[Form 4] Hamilton Insurance Group, Ltd. Insider Trading Activity

Rhea-AI Filing Summary

Hamilton Insurance Group director Karen Ann Green reported routine equity compensation activity involving Class B Common Shares. She received an annual grant of 4,929 restricted stock units valued at $150,000, based on the closing share price of $30.43 on May 5, 2026, under the company’s Non-Employee Director Compensation Program.

On the same date, 3,378 shares were withheld at $30.43 per share to cover tax obligations arising from the vesting of her restricted stock units, rather than being sold in the open market. Following these transactions, she directly holds 12,116 shares, including restricted stock units, reflecting a net increase in her reported holdings.

Insider Trade Summary

2 transactions reported

Mixed 2 txns

Insider Green Karen Ann

Role null

Type	Security	Shares	Price	Value
Grant/Award	Class B Common Shares	4,929	$0.00	--
Tax Withholding	Class B Common Shares	3,378	$30.43	$103K

Holdings After Transaction: Class B Common Shares — 12,116 shares (Direct, null)

Footnotes (1)

1. 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.

Key Figures

RSU grant value: $150,000 RSUs granted: 4,929 shares Tax withholding shares: 3,378 shares +2 more

5 metrics

RSU grant value $150,000 Target grant value for annual director RSU award on May 5, 2026

RSUs granted 4,929 shares Restricted stock units based on $30.43 May 5, 2026 closing price

Tax withholding shares 3,378 shares Shares withheld to satisfy tax obligations on RSU vesting

Reference share price $30.43 per share Closing price on May 5, 2026 used for grant and withholding

Post-transaction holdings 12,116 shares Director’s direct holdings after transactions, including RSUs

Key Terms

restricted stock units ("RSUs"), Non-Employee Director Compensation Program, cliff vest, tax withholding obligations

4 terms

restricted stock units ("RSUs") financial

"Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person"

Restricted stock units (RSUs) are a company promise to give an employee shares of stock (or cash equivalent) in the future, but only after certain conditions—usually staying with the company for a set time or hitting performance goals—are met. Investors watch RSUs because when they vest they increase the number of shares outstanding and can lead insiders to sell shares, affecting share price, company dilution and the true cost of employee pay.

Non-Employee Director Compensation Program financial

"awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program"

cliff vest financial

"The RSUs cliff vest on the earlier of the one-year anniversary of the grant date"

A cliff vest is a schedule for stock options or restricted shares where no ownership rights are earned until a fixed date, after which a set portion becomes fully owned all at once — like a probation period that suddenly unlocks pay. Investors watch cliff vests because they influence when insiders can sell shares, affect staff retention and dilution timing, and help predict short-term changes in a company’s shareholder makeup.

tax withholding obligations financial

"used to determine the number of shares to be withheld by the issuer to satisfy tax withholding obligations"

Form 4 Insider Transactions: What Each Field Means →

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Green Karen Ann

(Last) (First) (Middle)

C/O HAMILTON INSURANCE GROUP, LTD.

WELLESLEY HOUSE NORTH, 90 PITTS BAY ROAD

(Street)

PEMBROKE HM 08

(City) (State) (Zip)

BERMUDA

(Country)

2. Issuer Name and Ticker or Trading Symbol
Hamilton Insurance Group, Ltd. [ HG ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
	Officer (give title below)		Other (specify below)

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/05/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Class B Common Shares	05/05/2026		A		4,929(1)	A	$0	12,116(2)	D
Class B Common Shares	05/05/2026		F		3,378(3)	D	$30.43(4)	8,738(2)	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. 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.

2. Includes restricted stock units.

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

4. 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.

Remarks:

	/s/ By Ryan Minett, Attorney-in-Fact	05/07/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)