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

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

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

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

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.

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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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.

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.

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.

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

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.

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.

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.

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.

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.

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

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.

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.

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.

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.

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.

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.

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

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.

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.

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.

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.

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.

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.

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

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.

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.