HGTY

SEC source: 0001628280-26-065056 · wk-form4_1791234905.xml · nonDerivative · entry 2

Chafey Diana · CIK 0001867966 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 76,911

F2 · shares: Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of April 1, 2026 through September 30, 2026.

F3 · price: In accordance with the ESPP, the per share price paid for these shares was an amount equal to 95% of the closing price of the Issuer's stock on October 1, 2026.

SEC source: 0001628280-26-065044 · wk-form4_1791234799.xml · nonDerivative · entry 1

McClymont Patrick · CIK 0001589119 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 337,986

F1 · shares: Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of April 1, 2026 through September 30, 2026.

F2 · price: In accordance with the ESPP, the per share price paid for these shares was an amount equal to 95% of the closing price of the Issuer's stock on October 1, 2026.

SEC source: 0001628280-26-065056 · wk-form4_1791234905.xml · nonDerivative · entry 1

Chafey Diana · CIK 0001867966 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 75,932

F1 · shares: Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to Reporting Person's RSU award agreement with a grant date of October 1, 2023.

SEC source: 0001628280-26-065042 · wk-form4_1791234741.xml · nonDerivative · entry 1

DELANEY KEVIN M · CIK 0001398794 · Chief Accounting Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 83,013

F1 · shares: Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of restricted stock units ("RSUs") pursuant to the RSU Agreement between the Issuer and the Reporting Person dated as of October 1, 2025.

SEC source: 0001628280-26-063585 · wk-form4_1790367698.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 674,097

F1 · kind: Represents a bona fide gift to a charitable organization.

F2 · ownership.direct: Held by Aldel LLC. The Reporting Person is the manager of Aldel LLC and has voting and investment discretion with respect to the securities held of record by Aldel LLC. The Reporting Person disclaims beneficial ownership of the reported securities except to the extent of his pecuniary interest therein.

SEC source: 0000905148-26-004168 · form4.xml · derivative · entry 2

MARKEL GROUP INC. · CIK 0001096343 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 67,163,589

Underlying: Class A Common Stock · 7,836,411 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each share of Class V Common Stock is paired with one unit of limited liability company interest of The Hagerty Group, LLC (each, an "OpCo Unit" and, together with each corresponding share of Class V Common Stock, a "Paired Interest"). Each Paired Interest has no expiration date and is exchangeable, at the option of the holder, on a one-for-one basis for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, an equivalent value in cash, pursuant to the Exchange Agreement, dated as of December 2, 2021, and amended and restated as of March 23, 2022, among the Reporting Person, The Hagerty Group, LLC, Hagerty Holding Corp., and the Issuer (the "Amended and Restated Exchange Agreement"). Each share of Class V Common Stock has no incidents of economic ownership and has ten (10) votes per share until the earlier of (i) December 2, 2036, and (ii) transfer to a non-qualified transferee, after which it has one (1) vote per share.

F2 · kind: In connection with an underwritten secondary offering of shares of Class A Common Stock by Hagerty Holding Corp. that closed on September 11, 2026, and pursuant to the terms of the Amended and Restated Exchange Agreement, the Reporting Person exchanged 7,836,411 Paired Interests for, at the election of the Issuer, an equal number of shares of Class A Common Stock.

F1 · price: Each share of Class V Common Stock is paired with one unit of limited liability company interest of The Hagerty Group, LLC (each, an "OpCo Unit" and, together with each corresponding share of Class V Common Stock, a "Paired Interest"). Each Paired Interest has no expiration date and is exchangeable, at the option of the holder, on a one-for-one basis for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, an equivalent value in cash, pursuant to the Exchange Agreement, dated as of December 2, 2021, and amended and restated as of March 23, 2022, among the Reporting Person, The Hagerty Group, LLC, Hagerty Holding Corp., and the Issuer (the "Amended and Restated Exchange Agreement"). Each share of Class V Common Stock has no incidents of economic ownership and has ten (10) votes per share until the earlier of (i) December 2, 2036, and (ii) transfer to a non-qualified transferee, after which it has one (1) vote per share.

F1 · derivative.exercise_date: Each share of Class V Common Stock is paired with one unit of limited liability company interest of The Hagerty Group, LLC (each, an "OpCo Unit" and, together with each corresponding share of Class V Common Stock, a "Paired Interest"). Each Paired Interest has no expiration date and is exchangeable, at the option of the holder, on a one-for-one basis for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, an equivalent value in cash, pursuant to the Exchange Agreement, dated as of December 2, 2021, and amended and restated as of March 23, 2022, among the Reporting Person, The Hagerty Group, LLC, Hagerty Holding Corp., and the Issuer (the "Amended and Restated Exchange Agreement"). Each share of Class V Common Stock has no incidents of economic ownership and has ten (10) votes per share until the earlier of (i) December 2, 2036, and (ii) transfer to a non-qualified transferee, after which it has one (1) vote per share.

F1 · derivative.expiration_date: Each share of Class V Common Stock is paired with one unit of limited liability company interest of The Hagerty Group, LLC (each, an "OpCo Unit" and, together with each corresponding share of Class V Common Stock, a "Paired Interest"). Each Paired Interest has no expiration date and is exchangeable, at the option of the holder, on a one-for-one basis for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, an equivalent value in cash, pursuant to the Exchange Agreement, dated as of December 2, 2021, and amended and restated as of March 23, 2022, among the Reporting Person, The Hagerty Group, LLC, Hagerty Holding Corp., and the Issuer (the "Amended and Restated Exchange Agreement"). Each share of Class V Common Stock has no incidents of economic ownership and has ten (10) votes per share until the earlier of (i) December 2, 2036, and (ii) transfer to a non-qualified transferee, after which it has one (1) vote per share.

SEC source: 0000905148-26-004168 · form4.xml · nonDerivative · entry 1

MARKEL GROUP INC. · CIK 0001096343 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,944,411

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · kind: In connection with an underwritten secondary offering of shares of Class A Common Stock by Hagerty Holding Corp. that closed on September 11, 2026, and pursuant to the terms of the Amended and Restated Exchange Agreement, the Reporting Person exchanged 7,836,411 Paired Interests for, at the election of the Issuer, an equal number of shares of Class A Common Stock.

F1 · price: Each share of Class V Common Stock is paired with one unit of limited liability company interest of The Hagerty Group, LLC (each, an "OpCo Unit" and, together with each corresponding share of Class V Common Stock, a "Paired Interest"). Each Paired Interest has no expiration date and is exchangeable, at the option of the holder, on a one-for-one basis for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, an equivalent value in cash, pursuant to the Exchange Agreement, dated as of December 2, 2021, and amended and restated as of March 23, 2022, among the Reporting Person, The Hagerty Group, LLC, Hagerty Holding Corp., and the Issuer (the "Amended and Restated Exchange Agreement"). Each share of Class V Common Stock has no incidents of economic ownership and has ten (10) votes per share until the earlier of (i) December 2, 2036, and (ii) transfer to a non-qualified transferee, after which it has one (1) vote per share.

SEC source: 0001104659-26-107145 · tm2625312-2_4seq1.xml · derivative · entry 6

Hagerty Holding Corp. · CIK 0001899295 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 155,914,656

Underlying: Class A Common Stock · 1,387,500 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: Each Paired Interest has no expiration date and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

F2 · price: 1,387,500 shares of Class A Common Stock were issued to the Reporting Person in exchange for an equal number of Paired Interests that were surrendered by the Reporting Person pursuant to the Exchange Agreement.

F3 · derivative.exercise_date: Each Paired Interest has no expiration date and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

F3 · derivative.expiration_date: Each Paired Interest has no expiration date and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

SEC source: 0001104659-26-107145 · tm2625312-2_4seq1.xml · nonDerivative · entry 4

Hagerty Holding Corp. · CIK 0001899295 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

SEC source: 0001104659-26-107145 · tm2625312-2_4seq1.xml · nonDerivative · entry 3

Hagerty Holding Corp. · CIK 0001899295 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,387,500

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · price: 1,387,500 shares of Class A Common Stock were issued to the Reporting Person in exchange for an equal number of Paired Interests that were surrendered by the Reporting Person pursuant to the Exchange Agreement.

SEC source: 0001104659-26-107145 · tm2625312-2_4seq1.xml · derivative · entry 5

Hagerty Holding Corp. · CIK 0001899295 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 157,302,156

Underlying: Class A Common Stock · 9,250,000 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: Each Paired Interest has no expiration date and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

F1 · price: 9,250,000 shares of Class A Common Stock were issued to the Reporting Person in exchange for an equal number of Paired Interests (as defined below) that were surrendered by the Reporting Person pursuant to the Amended and Restated Exchange Agreement, dated as of December 2, 2021 and amended and restated as of March 23, 2022 (the "Exchange Agreement"), among the Issuer, The Hagerty Group, LLC ("OpCo"), the Reporting Person, Markel Corporation ("Markel") and each of the Reporting Person's and Markel's Qualified Transferees (as defined therein). Each "Paired Interest" consists of one share of Class V Common Stock of the Issuer and one unit of limited liability company interest of OpCo and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

F3 · derivative.exercise_date: Each Paired Interest has no expiration date and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

F3 · derivative.expiration_date: Each Paired Interest has no expiration date and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

SEC source: 0001104659-26-107145 · tm2625312-2_4seq1.xml · nonDerivative · entry 2

Hagerty Holding Corp. · CIK 0001899295 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

SEC source: 0001104659-26-107145 · tm2625312-2_4seq1.xml · nonDerivative · entry 1

Hagerty Holding Corp. · CIK 0001899295 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,250,000

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 9,250,000 shares of Class A Common Stock were issued to the Reporting Person in exchange for an equal number of Paired Interests (as defined below) that were surrendered by the Reporting Person pursuant to the Amended and Restated Exchange Agreement, dated as of December 2, 2021 and amended and restated as of March 23, 2022 (the "Exchange Agreement"), among the Issuer, The Hagerty Group, LLC ("OpCo"), the Reporting Person, Markel Corporation ("Markel") and each of the Reporting Person's and Markel's Qualified Transferees (as defined therein). Each "Paired Interest" consists of one share of Class V Common Stock of the Issuer and one unit of limited liability company interest of OpCo and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

SEC source: 0001628280-26-047271 · wk-form4_1783369055.xml · nonDerivative · entry 1

DELANEY KEVIN M · CIK 0001398794 · Chief Accounting Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 83,972

F1 · shares: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 5, 2026.

SEC source: 0001628280-26-046994 · wk-form4_1783025243.xml · nonDerivative · entry 1

Briglia Jeffrey Edward · CIK 0002025736 · President of Insurance

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 157,135

F1 · shares: Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of restricted stock units ("RSUs") pursuant to the RSU Agreement between the Issuer and the Reporting Person dated as of July 1, 2024.

SEC source: 0001628280-26-046991 · wk-form4_1783025185.xml · nonDerivative · entry 3

DELANEY KEVIN M · CIK 0001398794 · Chief Accounting Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 87,085

F4 · shares: Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of restricted stock units ("RSUs") pursuant to the RSU Agreement between the Issuer and the Reporting Person dated as of July 1, 2023.

SEC source: 0001628280-26-046991 · wk-form4_1783025185.xml · nonDerivative · entry 2

DELANEY KEVIN M · CIK 0001398794 · Chief Accounting Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 89,610

F1 · shares: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 5, 2026.

F3 · price: This transaction was executed in multiple trades at prices ranging from $12.00 to $12.23. The price reported above reflects the weighted average purchase price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

SEC source: 0001628280-26-046992 · wk-form4_1783025211.xml · nonDerivative · entry 1

Bjornstad Henrik Waersted · CIK 0002128701 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,114

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on July 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

SEC source: 0001628280-26-046991 · wk-form4_1783025185.xml · nonDerivative · entry 1

DELANEY KEVIN M · CIK 0001398794 · Chief Accounting Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 99,050

F1 · shares: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 5, 2026.

F2 · price: This transaction was executed in multiple trades at prices ranging from $12.00 to $12.03. The price reported above reflects the weighted average purchase price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

SEC source: 0001628280-26-036455 · wk-form4_1779221728.xml · nonDerivative · entry 1

Kuczinski Anthony J · CIK 0001976607 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 68,648

F1 · price: This transaction was executed in multiple trades at prices ranging from $10.44 to $10.46. The price reported above reflects the weighted average purchase price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

SEC source: 0001628280-26-024271 · wk-form4_1775681404.xml · nonDerivative · entry 1

Harris Laurie · CIK 0001783632 · Director

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 36,689

F1 · kind: The sale occurred automatically pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on November 10, 2025, and does not represent a discretionary transaction. The reported sale represents a "sell to cover" transaction and equals the number of shares required to be sold by the Reporting Person to satisfy tax withholding obligations in connection with the vesting of the Reporting Person's restricted stock units.

F2 · price: This transaction was executed in multiple trades at prices ranging from $10.91 to $11.10. The price reported above reflects the weighted average purchase price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

SEC source: 0001628280-26-023588 · wk-form4_1775242081.xml · nonDerivative · entry 3

McClymont Patrick · CIK 0001589119 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 336,794

F3 · shares: Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of October 1, 2025 through March 31, 2026.

F4 · price: In accordance with the ESPP, the per share price paid for these shares was an amount equal to 95% of the closing price of the Issuer's stock on April 1, 2026.

SEC source: 0001628280-26-023585 · wk-form4_1775242064.xml · nonDerivative · entry 3

Chafey Diana · CIK 0001867966 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 77,008

F3 · shares: Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of October 1, 2025 through March 31, 2026.

F4 · price: In accordance with the ESPP, the per share price paid for these shares was an amount equal to 95% of the closing price of the Issuer's stock on April 1, 2026.

SEC source: 0001628280-26-023589 · wk-form4_1775242087.xml · nonDerivative · entry 2

Champagne Collette · CIK 0001897817 · CHRO and CAO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 270,207

F2 · shares: Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements.

SEC source: 0001628280-26-023589 · wk-form4_1775242087.xml · nonDerivative · entry 1

Champagne Collette · CIK 0001897817 · CHRO and CAO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 298,485

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

SEC source: 0001628280-26-023590 · wk-form4_1775242093.xml · nonDerivative · entry 1

Hagerty McKeel · CIK 0001897880 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,037,740

F1 · shares: Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of restricted stock units ("RSUs") pursuant to various RSU award agreements.

SEC source: 0001628280-26-023594 · wk-form4_1775242122.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 79,173

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

SEC source: 0001628280-26-023583 · wk-form4_1775242053.xml · nonDerivative · entry 2

Briglia Jeffrey Edward · CIK 0002025736 · President of Insurance

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 162,027

F2 · shares: Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements.

SEC source: 0001628280-26-023583 · wk-form4_1775242053.xml · nonDerivative · entry 1

Briglia Jeffrey Edward · CIK 0002025736 · President of Insurance

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 171,926

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

SEC source: 0001628280-26-023587 · wk-form4_1775242076.xml · nonDerivative · entry 2

Page Russell Andrew · CIK 0002020291 · Chief Information Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 131,743

F2 · shares: Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements.

SEC source: 0001628280-26-023587 · wk-form4_1775242076.xml · nonDerivative · entry 1

Page Russell Andrew · CIK 0002020291 · Chief Information Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 142,889

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

SEC source: 0001628280-26-023592 · wk-form4_1775242107.xml · nonDerivative · entry 1

Kuczinski Anthony J · CIK 0001976607 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 59,148

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

SEC source: 0001628280-26-023586 · wk-form4_1775242069.xml · nonDerivative · entry 1

Salmi Mika · CIK 0001897885 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 54,173

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

SEC source: 0001628280-26-023591 · wk-form4_1775242099.xml · nonDerivative · entry 2

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 127,115

F2 · shares: Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements

SEC source: 0001628280-26-023591 · wk-form4_1775242099.xml · nonDerivative · entry 1

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 136,742

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

SEC source: 0001628280-26-023581 · wk-form4_1775242040.xml · nonDerivative · entry 1

Heaton Michael R · CIK 0001751668 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,101

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

SEC source: 0001628280-26-023593 · wk-form4_1775242114.xml · nonDerivative · entry 1

SWANSON WILLIAM H · CIK 0001194790 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 54,173

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

SEC source: 0001628280-26-023584 · wk-form4_1775242058.xml · nonDerivative · entry 2

DELANEY KEVIN M · CIK 0001398794 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 99,955

F2 · shares: Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements.

SEC source: 0001628280-26-023584 · wk-form4_1775242058.xml · nonDerivative · entry 1

DELANEY KEVIN M · CIK 0001398794 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 108,411

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

SEC source: 0001628280-26-023588 · wk-form4_1775242081.xml · nonDerivative · entry 2

McClymont Patrick · CIK 0001589119 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 335,832

F2 · shares: Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements.

SEC source: 0001628280-26-023588 · wk-form4_1775242081.xml · nonDerivative · entry 1

McClymont Patrick · CIK 0001589119 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 368,220

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

SEC source: 0001628280-26-023582 · wk-form4_1775242046.xml · nonDerivative · entry 1

Harris Laurie · CIK 0001783632 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 42,220

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

SEC source: 0001628280-26-023601 · wk-form4_1775242679.xml · nonDerivative · entry 1

Kay Sabrina · CIK 0001835895 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 54,173

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

SEC source: 0001628280-26-023595 · wk-form4_1775242132.xml · nonDerivative · entry 1

Harbert Randall Houston · CIK 0001968486 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 45,832

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

SEC source: 0001628280-26-023585 · wk-form4_1775242064.xml · nonDerivative · entry 2

Chafey Diana · CIK 0001867966 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 75,843

F2 · shares: Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements.

SEC source: 0001628280-26-023585 · wk-form4_1775242064.xml · nonDerivative · entry 1

Chafey Diana · CIK 0001867966 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 80,676

F1 · shares: Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

SEC source: 0001628280-26-017804 · wk-form4_1773439835.xml · nonDerivative · entry 1

Kuczinski Anthony J · CIK 0001976607 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 47,277

SEC source: 0001628280-26-014655 · wk-form4_1772659797.xml · nonDerivative · entry 1

Kuczinski Anthony J · CIK 0001976607 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 43,277

F1 · price: This transaction was executed in multiple trades at prices ranging from $10.45 to $10.92. The price reported above reflects the weighted average purchase price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

SEC source: 0001628280-26-003646 · wk-form4_1769549934.xml · derivative · entry 4

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 775,213

Underlying: Class A Common Stock · 50,000 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Quadrifoglio Holdings LLC received 2,044,272 Common Units of The Hagerty Group, LLC (the "Restricted Units") pursuant to the terms of that certain Contribution and Exchange Agreement, dated as of August 9, 2022, among the Issuer and the parties thereto. The Restricted Units are subject to exchange restrictions that release in five equal installments on April 1st of each year (which began on April 1, 2023) (all Restricted Units that have been released from the exchange restrictions are referred to herein as the "Released Units"). The reported transaction reflects the conversion of 50,000 Released Units owned by Quadrifoglio Holdings LLC into shares of the Issuer's Class A Common Stock pursuant to that certain Exchange Agreement, dated as of August 9, 2022, by and among the Issuer and the parties thereto (the "Conversion"). After the Conversion, Quadrifoglio Holdings LLC owns 775,213 Released Units.

F1 · derivative.exercise_date: Quadrifoglio Holdings LLC received 2,044,272 Common Units of The Hagerty Group, LLC (the "Restricted Units") pursuant to the terms of that certain Contribution and Exchange Agreement, dated as of August 9, 2022, among the Issuer and the parties thereto. The Restricted Units are subject to exchange restrictions that release in five equal installments on April 1st of each year (which began on April 1, 2023) (all Restricted Units that have been released from the exchange restrictions are referred to herein as the "Released Units"). The reported transaction reflects the conversion of 50,000 Released Units owned by Quadrifoglio Holdings LLC into shares of the Issuer's Class A Common Stock pursuant to that certain Exchange Agreement, dated as of August 9, 2022, by and among the Issuer and the parties thereto (the "Conversion"). After the Conversion, Quadrifoglio Holdings LLC owns 775,213 Released Units.

F1 · derivative.expiration_date: Quadrifoglio Holdings LLC received 2,044,272 Common Units of The Hagerty Group, LLC (the "Restricted Units") pursuant to the terms of that certain Contribution and Exchange Agreement, dated as of August 9, 2022, among the Issuer and the parties thereto. The Restricted Units are subject to exchange restrictions that release in five equal installments on April 1st of each year (which began on April 1, 2023) (all Restricted Units that have been released from the exchange restrictions are referred to herein as the "Released Units"). The reported transaction reflects the conversion of 50,000 Released Units owned by Quadrifoglio Holdings LLC into shares of the Issuer's Class A Common Stock pursuant to that certain Exchange Agreement, dated as of August 9, 2022, by and among the Issuer and the parties thereto (the "Conversion"). After the Conversion, Quadrifoglio Holdings LLC owns 775,213 Released Units.

SEC source: 0001628280-26-003646 · wk-form4_1769549934.xml · nonDerivative · entry 2

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 0

F3 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 15, 2025.

F4 · price: This transaction was executed in multiple trades at prices ranging from $12.30 to $12.67. The price reported above reflects the weighted average purchase price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

F2 · ownership.nature: The Reporting Person is the sole member of Quadrifoglio Holdings LLC and has voting and investment discretion with respect to the securities held of record by Quadrifoglio Holdings LLC. The Reporting Person disclaims beneficial ownership of the reported securities except to the extent of his pecuniary interest therein.