HG · Hamilton Insurance Group, Ltd. · Insider Trading

The price reported in Column 4 represents a weighted average price. These Class B common shares were sold in multiple transactions at prices ranging from $34.47 to $35.33, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

Includes restricted stock units.

The price reported in Column 4 represents a weighted average price. These Class B common shares were sold in multiple transactions at prices ranging from $34.50 to $34.565, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

Includes restricted stock units.

The price reported in Column 4 represents a weighted average price. These Class B common shares were sold in multiple transactions at prices ranging from $36.00 to $36.47, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

An investment holding company held by Thelwall Trust, a family trust established for the benefit of the reporting person and his family.

Represents a gift by the reporting person of 100,430 Class B common shares to the Pina Albo 2018 Long Term Trust for no consideration. Following this gift, the reporting person disclaims beneficial ownership of the shares held by such trust.

Includes restricted stock units.

Represents a gift by the reporting person of 100,430 Class B common shares to the reporting person's spouse for no consideration. Following the gift, the reporting person may be deemed to beneficially own such shares indirectly through her spouse.

Represents a gift by the reporting person of 100,430 Class B common shares to the reporting person's spouse for no consideration. Following the gift, the reporting person may be deemed to beneficially own such shares indirectly through her spouse.

Includes restricted stock units.

Represents a subsequent gift by the reporting person's spouse of 100,430 Class B common shares to the Kim Hertel 2018 Long Term Trust for no consideration. Following this gift, the reporting person disclaims beneficial ownership of the shares held by such trust.

The price reported in Column 4 represents a weighted average price. These Class B common shares were sold in multiple transactions at prices ranging from $32.00 to $32.41, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

An investment holding company held by Thelwall Trust, a family trust established for the benefit of the reporting person and his family.

The price reported in Column 4 represents a weighted average price. These Class B common shares were sold in multiple transactions at prices ranging from $31.52 to $32.09, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

An investment holding company held by Thelwall Trust, a family trust established for the benefit of the reporting person and his family.

Includes restricted stock units.

Includes restricted stock units.

Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on May 5, 2026, which was $30.43 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

Includes restricted stock units.

Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on May 5, 2026, which was $30.43 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

Includes restricted stock units.

The price reported in Column 4 represents a weighted average price. These Class B common shares were sold in multiple transactions at prices ranging from $30.57 to $30.92, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

Includes restricted stock units.

Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on May 5, 2026, which was $30.43 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

Includes restricted stock units.

Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on May 5, 2026, which was $30.43 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

Includes restricted stock units.

Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on May 5, 2026, which was $30.43 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

Includes restricted stock units.

Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on May 5, 2026, which was $30.43 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

Includes restricted stock units.

Represents shares withheld to satisfy tax obligations arising out of the vesting of the reporting person's restricted stock units.

Represents the closing price per share on May 5, 2026, used to determine the number of shares to be withheld by the issuer to satisfy tax withholding obligations.

Includes restricted stock units.

Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on May 5, 2026, which was $30.43 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

Includes restricted stock units.

Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on May 5, 2026, which was $30.43 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

Includes restricted stock units.

Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on May 5, 2026, which was $30.43 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

Includes restricted stock units.

Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on May 5, 2026, which was $30.43 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

Includes restricted stock units.

Represents a grant of restricted stock units ("RSUs") pursuant to the Hamilton Insurance Group, Ltd. Equity Incentive Plan. Each RSU represents a contingent right to receive one share of Class B common shares upon vesting. The RSUs vest in three equal annual installments beginning on March 1, 2027, subject to the reporting person's continued service through each vesting date.

Includes restricted stock units.

Represents shares withheld to satisfy tax obligations arising out of the vesting of the reporting person's restricted stock units.

Represents the closing price per share on February 27, 2025, used to determine the number of shares to be withheld by the issuer to satisfy tax withholding obligations.

Includes restricted stock units.

Represents a grant of restricted stock units ("RSUs") pursuant to the Hamilton Insurance Group, Ltd. Equity Incentive Plan. Each RSU represents a contingent right to receive one share of Class B common shares upon vesting. The RSUs vest in three equal annual installments beginning on March 1, 2027, subject to the reporting person's continued service through each vesting date.

Includes restricted stock units.

Represents a grant of restricted stock units ("RSUs") pursuant to the Hamilton Insurance Group, Ltd. Equity Incentive Plan. Each RSU represents a contingent right to receive one share of Class B common shares upon vesting. The RSUs vest in three equal annual installments beginning on March 1, 2027, subject to the reporting person's continued service through each vesting date.

Includes restricted stock units.

Represents a grant of restricted stock units ("RSUs") pursuant to the Hamilton Insurance Group, Ltd. Equity Incentive Plan. Each RSU represents a contingent right to receive one share of Class B common shares upon vesting. The RSUs vest in three equal annual installments beginning on March 1, 2027, subject to the reporting person's continued service through each vesting date.

Includes restricted stock units.

Represents a grant of restricted stock units ("RSUs") pursuant to the Hamilton Insurance Group, Ltd. Equity Incentive Plan. Each RSU represents a contingent right to receive one share of Class B common shares upon vesting. The RSUs vest in three equal annual installments beginning on March 1, 2027, subject to the reporting person's continued service through each vesting date.

Includes restricted stock units.

Represents a grant of restricted stock units ("RSUs") pursuant to the Hamilton Insurance Group, Ltd. Equity Incentive Plan. Each RSU represents a contingent right to receive one share of Class B common shares upon vesting. The RSUs vest in three equal annual installments beginning on March 1, 2027, subject to the reporting person's continued service through each vesting date.

Reflects RSUs.

Represents a grant of restricted stock units ("RSUs") pursuant to the Hamilton Insurance Group, Ltd. Equity Incentive Plan. Each RSU represents a contingent right to receive one share of Class B common shares upon vesting. The RSUs vest in three equal annual installments beginning on March 1, 2027, subject to the reporting person's continued service through each vesting date.

Includes restricted stock units.

Represents shares withheld to satisfy tax obligations arising out of the vesting of the reporting person's restricted stock units.

Represents the closing price per share on February 27, 2025, used to determine the number of shares to be withheld by the issuer to satisfy tax withholding obligations.

Includes restricted stock units.

Represents a grant of restricted stock units ("RSUs") pursuant to the Hamilton Insurance Group, Ltd. Equity Incentive Plan. Each RSU represents a contingent right to receive one share of Class B common shares upon vesting. The RSUs vest in three equal annual installments beginning on March 1, 2027, subject to the reporting person's continued service through each vesting date.

Includes restricted stock units.

Represents a grant of restricted stock units ("RSUs") pursuant to the Hamilton Insurance Group, Ltd. Equity Incentive Plan. Each RSU represents a contingent right to receive one share of Class B common shares upon vesting. The RSUs vest in three equal annual installments beginning on March 1, 2027, subject to the reporting person's continued service through each vesting date.

Reflects RSUs.

Represents shares withheld to satisfy tax obligations arising out of the vesting of the reporting person's restricted stock units.

Represents the closing price per share on February 27, 2025, used to determine the number of shares to be withheld by the issuer to satisfy tax withholding obligations.

Includes restricted stock units.

Represents a grant of restricted stock units ("RSUs") pursuant to the Hamilton Insurance Group, Ltd. Equity Incentive Plan. Each RSU represents a contingent right to receive one share of Class B common shares upon vesting. The RSUs vest in three equal annual installments beginning on March 1, 2027, subject to the reporting person's continued service through each vesting date.

Includes restricted stock units.

This Form 4/A amends the Form 4 originally filed on March 4, 2026, to correct the number of shares withheld to satisfy tax obligations and the number of shares of common stock beneficially owned following the reported transaction. Due to an adjustment in the tax withholding calculation, the original filing understated the reporting person's post-transaction holdings by 61 shares. The corrected amounts are reflected herein.

Represents the closing price per share on February 27, 2026, used to determine the number of shares to be withheld by the issuer to satisfy tax withholding obligations.

Includes restricted stock units.

Represents a grant of restricted stock units ("RSUs") pursuant to the Hamilton Insurance Group, Ltd. Equity Incentive Plan. Each RSU represents a contingent right to receive one share of Class B common shares upon vesting. The RSUs vest in three equal annual installments beginning on March 1, 2027, subject to the reporting person's continued service through each vesting date.

Includes restricted stock units.

Total reflects rounding adjustments and has been updated accordingly.

Represents shares withheld to satisfy tax obligations arising out of the vesting of the reporting person's restricted stock units.

Represents the closing price per share on February 27, 2025, used to determine the number of shares to be withheld by the issuer to satisfy tax withholding obligations.

Includes restricted stock units.

Represents shares acquired upon the certification by Hamilton Insurance Group, Ltd. ("HG") for the satisfaction of performance criteria underlying an award of performance stock units ("PSUs") previously granted to the reporting person under the terms of the HG Equity Incentive Plan. The reporting person's PSUs are earned based on the HG annualized underwriting return on capital for the 3-year performance period ending on December 31, 2025. HG confirmed the annualized underwriting return on capital for the 3-year performance period ending on December 31, 2025, was 8.6%, resulting in a performance payout at 200% of target.

Includes restricted stock units.

Represents shares withheld to satisfy tax obligations arising out of the vesting of the reporting person's PSUs.

Represents the closing price per share on February 24, 2025, used to determine the number of shares to be withheld by the issuer to satisfy tax withholding obligations.

Includes restricted stock units.

Represents shares acquired upon the certification by Hamilton Insurance Group, Ltd. ("HG") for the satisfaction of performance criteria underlying an award of performance stock units ("PSUs") previously granted to the reporting person under the terms of the HG Equity Incentive Plan. The reporting person's PSUs are earned based on the HG annualized underwriting return on capital for the 3-year performance period ending on December 31, 2025. HG confirmed the annualized underwriting return on capital for the 3-year performance period ending on December 31, 2025, was 8.6%, resulting in a performance payout at 200% of target.

Includes restricted stock units.

Represents shares acquired upon the certification by Hamilton Insurance Group, Ltd. ("HG") for the satisfaction of performance criteria underlying an award of performance stock units ("PSUs") previously granted to the reporting person under the terms of the HG Equity Incentive Plan. The reporting person's PSUs are earned based on the HG annualized underwriting return on capital for the 3-year performance period ending on December 31, 2025. HG confirmed the annualized underwriting return on capital for the 3-year performance period ending on December 31, 2025, was 8.6%, resulting in a performance payout at 200% of target.

Includes restricted stock units.

Represents shares acquired upon the certification by Hamilton Insurance Group, Ltd. ("HG") for the satisfaction of performance criteria underlying an award of performance stock units ("PSUs") previously granted to the reporting person under the terms of the HG Equity Incentive Plan. The reporting person's PSUs are earned based on the HG annualized underwriting return on capital for the 3-year performance period ending on December 31, 2025. HG confirmed the annualized underwriting return on capital for the 3-year performance period ending on December 31, 2025, was 8.6%, resulting in a performance payout at 200% of target.

Includes restricted stock units.

Represents shares withheld to satisfy tax obligations arising out of the vesting of the reporting person's PSUs.

Represents the closing price per share on February 24, 2025, used to determine the number of shares to be withheld by the issuer to satisfy tax withholding obligations.

Includes restricted stock units.

Represents shares withheld to satisfy tax obligations arising out of the vesting of the reporting person's PSUs.

Represents the closing price per share on February 24, 2025, used to determine the number of shares to be withheld by the issuer to satisfy tax withholding obligations.

Includes restricted stock units.

Represents shares withheld to satisfy tax obligations arising out of the vesting of the reporting person's PSUs.

Represents the closing price per share on February 24, 2026, used to determine the number of shares to be withheld by the issuer to satisfy tax withholding obligations.

Includes restricted stock units.