HGTY

SEC source: 0001628280-26-003646 · wk-form4_1769549934.xml · nonDerivative · entry 1

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 50,000

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: 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.

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.

SEC source: 0001628280-26-003095 · wk-form4_1769116883.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: 825,213

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 825,213 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 825,213 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 825,213 Released Units.

SEC source: 0001628280-26-003095 · wk-form4_1769116883.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 $12.38 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.

SEC source: 0001628280-26-003095 · wk-form4_1769116883.xml · nonDerivative · entry 1

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 50,000

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: 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 825,213 Released Units.

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.

SEC source: 0001628280-26-001989 · wk-form4_1768343230.xml · derivative · entry 7

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 875,213

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 1,350 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 925,213 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 1,350 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 925,213 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 1,350 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 925,213 Released Units.

SEC source: 0001628280-26-001989 · wk-form4_1768343230.xml · nonDerivative · entry 4

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.

F6 · price: This transaction was executed in multiple trades at prices ranging from $12.63 to $12.99. 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.

SEC source: 0001628280-26-001989 · wk-form4_1768343230.xml · nonDerivative · entry 3

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 50,000

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.

F5 · 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 875,213 Released Units.

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.

SEC source: 0001628280-26-001989 · wk-form4_1768343230.xml · derivative · entry 6

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 925,213

Underlying: Class A Common Stock · 1,350 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 1,350 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 925,213 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 1,350 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 925,213 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 1,350 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 925,213 Released Units.

SEC source: 0001628280-26-001989 · wk-form4_1768343230.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 $13.25 to $13.26. 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.

SEC source: 0001628280-26-001989 · wk-form4_1768343230.xml · nonDerivative · entry 1

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 1,350

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: 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 1,350 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 925,213 Released Units.

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.

SEC source: 0001628280-26-001224 · wk-form4_1767823501.xml · derivative · entry 10

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 926,563

Underlying: Class A Common Stock · 24,247 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 164,870 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 961,693 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 164,870 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 961,693 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 164,870 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 961,693 Released Units.

SEC source: 0001628280-26-001224 · wk-form4_1767823501.xml · nonDerivative · entry 6

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.

F8 · price: This transaction was executed in multiple trades at prices ranging from $13.00 to $13.17. 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.

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.

SEC source: 0001628280-26-001224 · wk-form4_1767823501.xml · nonDerivative · entry 5

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 24,247

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.

F7 · 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 24,247 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 926,563 Released Units.

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.

SEC source: 0001628280-26-001224 · wk-form4_1767823501.xml · derivative · entry 9

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 950,810

Underlying: Class A Common Stock · 10,883 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 164,870 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 961,693 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 164,870 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 961,693 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 164,870 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 961,693 Released Units.

SEC source: 0001628280-26-001224 · wk-form4_1767823501.xml · nonDerivative · entry 4

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.

F6 · price: This transaction was executed in multiple trades at prices ranging from $12.75 to $12.96. 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.

SEC source: 0001628280-26-001224 · wk-form4_1767823501.xml · nonDerivative · entry 3

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 10,883

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.

F5 · 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 10,883 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 950,810 Released Units.

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.

SEC source: 0001628280-26-001224 · wk-form4_1767823501.xml · derivative · entry 8

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 961,693

Underlying: Class A Common Stock · 164,870 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 164,870 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 961,693 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 164,870 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 961,693 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 164,870 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 961,693 Released Units.

SEC source: 0001628280-26-001224 · wk-form4_1767823501.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 $12.57 to $13.12. 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.

SEC source: 0001628280-26-001224 · wk-form4_1767823501.xml · nonDerivative · entry 1

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 164,870

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: 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 164,870 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 961,693 Released Units.

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.

SEC source: 0001628280-25-059032 · wk-form4_1767045821.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 748,097

F1 · kind: Bona fide gift of 150,000 shares to a donor-advised fund sponsored by RK Family DAF for which no consideration was received.

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

SEC source: 0001628280-25-057650 · wk-form4_1766006292.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: 1,126,563

Underlying: Class A Common Stock · 100,000 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 100,000 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 1,126,563 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 100,000 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 1,126,563 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 100,000 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 1,126,563 Released Units.

SEC source: 0001628280-25-057650 · wk-form4_1766006292.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 $12.58 to $12.99. 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.

SEC source: 0001628280-25-057650 · wk-form4_1766006292.xml · nonDerivative · entry 1

Ahn Kenneth · CIK 0001852587 · President, Hagerty Marketplace

10b5-1 filing: Plan reported

Ownership: Indirect · By Quadrifoglio Holdings LLC

Disclosed balance after: 100,000

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: 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 100,000 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 1,126,563 Released Units.

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.

SEC source: 0001628280-25-046783 · wk-form4_1761683128.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 898,097

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 $10.97 to $11.22. 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: 0001628280-25-046289 · wk-form4_1761338994.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 913,367

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 $11.03 to $11.30. 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: 0001628280-25-046289 · wk-form4_1761338994.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 928,098

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 $11.04 to $11.34. 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: 0001628280-25-046289 · wk-form4_1761338994.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 943,098

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 $11.33. 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: 0001628280-25-045726 · wk-form4_1761079824.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 952,593

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 $11.03 to $11.29. 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: 0001628280-25-045726 · wk-form4_1761079824.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 964,812

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 $11.12 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: 0001628280-25-045726 · wk-form4_1761079824.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 973,098

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 $11.21 to $11.51. 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: 0001628280-25-045232 · wk-form4_1760648264.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 987,742

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 $11.39 to $12.30. 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: 0001628280-25-045232 · wk-form4_1760648264.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,011,134

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 $12.04 to $12.33. 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: 0001628280-25-045232 · wk-form4_1760648264.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,023,525

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 $11.86 to $12.26. 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: 0001628280-25-044694 · wk-form4_1760042510.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,079,049

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 $11.71 to $12.13. 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: 0001628280-25-044694 · wk-form4_1760042510.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,101,678

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 $11.84 to $12.02. 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: 0001628280-25-044327 · wk-form4_1759783410.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,108,539

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 $11.94 to $12.09. 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: 0001628280-25-044058 · wk-form4_1759522763.xml · nonDerivative · entry 2

McClymont Patrick · CIK 0001589119 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 314,207

F2 · shares: Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of April 1, 2025 through September 30, 2025.

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, 2025.

SEC source: 0001628280-25-044047 · wk-form4_1759522609.xml · nonDerivative · entry 2

Chafey Diana · CIK 0001867966 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 56,934

F2 · shares: Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of April 1, 2025 through September 30, 2025.

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, 2025.

SEC source: 0001628280-25-044327 · wk-form4_1759783410.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,111,563

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 $11.75 to $12.18. 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: 0001628280-25-043464 · wk-form4_1759351358.xml · nonDerivative · entry 3

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,132,877

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 $11.87 to $12.46. 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.

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: 0001628280-25-044068 · wk-form4_1759522860.xml · nonDerivative · entry 1

Page Russell Andrew · CIK 0002020291 · Chief Information Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 112,024

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, 2022.

SEC source: 0001628280-25-044045 · wk-form4_1759522530.xml · nonDerivative · entry 1

DELANEY KEVIN M · CIK 0001398794 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 90,797

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 October 1, 2028, 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: 0001628280-25-044058 · wk-form4_1759522763.xml · nonDerivative · entry 1

McClymont Patrick · CIK 0001589119 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 313,746

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, 2022.

SEC source: 0001628280-25-044047 · wk-form4_1759522609.xml · nonDerivative · entry 1

Chafey Diana · CIK 0001867966 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 55,941

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: 0001628280-25-043464 · wk-form4_1759351358.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,151,249

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 $11.63 to $12.05. 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: 0001628280-25-043464 · wk-form4_1759351358.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,181,436

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 $11.69 to $12.01. 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: 0001628280-25-042597 · wk-form4_1758745620.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,186,942

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 $12.24 to $12.54. 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: 0001124462-25-000025 · wk-form4_1758140737.xml · nonDerivative · entry 2

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,221,389

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 $12.36 to $12.66. 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: 0001124462-25-000025 · wk-form4_1758140737.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,239,011

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 $12.64 to $12.91. 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: 0001124462-25-000017 · wk-form4_1757365150.xml · nonDerivative · entry 1

KAUFFMAN ROBERT I · CIK 0001124462 · Director

10b5-1 filing: Plan reported

Ownership: Indirect · By Aldel LLC

Disclosed balance after: 1,250,444

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 $11.91 to $12.09. 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.