/M = Not meaningful The increase in Net investment income is due to an increase in the size of our fixed maturity securities portfolio when compared to the prior year. The increase in Net investment gains is primarily driven by unrealized gains on equity securities in the period. Other revenues Commission and fee revenue Commission and fee revenue was $40.1 million for the six months ended June 30, 2026, a decrease of $203.5 million, or 83.5%, compared to 2025. This decrease is primarily due to the transition of our business under the Markel Fronting Arrangement. Due to the expanded underwriting and claims authority granted to us under the Markel Fronting Arrangement, we now control the Essentia book of business and, as a result, beginning on January 1, 2026, the benefit of our MGA services is being received by Hagerty Re and not Essentia. As a result, effective in the first quarter of 2026, we no longer recognize commission revenue for Essentia-originated policies in our Condensed Consolidated Financial Statements. This decrease is partially offset by an increase of $10.5 million related to policies written under the State Farm Master Alliance Agreement. 66 TABLE OF CONTENTS Membership and other revenue Membership and other revenue was $43.5 million for the six months ended June 30, 2026, an increase of $1.9 million, or 4.5%, compared to 2025. This increase is primarily due to a $2.9 million, or 10.2%, increase in revenue attributable to new insurance policies issued with a bundled HDC membership. Other expenses Selling, general, and administrative expenses Selling, general, and administrative expenses were $102.8 million for the six months ended June 30, 2026, a decrease of $144.8 million, or 58.5%, compared to 2025. This decrease is primarily due to the transition of our business under the Markel Fronting Arrangement, which required a different classification of certain costs in our Condensed Consolidated Statements of Operations. Beginning in 2026, because we now control the Essentia book of business, certain costs incurred by our U.S. MGA subsidiary in support of our risk taking activities, are classified within "Losses and loss adjustment expenses, net", "Policy acquisition costs, net", and "Underwriting and other insurance expenses". In 2025, prior to assuming control of the Essentia book of business, these costs were categorized within "Selling, general, and administrative expenses". Marketplace Segment The following table summarizes Marketplace segment results of operations for the six months ended June 30, 2026 and 2025, and the dollar and percentage changes between the two periods: Six months ended June 30, 2026 2025 $ Change % Change Segment Results: in thousands (except percentages) REVENUES: Marketplace revenue $ 65,310 $ 55,972 $ 9,338 16.7 % Net investment income 521 304 217 71.4 % Total revenue 65,831 56,276 9,555 17.0 % EXPENSES: Selling, general, and administrative expenses (1) 64,256 57,004 7,252 12.7 % Interest expense and other, net (263) (260) (3) (1.2) % Total expenses 63,993 56,744 7,249 12.8 % INCOME (LOSS) BEFORE TAXES $ 1,838 $ (468) $ 2,306 N/M Operational Metrics: Aggregate Auction Sales $ 239,825 $ 124,744 $ 115,081 92.3 % Net Auction Sales $ 217,810 $ 113,050 $ 104,760 92.7 % Private Sales (2) $ 80,966 $ 168,445 $ (87,479) (51.9) % BAC Average Loan Portfolio $ 141,472 $ 72,009 $ 69,463 96.5 % June 30, 2026 2025 $ Change % Change Operational Metrics: in thousands (except percentages) BAC Loan Portfolio Balance $ 146,550 $ 84,515 $ 62,035 73.4 % N/M = Not meaningful (1) Selling expenses include direct costs associated with the sale of vehicles and memorabilia through auctions and private sales, including the purchase price and associated direct costs of inventory when Broad Arrow opportunistically purchases vehicles to be sold through auctions or private sales, as well as interest expense and borrowing costs associated with the BAC Credit Facility. (2) Private Sales is a gross transaction-volume metric that includes both brokered private sales, for which we recognize revenue on a net commission basis, and sales of our inventory, for which we recognize revenue on a gross basis. The decrease in Private Sales is primarily attributable to lower brokered private sale volume compared to the prior year, which included the private sale of a sizable single-owner collection. Because brokered private sales are recognized net, this decline did not have a proportionate impact on Marketplace revenue or income before taxes. 67 TABLE OF CONTENTS Income before taxes for the Marketplace segment was $1.8 million for the six months ended June 30, 2026, an increase of $2.3 million compared to 2025. Current period results reflect strong results at The Amelia and the Concorso d’Eleganza Villa d’Este auctions, with increases in Net Auction Sales of 90.0% and 80.3%, respectively. To a lesser extent, the increase in auction revenue is also due to the inaugural Global Icons online auction during the Salon Retromobile week in Paris and the inaugural Spring Global Icons auction. Lastly, the increase in Marketplace segment results reflects the 96.5% increase in the BAC Average Loan Portfolio Balance during the period, which was enabled by the upsizing of the BAC Credit Facility in the fourth quarter of 2025. Interest expense and other, net Six months ended June 30, 2026 2025 $ Change % Change in thousands (except percentages) Amortization of deferred LPT gain $ (2,940) $ — $ (2,940) (100.0) % Interest expense 3,377 3,907 (530) (13.6) % Change in TRA Liability — 3,078 (3,078) (100.0) % Other (income) expense 513 (350) 863 N/M Interest expense and other, net $ 950 $ 6,635 $ (5,685) (85.7) % N/M = Not meaningful Amortization of deferred LPT gain Amortization of the deferred gain associated with the LPT Agreement was $2.9 million for the six months ended June 30, 2026, with no comparable amount in the prior year period. The LPT Agreement became effective on January 1, 2026 in connection with the Markel Fronting Arrangement, and the associated deferred gain is being recognized within "Interest expense and other, net" over the expected period of future claim payments. Refer to Note 3 — Markel Fronting Arrangement in Item 1 of Part I of this Quarterly Report for additional information. Interest expense During the six months ended June 30, 2026, Interest expense decreased $0.5 million compared to 2025. This decrease is the result of a lower interest rate incurred on borrowings under the JPM Credit Facility for the six months ended June 30, 2026, when compared to the prior year. Change in TRA Liability During the six months ended June 30, 2025, we recorded $3.1 million of expense due to a change in the value of the TRA Liability. There was no such expense recorded during the six months ended June 30, 2026. The expense related to the remeasurement of the TRA Liability is recorded within "Interest expense and other, net" in the Condensed Consolidated Statements of Operations. Refer to Note 19 — Taxation in Item 1 of Part I of this Quarterly Report for additional information. Income tax (expense) benefit We are the sole managing member of THG, and as a result, consolidate its financial results. THG is treated as a partnership for U.S. federal and most applicable state and local income tax purposes. As a partnership, THG is not subject to U.S. federal and certain state and local income taxes. Any taxable income or loss generated by THG is passed through and included in the taxable income or loss of its members, including Hagerty, Inc., on a pro rata basis. Hagerty, Inc. is subject to U.S. federal, state and local income taxes with respect to its allocable share of any taxable income or loss of THG, as well as any of its stand-alone income or loss. In addition, Hagerty Insurance Holdings, Inc., Broad Arrow, Hagerty Radwood, Inc., and various foreign subsidiaries are treated as taxable entities. Hagerty Insurance Holdings, Inc. files a consolidated tax return with its wholly owned corporate subsidiaries Hagerty Re and Drivers Edge. For the six months ended June 30, 2026, we recorded an income tax benefit of $14.0 million, resulting in an effective tax rate of 74.9%, compared to income tax expense of $11.7 million for the six months ended June 30, 2025, resulting in an effective tax rate of 13.5%. The change in income tax benefit (expense) period over period is driven by non-reversing temporary differences between taxable income and pre-tax book income related to the Markel Fronting Arrangement, partially offset by higher earnings in Hagerty Re and an increase in Hagerty, Inc.'s allocable share of income from THG. 68 TABLE OF CONTENTS Non-GAAP Financial Measures Adjusted EBITDA We define EBITDA as consolidated Net income (loss), excluding Interest expense and other, net, Income tax expense (benefit), and Depreciation and amortization. We define Adjusted EBITDA as EBITDA, further adjusted to (i) exclude net investment gains and losses; (ii) deduct interest expense related to the State Farm Term Loan; (iii) exclude share-based compensation expense; and when applicable, exclude (iv) restructuring, impairment and related charges; (v) gains, losses and impairments related to divestitures; and (vi) certain other unusual items, such as Markel Fronting Arrangement transitional costs during the three and six months ended June 30, 2026. How This Measure is Useful When used in conjunction with GAAP financial measures, Adjusted EBITDA is a supplemental measure of operating performance that we believe is a useful measure to evaluate our performance period over period and relative to our competitors and peers. Management uses Adjusted EBITDA to evaluate our operating performance on a consistent basis, as it removes the impact of items not directly resulting from our core operations. We believe the presentation of Adjusted EBITDA provides securities analysts, investors, and other interested parties with a supplemental view of our operating performance that enhances their understanding of our business and our results of operations, as well as assisting investors in evaluating how well we are executing our strategic initiatives. Limitations of the Usefulness of This Measure Adjusted EBITDA may differ from similarly titled measures used by other companies due to different methods of calculation, which could reduce the usefulness of this non-GAAP financial measure when comparing our performance to that of other companies. Presentation of Adjusted EBITDA should not be considered in isolation or a substitute for, or superior to, the financial information prepared in accordance with GAAP. A reconciliation of Adjusted EBITDA to Net income (loss), the most directly comparable GAAP measure, is presented below. 69 TABLE OF CONTENTS Three months ended June 30, Six months ended June 30, 2026 2025 2026 2025 in thousands Net income (loss) $ 8,041 $ 47,202 $ (4,704) $ 74,495 Interest expense and other, net (1) 28 4,946 950 6,635 Income tax expense (benefit) (5,809) 6,161 (14,001) 11,650 Depreciation and amortization 9,716 8,833 19,422 18,321 EBITDA 11,976 67,142 1,667 111,101 Net investment gains (7,179) (1,194) (4,890) (879) Interest expense related to State Farm Term Loan (2) (515) (515) (1,030) (1,030) Share-based compensation expense 5,093 5,146 9,710 9,538 Markel Fronting Arrangement transitional costs (3) 64,111 — 153,069 — Other unusual items (4) 1,019 2,066 1,164 2,066 Adjusted EBITDA $ 74,505 $ 72,645 $ 159,690 $ 120,796 (1) Excludes interest expense related to the BAC Credit Facility, which is recorded within "Selling, general, and administrative expenses" in the Condensed Consolidated Statements of Operations. (2) Interest expense related to the State Farm Term Loan is charged against Adjusted EBITDA as it is directly attributable to the operations of Hagerty Re. Refer to Note 14 — Debt and Note 20 — Related-Party Transactions in Item 1 of Part I of this Quarterly Report for additional information. (3) Represents the amortization of deferred ceding commissions paid to Markel for policies written prior to January 1, 2026. These costs relate exclusively to policies written prior to our entry into the Markel Fronting Arrangement and are being fully amortized ratably over the remaining term of those policies through December 31, 2026. The amortization of these deferred ceding commissions was $89.0 million in the first quarter of 2026, $64.1 million in the second quarter of 2026, and we expect it to decline to approximately $37.0 million in the third quarter of 2026 and approximately $9.0 million in the fourth quarter of 2026 as the remaining 2025 policy terms run off. Management excludes these costs from Adjusted EBITDA because they are transitional charges related solely to deferred ceding commissions on policies written prior to January 1, 2026, are expected to run off by December 31, 2026, and are not indicative of our ongoing operating performance under the Markel Fronting Arrangement. (4) For the three months ended June 30, 2026, other unusual items includes professional fees related to the pending acquisition of Bennetts. For the six months ended June 30, 2026, other unusual items includes professional fees related to the pending acquisition of Bennetts and additional severance expenses associated with the actions taken in the fourth quarter of 2025. For the three and six months ended June 30, 2025, other unusual items includes certain legal settlement expenses, professional fees associated with the THG Unit Exchange and related secondary offering, and certain material severance expenses. As a result of our transition to Article 7 reporting standards, Net investment income is reported as a component of revenue and is no longer an adjustment in our reconciliation from Net income (loss) to Adjusted EBITDA. In addition, interest expense related to the State Farm Term Loan is now deducted from Adjusted EBITDA as it is directly attributable to Hagerty Re, which generates a significant portion of our net investment income. The following table presents a reconciliation of Adjusted EBITDA as presented in the prior period in accordance with Article 5, to the current presentation in accordance with Article 7: Three months ended Six months ended June 30, 2025 June 30, 2025 in thousands Prior presentation of Adjusted EBITDA $ 63,744 $ 103,352 Net investment income 9,416 18,474 Interest expense related to State Farm Term Loan (515) (1,030) Current presentation of Adjusted EBITDA $ 72,645 $ 120,796 Adjusted Net Income (Loss) and Adjusted Diluted EPS Adjusted Net Income (Loss) represents Net income (loss) attributable to Class A Common Stockholders, assuming the full exchange of all outstanding THG units and Series A Convertible Preferred Stock for shares of Class A Common Stock, adjusted to exclude (i) net investment gains and losses; and when applicable, (ii) changes in the TRA Liability; (iii) gains and losses related to divestitures; and (iv) certain other unusual items. Adjusted Diluted EPS is calculated by dividing Adjusted Net Income (Loss) by the weighted average shares of Class A Common Stock outstanding, assuming the full exchange of all outstanding THG units, Series A Convertible Preferred Stock, and unvested share-based compensation awards. 70 TABLE OF CONTENTS How These Measures Are Useful When used in conjunction with GAAP financial measures, Adjusted Net Income (Loss) and Adjusted Diluted EPS are supplemental measures of operating performance that we believe are useful measures to evaluate our performance period over period and relative to our competitors and peers. Management uses Adjusted Net Income (Loss) and Adjusted Diluted EPS to evaluate our operating performance on a consistent basis, as it removes the impact of items not directly resulting from our core operations. We believe these measures provide securities analysts, investors, and other interested parties with a supplemental view of our operating performance that enhances their understanding of our business and results of operations that may not otherwise be apparent when relying solely on GAAP measures. By assuming the full exchange of all outstanding THG units and Series A Convertible Preferred Stock, we believe these measures facilitate comparisons with other companies that have different organizational and tax structures, as well as comparisons period over period because it eliminates the effect of any changes in Net income (loss) attributable to Class A Common Stockholders driven by increases in Hagerty, Inc.'s ownership in THG, which is unrelated to our operating performance, and excludes items that are unusual or may not be indicative of our ongoing performance. Limitations of the Usefulness of These Measures Adjusted Net Income (Loss) and Adjusted Diluted EPS may differ from similarly titled measures used by other companies due to different methods of calculation, which could reduce the usefulness of this non-GAAP financial measure when comparing our performance to that of other companies. Presentation of Adjusted Net Income (Loss) and Adjusted Diluted EPS should not be considered in isolation or a substitute for, or superior to, the financial information prepared in accordance with GAAP. While these measures are useful in evaluating our performance, they assume the full exchange of all outstanding THG units and Series A Convertible Preferred Stock for shares of Class A Common Stock, which has not occurred and may not occur. Further, the adjustments made to arrive at Adjusted Net Income (Loss) exclude certain expenses and income that may recur in the future. Adjusted Net Income (Loss) and Adjusted Diluted EPS should be evaluated in conjunction with our GAAP financial results. A reconciliation of Adjusted Net Income (Loss) to Net income (loss) attributable to Class A Common Stockholders, the most directly comparable GAAP measure, and the computation of Adjusted Diluted EPS are presented below. Three months ended June 30, Six months ended June 30, 2026 2025 2026 2025 Numerator: in thousands (except per share amounts) Net income (loss) attributable to Class A Common Stockholders $ (1,668) $ 9,098 $ (8,189) $ 15,594 Adjustments: Accretion of Series A Convertible Preferred Stock 1,948 1,875 3,978 3,750 Net income (loss) attributable to non-controlling interest 7,761 36,229 (493) 55,151 Net investment gains (7,179) (1,194) (4,890) (879) Change in TRA Liability — 3,078 — 3,078 Other unusual items (1) 1,019 2,066 1,164 2,066 Tax impact of above adjustments (2) (8,069) (7,702) (10,902) (9,958) Adjusted Net Income (Loss) $ (6,188) $ 43,450 $ (19,332) $ 68,802 Denominator: Weighted average shares of Class A Common Stock outstanding — Diluted 101,797 90,698 101,418 91,247 Adjustments: Assumed exchange of non-controlling interest THG units for shares of Class A Common Stock 245,001 255,105 245,051 255,138 Assumed conversion of shares of Series A Convertible Preferred Stock into shares of Class A Common Stock 6,785 6,785 6,785 6,785 Assumed vesting of share-based compensation awards 7,951 8,580 7,979 7,404 Adjusted weighted average shares of Class A Common Stock outstanding — Diluted 361,534 361,168 361,233 360,574 Adjusted Diluted EPS $ (0.02) $ 0.12 $ (0.05) $ 0.19 71 TABLE OF CONTENTS Three months ended June 30, Six months ended June 30, 2026 2025 2026 2025 Diluted EPS $ (0.02) $ 0.09 $ (0.08) $ 0.16 Impact of assumed exchange, conversion, or vesting of remaining potentially dilutive securities (3) 0.04 0.04 0.07 0.05 Non-GAAP adjustments (4) (0.04) (0.01) (0.04) (0.02) Adjusted Diluted EPS $ (0.02) $ 0.12 $ (0.05) $ 0.19 (1) For the three months ended June 30, 2026, other unusual items includes professional fees related to the pending acquisition of Bennetts. For the six months ended June 30, 2026, other unusual items includes professional fees related to the pending acquisition of Bennetts and additional severance expenses associated with the actions taken in the fourth quarter of 2025. For the three and six months ended June 30, 2025, other unusual items includes certain legal settlement expenses, professional fees associated with the THG Unit Exchange and related secondary offering, and certain material severance expenses. (2) Represents the tax effect of the aforementioned adjustments to reflect corporate income taxes at an estimated effective tax rate of (58.0)% and 24.2% for the three months ended June 30, 2026 and 2025, respectively, and 13.8% and 23.9% for the six months ended June 30, 2026 and 2025, respectively, which considers the U.S. federal statutory rate of 21%, a combined state income tax rate of approximately 5% (net of federal benefits and required valuation allowances), and certain material permanent items. (3) Assumes the exchange of all outstanding THG units, Series A Convertible Preferred Stock, and unvested share-based compensation awards for shares of Class A Common Stock, resulting in the elimination of the non-controlling interest and recognition of the Net income (loss) attributable to non-controlling interest, as well as elimination of the accretion of Series A Convertible Preferred Stock. Refer to Note 18 — Earnings Per Share in Item 1 of Part I of this Quarterly Report for additional information on Diluted EPS. (4) Represents the per share impact of non-GAAP adjustments for each period. Refer to the reconciliation above for additional information. Liquidity and Capital Resources Maintaining a strong balance sheet and capital position is a top priority for us. As a holding company without direct operations, we manage liquidity globally and across all operating subsidiaries. Sources and Uses of Liquidity Our sources of liquidity include our: (i) balances of cash and cash equivalents; (ii) net working capital; (iii) cash flows from operations, including net investment income; (iv) borrowings from the 2025 JPM Credit Facility (as defined below) to fund the general corporate needs of THG and its subsidiaries; and (v) borrowings from the BAC Credit Facility (as defined below) to fund a portion of the lending activities of BAC. Our primary liquidity needs and capital requirements include cash required for: (i) funding the business operations of THG and its subsidiaries; (ii) funding strategic investments and acquisitions, including funding the pending acquisition of Bennetts for a purchase price of approximately £34.0 million (approximately $43.0 million as of June 30, 2026); (iii) servicing and repayment of borrowings under the 2025 JPM Credit Facility, the BAC Credit Facility, and the unsecured term loan credit facility with State Farm (the "State Farm Term Loan"); (iv) funding potential cash dividend payments on the Series A Convertible Preferred Stock; (v) payment of income taxes; (vi) funding required distributions to the non-controlling interest unit holders of THG; and (vii) funding required payments to Hagerty Holding Corp. ("HHC") and Markel (together the "Legacy Unit Holders") under the TRA. As of June 30, 2026, we believe that our sources of liquidity will be sufficient to provide an adequate level of capital to support our anticipated short and long-term commitments, operating needs, and capital requirements. Financing Arrangements 2025 JPM Credit Facility THG has a credit agreement with JPMorgan Chase Bank, N.A. ("JPM"), as administrative agent, issuing bank and swingline lender, the foreign subsidiary borrowers thereto, and the other financial institutions party thereto as lenders (the "2025 JPM Credit Agreement"). The 2025 JPM Credit Agreement provides for a senior unsecured revolving credit facility (the "2025 JPM Credit Facility") with an aggregate borrowing capacity of $375.0 million. The 2025 JPM Credit Agreement matures in March 2030, but may be extended if agreed by THG and the lenders party thereto. Any unpaid balance on the 2025 JPM Credit Facility is due at maturity. As of June 30, 2026, total outstanding borrowings under the 2025 JPM Credit Facility were $103.9 million. 72 TABLE OF CONTENTS The 2025 JPM Credit Agreement requires us to, among other things, meet certain financial covenants, including a minimum fixed charge coverage ratio test and a maximum leverage ratio test. As of June 30, 2026, we were in compliance with these financial covenants. BAC Credit Facility BAC and its wholly owned subsidiary BAC Funding 2023-1, LLC, as borrower, have a revolving credit agreement (the "BAC Credit Agreement") that provides for a revolving credit facility (the "BAC Credit Facility") with an aggregate commitment of $150.0 million. The BAC Credit Facility's borrowing base is determined by the carrying value of certain BAC notes receivable, which is then limited by the amount of the aggregate commitment. As of June 30, 2026, the applicable borrowing base for the BAC Credit Agreement was $87.5 million. The revolving borrowing period of the BAC Credit Facility expires in November 2027, followed by an amortization period until it ultimately matures in November 2028. The borrowing period and the maturity date of the BAC Credit Facility may be extended by one year if requested by BAC and agreed by the administrative agent. BAC is not a borrower or guarantor of the BAC Credit Facility. BAC and certain of its subsidiaries may transfer notes receivable to wholly owned, bankruptcy remote special purpose entities (each, an "SPE") to secure borrowings, isolating these assets from our other obligations. Recourse is limited to (i) an obligation of the applicable seller to repurchase a note receivable if it is determined that there was a breach of any representation or warranty relating to such note receivable as of the relevant date specified in the related transfer agreement; and (ii) a limited guarantee for certain liabilities that may result under certain foreign exchange hedging activity of one of the SPEs. BAC and BAC Funding 2023-1, LLC are required, among other things, to meet certain financial covenants including that BAC, as the servicer, maintain a minimum tangible net worth, minimum liquidity balances, and an indebtedness to tangible net worth ratio. As of June 30, 2026, we were in compliance with the financial covenants under the BAC Credit Agreement. Refer to Note 14 — Debt in Item 1 of Part I of this Quarterly Report for additional information related to the 2025 JPM Credit Agreement and BAC Credit Agreement. Capital and Dividend Restrictions We are a holding company with no material assets other than our ownership interest in THG and its operating subsidiaries. Accordingly, our ability to meet our cash requirements depends on THG's financial performance and the distributions we receive from THG. Our subsidiaries' ability to make distributions, pay dividends and make other payments may be regulated by the states and territories where they are domiciled. For example, as described below, our ability to upstream capital from Hagerty Re is subject to Bermuda regulatory capital requirements and dividend restrictions administered by the Bermuda Monetary Authority ("BMA"), which may limit distributions in certain periods. For a discussion of the risks associated with our holding company structure, refer to Item 1A. Risk Factors — Risks Related to Tax — "Hagerty, Inc. is a holding company, whose only material asset is its interest in THG. Hagerty, Inc. depends on THG distributions to pay taxes, make payments under the TRA, and pay other expenses." in our Annual Report. Capital Restrictions Our reinsurance subsidiary, Hagerty Re, is subject to the Bermuda Solvency Capital Requirement ("BSCR"), which establishes a target capital level and enhanced capital requirements for each insurer. As of June 30, 2026, Hagerty Re maintained sufficient statutory capital and surplus to comply with the BSCR. Similarly, our U.S. insurance company subsidiary, Drivers Edge, which holds certificates of authority in 42 states, is subject to state-specific minimum capital and surplus requirements, as well as risk-based capital ("RBC") requirements. RBC levels are reported on an annual basis. As of June 30, 2026, Drivers Edge maintained sufficient capital and surplus levels to comply with National Association of Insurance Commissioners and state insurance regulations. Dividend Restrictions Under Bermuda law, Hagerty Re is prohibited from declaring or issuing a dividend if it fails to meet its minimum solvency margin or minimum liquidity ratio. Prior approval from the BMA is also required if Hagerty Re's proposed dividend payments would exceed 25% of its prior year-end total statutory capital and surplus. Based on these restrictions, during 2026, Hagerty Re can pay $95.4 million in dividends without prior BMA approval. As of June 30, 2026, there were no plans to issue dividends from Hagerty Re. 73 TABLE OF CONTENTS Similarly, state statutes restrict the amount of dividends that Drivers Edge may pay without prior approval of state insurance regulators. As of June 30, 2026, there were no plans to issue dividends from Drivers Edge and a change in such plans may require regulatory approval. Comparative Cash Flows The following table summarizes our cash flow data for the six months ended June 30, 2026 and 2025: Six months ended June 30, 2026 2025 $ Change % Change in thousands (except percentages) Net Cash Provided by Operating Activities $ 186,157 $ 97,714 $ 88,443 90.5 % Net Cash Used in Investing Activities $ (82,702) $ (31,839) $ (50,863) 159.8 % Net Cash Provided by Financing Activities $ 65,336 $ 29,480 $ 35,856 121.6 % Operating Activities Cash provided by operating activities primarily consists of Net income (loss), adjusted for non-cash items, and changes in working capital balances. Net cash provided by operating activities for the six months ended June 30, 2026 and 2025 is presented below: Six months ended June 30, 2026 2025 $ Change % Change in thousands (except percentages) Net income (loss) $ (4,704) $ 74,495 $ (79,199) (106.3) % Non-cash adjustments to Net income (loss) (1,064) 35,595 (36,659) (103.0) % Changes in operating assets and liabilities 191,925 (12,376) 204,301 N/M Net Cash Provided by Operating Activities $ 186,157 $ 97,714 $ 88,443 90.5 % N/M = Not meaningful Net cash provided by operating activities for the six months ended June 30, 2026 was $186.2 million, an increase of $88.4 million, or 90.5%, compared to 2025. This increase was due to a $204.3 million increase in cash from operating assets and liabilities, partially offset by a $115.9 million decrease in Net income (loss), net of non-cash adjustments. The increase in operating cash flows is primarily driven by our entry into the Markel Fronting Arrangement, which became effective on January 1, 2026 and increased Hagerty Re's U.S. quota share from approximately 80% to 100%, including for in-force policies written in 2025. In connection with the increase in quota share for in-force 2025 policies, we received cash consideration of $53.7 million, representing the unearned premium for the associated unexpired risk period. In addition, as a result of the Markel Fronting Arrangement, premiums and losses are now settled monthly rather than quarterly under the prior contractual arrangement. To a lesser extent, the increase in operating cash flows is driven by growth in subject premiums written through our MGA subsidiaries. Investing Activities Cash used in investing activities for the six months ended June 30, 2026 increased by $50.9 million when compared to 2025. This increase is principally due to a $27.6 million increase in net purchasing activity related to our investment portfolio and, to a lesser extent, an $18.4 million increase in net fundings of BAC notes receivable. Financing Activities Cash from financing activities for the six months ended June 30, 2026 increased by $35.9 million when compared to 2025, principally due to the LPT Agreement with Markel, which resulted in a $50.5 million cash proceeds. Also favorably impacting the comparison is a $30.4 million payment to THG non-controlling interest unit holders in 2025 for which there was no comparable payment in 2026. These increases were partially offset by a $28.8 million decrease in net proceeds received from credit facility borrowings. 74 TABLE OF CONTENTS Tax Receivable Agreement In connection with the consummation of the business combination that formed Hagerty, Inc. in 2021, Hagerty, Inc. entered into a TRA with the Legacy Unit Holders. The TRA requires us to pay the Legacy Unit Holders 85% of the U.S. federal, state, and local cash tax savings realized by Hagerty, Inc. resulting from increases in tax basis and certain other tax benefits, as outlined in the Business Combination Agreement, upon the exchange of THG units and shares of Hagerty, Inc. Class V Common Stock for shares of Hagerty, Inc. Class A Common Stock or cash. The amount and timing of any payments under the TRA will vary depending on a number of factors, including, but not limited to, the increase in tax basis of THG's assets, the timing of any future redemptions, exchanges or purchases of THG units held by Legacy Unit Holders, the price of Hagerty, Inc. Class A Common Stock at the time of the redemption, exchange or purchase, the extent to which redemptions or exchanges are taxable, the amount and timing of the taxable income that Hagerty, Inc. generates in the future, the tax rates then applicable, and the portion of the payments under the TRA constituting imputed interest. We expect to have adequate capital resources to meet the requirements and obligations under the TRA entered into with the Legacy Unit Holders. Refer to Note 19 — Taxation in Item 1 of Part I of this Quarterly Report for information related to the TRA. Critical Accounting Policies and Estimates The preparation of the unaudited Condensed Consolidated Financial Statements in accordance with GAAP requires management to make significant judgments, assumptions, and estimates that materially affect the amounts reported in our Condensed Consolidated Financial Statements. Management's judgments, assumptions, and estimates are based on historical experience, future expectations, and other factors that are believed to be reasonable as of the date of the Condensed Consolidated Financial Statements. Actual results may ultimately differ from management's original estimates, as future events and circumstances sometimes do not develop as expected. Our accounting policies are set forth in Note 2 — Summary of Significant Accounting Policies to Consolidated Financial Statements contained in our Annual Report. New Accounting Standards New accounting standards are described in Note 2 — Summary of Significant Accounting Policies in Item 1 of Part I of this Quarterly Report, which are incorporated herein by reference.