HGTY

SEC source: 0001976607-25-000003 · wk-form4_1757362621.xml · nonDerivative · entry 1

Kuczinski Anthony J · CIK 0001976607 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 28,277

F1 · price: This transaction was executed in multiple trades at prices ranging from $11.57 to $11.65. 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: 0001124462-25-000015 · wk-form4_1756931615.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,288,529

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F5 · price: This transaction was executed in multiple trades at prices ranging from $11.11 to $11.48. 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.

F3 · 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: 0001124462-25-000015 · wk-form4_1756931615.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,330,228

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $11.10 to $11.25. 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.

F3 · 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: 0001124462-25-000015 · wk-form4_1756931615.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,352,523

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $11.07 to $11.43. 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.

F3 · 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: 0001124462-25-000013 · wk-form4_1756412740.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,415,023

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F5 · price: This transaction was executed in multiple trades at prices ranging from $11.08 to $11.40. 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.

F3 · 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: 0001124462-25-000013 · wk-form4_1756412740.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,443,759

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $10.96 to $11.25. 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.

F3 · 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: 0001124462-25-000013 · wk-form4_1756412740.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,472,463

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $10.62 to $10.89. 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.

F3 · 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: 0001124462-25-000011 · wk-form4_1756153356.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,482,307

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F5 · price: This transaction was executed in multiple trades at prices ranging from $10.79 to $11.01. 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.

F3 · 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: 0001124462-25-000011 · wk-form4_1756153356.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,489,975

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $10.71 to $11.02. 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.

F3 · 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: 0001124462-25-000011 · wk-form4_1756153356.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,496,056

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $10.67 to $10.91. 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.

F3 · 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: 0001840776-25-000223 · wk-form4_1755118565.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,503,412

F4 · kind: The shares covered herein were disposed of in connection with the exercise in full of the option to purchase additional shares granted to the underwriters pursuant to the underwriting agreement for the Offering.

F2 · price: The price of $8.9197 represents the $9.34 secondary public offering price per share, less the underwriting discounts and commissions of $0.4203 per share, for shares sold in connection with the Offering.

F3 · 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: 0001104659-25-079366 · tm2523642-1_4seq1.xml · derivative · entry 3

Hagerty Holding Corp. · CIK 0001899295 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 166,552,156

Underlying: Class A Common Stock · 1,236,750 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.

F2 · 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: 1,236,750 shares of Class A Common Stock were issued 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.

F2 · 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.

F2 · 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: 0001104659-25-079366 · tm2523642-1_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: 0001104659-25-079366 · tm2523642-1_4seq1.xml · nonDerivative · entry 1

Hagerty Holding Corp. · CIK 0001899295 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,236,750

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: 1,236,750 shares of Class A Common Stock were issued 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: 0001840776-25-000223 · wk-form4_1755118565.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,721,662

F1 · kind: The shares covered herein were disposed of pursuant to a registered secondary offering (the "Offering") contemplated by the prospectus included in the Issuer's registration statement on Form S-3, as originally filed on Form S-1 (File No. 333-261810).

F2 · price: The price of $8.9197 represents the $9.34 secondary public offering price per share, less the underwriting discounts and commissions of $0.4203 per share, for shares sold in connection with the Offering.

F3 · 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: 0001104659-25-076145 · tm2523060-1_4seq1.xml · derivative · entry 3

Hagerty Holding Corp. · CIK 0001899295 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 167,788,906

Underlying: Class A Common Stock · 8,245,000 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.

F2 · 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: 8,245,000 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.

F2 · 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.

F2 · 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: 0001104659-25-076145 · tm2523060-1_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: 0001104659-25-076145 · tm2523060-1_4seq1.xml · nonDerivative · entry 1

Hagerty Holding Corp. · CIK 0001899295 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,245,000

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: 8,245,000 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: 0001840776-25-000215 · wk-form4_1753823954.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,176,662

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $10.75 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.

F3 · 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: 0001840776-25-000215 · wk-form4_1753823954.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,180,662

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $10.62 to $10.87. 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.

F3 · 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: 0001840776-25-000211 · wk-form4_1753388377.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,205,390

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F5 · price: This transaction was executed in multiple trades at prices ranging from $10.19 to $10.63. 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.

F3 · 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: 0001840776-25-000211 · wk-form4_1753388377.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,315,990

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $10.08 to $10.28. 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.

F3 · 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: 0001840776-25-000211 · wk-form4_1753388377.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,356,383

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $10.12 to $10.24. 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.

F3 · 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: 0001840776-25-000205 · wk-form4_1753129898.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,388,252

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F5 · price: This transaction was executed in multiple trades at prices ranging from $10.02 to $10.19. 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.

F3 · 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: 0001840776-25-000205 · wk-form4_1753129898.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,405,149

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $10.04 to $10.17. 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.

F3 · 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: 0001840776-25-000205 · wk-form4_1753129898.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,441,323

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $9.99 to $10.09. 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.

F3 · 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: 0001840776-25-000199 · wk-form4_1752697613.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,459,085

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F5 · price: This transaction was executed in multiple trades at prices ranging from $9.91 to $10.13. 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.

F3 · 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: 0001840776-25-000199 · wk-form4_1752697613.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,476,057

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $9.92 to $10.14. 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.

F3 · 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: 0001840776-25-000199 · wk-form4_1752697613.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,490,919

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $9.97 to $10.04. 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.

F3 · 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: 0001840776-25-000196 · wk-form4_1752268117.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,499,281

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F5 · price: This transaction was executed in multiple trades at prices ranging from $9.81 to $10.06. 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.

F3 · 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: 0001840776-25-000196 · wk-form4_1752268117.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,509,251

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $10.01 to $10.16. 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.

F3 · 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: 0001840776-25-000196 · wk-form4_1752268117.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,550,490

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $9.99 to $10.11. 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.

F3 · 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: 0001840776-25-000194 · wk-form4_1752007951.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,649,256

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F5 · price: This transaction was executed in multiple trades at prices ranging from $10.09 to $10.24. 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.

F3 · 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: 0001840776-25-000194 · wk-form4_1752007951.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,661,721

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $10.11 to $10.19. 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.

F3 · 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: 0001840776-25-000194 · wk-form4_1752007951.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,671,635

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $10.00 to $10.23. 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.

F3 · 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: 0001840776-25-000186 · wk-form4_1751489354.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,674,735

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F5 · price: This transaction was executed in multiple trades at prices ranging from $9.91 to $10.22. 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.

F3 · 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: 0001840776-25-000186 · wk-form4_1751489354.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,687,235

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $9.99 to $10.23. 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.

F3 · 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: 0001840776-25-000188 · wk-form4_1751493971.xml · nonDerivative · entry 1

Briglia Jeffrey Edward · CIK 0002025736 · President of Insurance

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 125,629

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: 0001840776-25-000190 · wk-form4_1751494096.xml · nonDerivative · entry 1

DELANEY KEVIN M · CIK 0001398794 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 82,491

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, 2023.

SEC source: 0001840776-25-000192 · wk-form4_1751573714.xml · nonDerivative · entry 1

Heaton Michael R · CIK 0001751668 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,230

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, 2026, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

SEC source: 0001840776-25-000186 · wk-form4_1751489354.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,694,235

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $10.00 to $10.17. 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.

F3 · 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: 0001840776-25-000184 · wk-form4_1751055695.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,698,835

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F5 · price: This transaction was executed in multiple trades at prices ranging from $9.97 to $10.22. 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.

F3 · 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: 0001840776-25-000184 · wk-form4_1751055695.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,706,267

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $9.98 to $10.21. 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.

F3 · 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: 0001840776-25-000184 · wk-form4_1751055695.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,725,894

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $10.00 to $10.11. 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.

F3 · 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: 0001840776-25-000182 · wk-form4_1750798040.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,738,504

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F5 · price: This transaction was executed in multiple trades at prices ranging from $10.03 to $10.23. 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.

F3 · 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: 0001840776-25-000182 · wk-form4_1750798040.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,769,614

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $9.80 to $10.09. 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.

F3 · 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: 0001840776-25-000182 · wk-form4_1750798040.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,781,324

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $9.64 to $9.88. 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.

F3 · 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: 0001840776-25-000180 · wk-form4_1750278110.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,789,071

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F5 · price: This transaction was executed in multiple trades at prices ranging from $9.53 to $9.75. 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.

F3 · 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: 0001840776-25-000180 · wk-form4_1750278110.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,799,451

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F4 · price: This transaction was executed in multiple trades at prices ranging from $9.47 to $9.67. 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.

F3 · 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: 0001840776-25-000180 · wk-form4_1750278110.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 3,804,061

F1 · kind: The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 9, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $9.43 to $9.64. 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.

F3 · 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.