How did Hamilton (HG)'s book value per share change in 2026?

At June 30, 2026, book value per common share was $28.91 , and book value per share plus accumulated dividends was $30.91 , an 8.5% increase from $28.50 at December 31, 2025, despite paying a substantial special dividend.

Hamilton Insurance Group (NYSE: HG) Q2 profit $143.8M with 16.7% premium growth

Q: What were Hamilton Insurance Group (HG)'s key Q2 2026 earnings results?

Hamilton reported Q2 2026 net income of $143.8 million , or $1.42 per diluted share, with an annualized return on average common equity of 20.6% . Operating income was $158.2 million , or $1.56 per diluted share, and total revenues reached $839.6 million.

Q: How did Hamilton (HG)'s underwriting performance change in 2026?

For Q2 2026, Hamilton’s combined ratio was 95.0% , up from 86.8% a year earlier, with underwriting income of $29.1 million . Year to date, the combined ratio improved to 92.5% from 99.1%, and underwriting income increased to $86.7 million from $9.2 million.

Q: What premium growth did Hamilton (HG) report in Q2 2026?

Gross premiums written grew 16.7% to $831.0 million in Q2 2026. The International segment increased premiums by 21.8% to $420.1 million, while the Bermuda segment grew 11.9% to $411.0 million, reflecting expansion in casualty and specialty lines.

Q: How did Hamilton (HG)'s investments perform year to date in 2026?

Year to date, Hamilton generated $234.9 million of net investment income, including $208.5 million from the Two Sigma Hamilton Fund and $26.4 million from fixed income, short-term and cash investments. Total cash and invested assets were $6.1 billion at June 30, 2026.

Q: What capital management actions did Hamilton (HG) take in 2026?

On February 18, 2026, Hamilton’s board declared a $2.00 per share special dividend totaling $205.8 million , paid March 30, 2026. The company also repurchased $22.1 million of common shares in Q2 and $41.8 million year to date.

Filing Impact

(High)

Filing Sentiment

(Neutral)

Form Type

8-K

Rhea-AI Filing Summary

Hamilton Insurance Group, Ltd. reported strong profitability for the quarter ended June 30, 2026, with net income of $143.8 million, or $1.42 per diluted share, and an annualized return on average common equity of 20.6%. Operating income was $158.2 million, or $1.56 per diluted share, with an annualized operating ROE of 22.7%. Gross premiums written grew 16.7% to $831.0 million and net premiums earned rose 14.6% to $586.0 million. Higher catastrophe and prior‑year losses, including $49.9 million largely from the Middle East conflict and unfavorable development, lifted the loss ratio to 61.7% and the combined ratio to 95.0% from 86.8% in the prior‑year quarter.

For the first six months of 2026, Hamilton generated net income of $277.3 million and operating income of $324.9 million. The year‑to‑date combined ratio improved to 92.5% from 99.1%, and underwriting income increased to $86.7 million from $9.2 million, supported by $234.9 million of net investment income, including significant contributions from the Two Sigma Hamilton Fund. Book value per common share was $28.91, and book value per share plus accumulated dividends reached $30.91, up 8.5% since December 31, 2025. Capital management actions included a $2.00 per share special dividend and $41.8 million of share repurchases year to date.

Hamilton’s board approved an amendment to Chief Executive Officer Pina Albo’s employment agreement, extending her term through December 31, 2029, with automatic one‑year renewals thereafter, reinforcing leadership continuity as the company pursues its long‑term strategy.

Positive

Year-to-date underwriting performance strengthened, with the combined ratio improving to 92.5% from 99.1% and underwriting income rising to $86.7 million from $9.2 million in the prior-year period.
Net investment income reached $234.9 million year to date, including $208.5 million from the Two Sigma Hamilton Fund, supporting robust operating income of $324.9 million.
Book value per common share plus accumulated dividends increased 8.5% to $30.91 since December 31, 2025, after paying a $2.00 per share special dividend and repurchasing $41.8 million of common shares in 2026.

Negative

Quarterly underwriting income declined to $29.1 million from $67.5 million as the combined ratio worsened to 95.0% from 86.8% in the second quarter of 2025.
Catastrophe and prior-year losses, primarily from the Middle East conflict and related development, totaled $49.9 million, contributing to higher loss ratios in 2026.

Filing Explained

On August 6, 2026, Hamilton Insurance Group reported that it had entered into the CEO employment-agreement amendment, extending Giuseppina C. Albo’s term through December 31, 2029, with automatic one-year renewals thereafter unless terminated under the agreement.

8-K Event Classification

3 items: 2.02, 5.02, 9.01

3 items

Item 2.02 Results of Operations and Financial Condition Financial

Disclosure of earnings results, typically an earnings press release or preliminary financials.

Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers Governance

Key personnel changes including departures, elections, or appointments of directors and executive officers.

Item 9.01 Financial Statements and Exhibits Exhibits

Financial statements, pro forma financial information, and exhibit attachments filed with this report.

Key Figures

Q2 2026 net income: $143.8 million Q2 2026 diluted EPS: $1.42 Q2 2026 combined ratio: 95.0% +4 more

7 metrics

Q2 2026 net income $143.8 million Net income attributable to common shareholders for the quarter ended June 30, 2026

Q2 2026 diluted EPS $1.42 Income per share attributable to common shareholders – diluted, second quarter 2026

Q2 2026 combined ratio 95.0% Consolidated combined ratio for the quarter ended June 30, 2026

YTD 2026 combined ratio 92.5% Combined ratio for the six months ended June 30, 2026, versus 99.1% in 2025

YTD 2026 underwriting income $86.7 million Underwriting income for the six months ended June 30, 2026

Book value per common share plus accumulated dividends $30.91 At June 30, 2026, up 8.5% from $28.50 at December 31, 2025

Special dividend per share $2.00 Special dividend declared February 18, 2026, totaling $205.8 million

Key Terms

Combined ratio, Attritional loss ratio, Catastrophe loss ratio, Operating income attributable to common shareholders, +1 more

5 terms

Combined ratio financial

"Combined ratio is a measure of our underwriting profitability and is expressed as the sum of the loss and loss adjustment expense ratio"

The combined ratio is a way insurance companies measure how well they are doing by adding up all their costs and claims and comparing them to the money they earn from premiums. If the ratio is below 100%, it means the company is making a profit; if it's above 100%, they are losing money. It helps see if an insurance company is financially healthy or not.

Attritional loss ratio financial

"Attritional loss ratio – current year is the attritional losses incurred by the company relating to the current year divided by net premiums earned"

The attritional loss ratio measures the share of an insurer’s regular, small-to-moderate claims—think routine repairs and medical bills—compared with the premiums earned to cover them. Investors use it to judge the predictable part of an insurer’s costs; a rising attritional loss ratio signals weaker underlying profitability or underpriced products, while a stable low ratio suggests steady, manageable claims and more reliable earnings.

Catastrophe loss ratio financial

"Catastrophe loss ratio – current year is the catastrophe losses incurred by the company relating to the current year divided by net premiums earned"

The catastrophe loss ratio measures the portion of an insurer’s collected premiums that is paid out to cover claims from major disasters, like storms, earthquakes or large-scale accidents. It matters to investors because a high ratio is like a household draining its savings after an unexpected storm: it can squeeze profits, force the company to raise prices or tap capital, and reveal whether disaster coverage is priced and managed sustainably.

Operating income attributable to common shareholders financial

"Operating income (loss) attributable to common shareholders, as used herein, differs from net income by the exclusion of net realized and unrealized gains and losses"

Earnings Snapshot

Q2 2026 net income attributable to common shareholders: $143.8 million

quarter and six months ended June 30, 2026

Q2 2026 net income attributable to common shareholders $143.8 million down from $187.4 million in Q2 2025

Q2 2026 diluted EPS $1.42 down from $1.79 in Q2 2025

Q2 2026 combined ratio 95.0% up from 86.8% in Q2 2025

YTD 2026 combined ratio 92.5% improved from 99.1% in the prior-year period

YTD 2026 underwriting income $86.7 million up from $9.2 million in the prior-year period

Book value per common share plus accumulated dividends $30.91 up 8.5% from $28.50 at December 31, 2025

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Understanding 8-K Material Events →

Available on EDGAR 08/06/2026 - 04:20 PM Accepted by SEC EDGAR 08/06/2026 - 04:19 PM

FAQ

What were Hamilton Insurance Group (HG)'s key Q2 2026 earnings results?

Hamilton reported Q2 2026 net income of $143.8 million, or $1.42 per diluted share, with an annualized return on average common equity of 20.6%. Operating income was $158.2 million, or $1.56 per diluted share, and total revenues reached $839.6 million.

How did Hamilton (HG)'s underwriting performance change in 2026?

For Q2 2026, Hamilton’s combined ratio was 95.0%, up from 86.8% a year earlier, with underwriting income of $29.1 million. Year to date, the combined ratio improved to 92.5% from 99.1%, and underwriting income increased to $86.7 million from $9.2 million.

What premium growth did Hamilton (HG) report in Q2 2026?

Gross premiums written grew 16.7% to $831.0 million in Q2 2026. The International segment increased premiums by 21.8% to $420.1 million, while the Bermuda segment grew 11.9% to $411.0 million, reflecting expansion in casualty and specialty lines.

How did Hamilton (HG)'s investments perform year to date in 2026?

Year to date, Hamilton generated $234.9 million of net investment income, including $208.5 million from the Two Sigma Hamilton Fund and $26.4 million from fixed income, short-term and cash investments. Total cash and invested assets were $6.1 billion at June 30, 2026.

What capital management actions did Hamilton (HG) take in 2026?

On February 18, 2026, Hamilton’s board declared a $2.00 per share special dividend totaling $205.8 million, paid March 30, 2026. The company also repurchased $22.1 million of common shares in Q2 and $41.8 million year to date.

What leadership update did Hamilton Insurance Group (HG) announce?

Hamilton amended CEO Pina Albo’s employment agreement to extend her term through December 31, 2029, after which it will automatically renew for successive one‑year periods unless terminated under the agreement’s terms, signaling the board’s confidence in her ongoing leadership.

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

___________________________________

FORM 8-K

___________________________________

CURRENT REPORT

Pursuant to Section 13 or 15(d)

of the Securities Exchange Act of 1934

August 6, 2026

Date of Report (date of earliest event reported)

___________________________________

Hamilton Insurance Group, Ltd.

(Exact name of registrant as specified in its charter)

___________________________________


Bermuda (State or other jurisdiction of incorporation or organization)	001-41862 (Commission File Number)	98-1153847 (I.R.S. Employer Identification Number)
Wellesley House North, 1st Floor 90 Pitts Bay Road Pembroke, Bermuda HM 08
(Address of principal executive offices and zip code)
(441) 405-5200
(Registrant's telephone number, including area code)

___________________________________

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:


o			Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)
o			Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)
o			Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))
o			Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:

Title of each class

Trading Symbol

Name of each exchange on which

registered

Class B common shares, par value $0.01 per share

New York Stock Exchange

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 12b-2 of the Exchange Act. Emerging growth company o

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. o

Item 2.02 – Results of Operations and Financial Condition

On August 6, 2026, Hamilton Insurance Group, Ltd. (the “Company”) issued a press release announcing its financial results for the quarter ended June 30, 2026 and the availability of its corresponding supplementary financial information. Copies of this press release and the supplementary financial information are furnished as Exhibits 99.1 and 99.2, respectively, to this report. In addition, a copy of our investor presentation which may be referred to during our earnings call is furnished as Exhibit 99.3.

Item 5.02 - Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

On August 6, 2026, the Company entered into the First Amendment to the Second Amended and Restated Employment Agreement with Giuseppina C. Albo, the Company’s Chief Executive Officer (the “Amendment”). The Amendment amends the Second Amended and Restated Employment Agreement, dated September 12, 2023, between the Company and Ms. Albo, to extend Ms. Albo’s employment term through December 31, 2029, after which her employment term will continue to renew automatically for successive one-year periods unless terminated in accordance with the terms of the employment agreement. Except as expressly amended by the Amendment, the employment agreement remains unchanged and in full force and effect.

The foregoing description of the Amendment does not purport to be complete and is qualified in its entirety by reference to the full text of the Amendment, which is filed as Exhibit 10.1 to this Current Report on Form 8-K and is incorporated by reference herein.

Item 9.01 - Financial Statements and Exhibits

(d):The following exhibits are being filed or furnished herewith, as applicable:


Exhibit No.						Description
10.1						First Amendment to Second Amended and Restated Employment Agreement, dated August 6, 2026, between Hamilton Insurance Group, Ltd. and Giuseppina C. Albo.
99.1						Press Release, dated August 6, 2026, issued by Hamilton Insurance Group, Ltd.
99.2						Supplementary Financial Information - June 30, 2026
99.3						Investor Presentation - June 30, 2026
104						Cover Page Interactive Data File (embedded within the Inline XBRL document)

SIGNATURE

Pursuant to the requirements of the Securities Exchange Act of 1934, as amended, the Registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

Date: August 6, 2026.


			HAMILTON INSURANCE GROUP, LTD.

			By:			/s/ Brian Deegan
			Name:			Brian Deegan
			Title:			Group Chief Accounting Officer

Hamilton Reports 2026 Second Quarter Results

Net Income of $144 million; Annualized Return on Average Equity of 21%

Operating Income of $158 million; Annualized Operating Return on Average Equity of 23%

PEMBROKE, Bermuda, August 6, 2026 – Hamilton Insurance Group, Ltd. (NYSE: HG; “Hamilton” or the “Company”) today announced financial results for the second quarter ended June 30, 2026.

Commenting on the results, Pina Albo, CEO of Hamilton, said:

“Hamilton delivered another quarter of strong results, with net income of $144 million, a 21% annualized return on average equity, a 95% combined ratio, and strong investment income. Gross premiums written increased 17%, reflecting our continued focus on margin quality, thoughtful risk selection, and long-term value creation.

I am proud of our team’s continued execution as we navigate a market that requires and rewards strong broker and client relationships and disciplined underwriting.”

Leadership Update

The Board of Directors of Hamilton are delighted to announce an amendment to the employment agreement of its Chief Executive Officer, Pina Albo, extending her employment term through December 31, 2029, after which her employment term will continue to renew automatically for successive one-year periods. David A. Brown, Chairman of Hamilton's Board of Directors, said: "Under Pina's leadership, Hamilton has built a differentiated platform and delivered strong performance. Extending her employment term reflects the Board's confidence in her exceptional leadership and our commitment to executing the Company's long-term strategy for the benefit of our shareholders.”

Consolidated Highlights – Second Quarter

•Net income of $143.8 million, or $1.42 per diluted share and operating income of $158.2 million, or $1.56 per diluted share;

•Annualized return on average equity of 20.6% and annualized operating return on average equity of 22.7%;

•Gross premiums written of $831.0 million, an increase of 16.7% compared to the second quarter of 2025;

•Net premiums earned of $586.0 million, an increase of 14.6% compared to the second quarter of 2025;

•Combined ratio of 95.0%;

•Underwriting income of $29.1 million;

•Net investment income of $141.3 million, comprised of Two Sigma Hamilton Fund returns of $115.5 million, and fixed income, short term and cash and cash equivalents returns of $25.8 million; and

•Repurchased common shares of $22.1 million in the second quarter of 2026.

Consolidated Highlights – Year to Date

•Net income of $277.3 million, or $2.73 per diluted share and operating income of $324.9 million, or $3.20 per diluted share;

•Annualized return on average equity of 19.6% and annualized operating return on average equity of 22.9%;

•Gross premiums written of $1.8 billion, an increase of 13.9% compared to the same period in 2025;

•Net premiums earned of $1.2 billion, an increase of 14.5% compared to the same period in 2025;

•Combined ratio of 92.5%;

•Underwriting income of $86.7 million;

•Net investment income of $234.9 million, comprised of Two Sigma Hamilton Fund returns of $208.5 million, and fixed income, short term and cash and cash equivalents returns of $26.4 million;

•On February 18, 2026, the Company’s Board of Directors declared a special dividend of $2.00 per share, or $205.8 million. The dividend was paid on March 30, 2026, to common shareholders of record as of March 6, 2026;

•Book value per share of $28.91, an increase of 1.4% compared to December 31, 2025;

•Book value per common share plus accumulated dividends of $30.91, an increase of 8.5% compared to December 31, 2025; and

•Repurchased common shares of $41.8 million in 2026.

Consolidated Results – Second Quarter


	For the Three Months Ended
($ in thousands, except for per share amounts and percentages)	June 30, 2026		June 30, 2025		Change
Gross premiums written	$	831,041	$	712,026	$	119,015
Net premiums written	621,695		556,314		65,381
Net premiums earned	586,007		511,163		74,844
Underwriting income (loss)	$	29,112	$	67,459	$	(38,347)
Combined ratio	95.0%		86.8%		8.2 pts

Net income (loss) attributable to common shareholders	$	143,782	$	187,415	$	(43,633)
Income (loss) per share attributable to common shareholders - diluted	$	1.42	$	1.79


Book value per common share	$	28.91	$	25.55

Accumulated dividends	$	2.00	$	—
Book value per common share plus accumulated dividends	$	30.91	$	25.55


Return on average common equity - annualized	20.6%		30.2%


	For the Three Months Ended
Key Ratios	June 30, 2026		June 30, 2025		Change
Attritional loss ratio - current year	53.3	%	53.0	%	0.3	pts
Attritional loss ratio - prior year	(0.1	%)	(0.5	%)	0.4	pts
Catastrophe loss ratio - current year	7.8	%	1.9	%	5.9	pts
Catastrophe loss ratio - prior year	0.7	%	(1.6	%)	2.3	pts
Loss and loss adjustment expense ratio	61.7	%	52.8	%	8.9	pts
Acquisition cost ratio	24.8	%	24.0	%	0.8	pts
Other underwriting expense ratio	8.5	%	10.0	%	(1.5	pts)
Combined ratio	95.0	%	86.8	%	8.2	pts

•Gross premiums written increased by $119.0 million, or 16.7%, to $831.0 million with an increase of $75.3 million, or 21.8%, in the International Segment, and $43.7 million, or 11.9%, in the Bermuda Segment.

•Net premiums written increased by $65.4 million, or 11.8%, to $621.7 million with an increase of $64.8 million, or 25.1%, in the International Segment, and an increase of $0.6 million, or 0.2%, in the Bermuda Segment.

•Net premiums earned increased by $74.8 million, or 14.6%, to $586.0 million with an increase of $49.4 million, or 19.5%, in the International Segment, and $25.4 million, or 9.9%, in the Bermuda Segment.

•The attritional loss ratio (current year), net of reinsurance, was 53.3%. The increase of 0.3 points was primarily driven by a change in business mix, including an increase in casualty reinsurance business.

•Net favorable attritional prior year reserve development, net of reinsurance, was $0.8 million, primarily driven by favorable development in specialty and property classes, partially offset by unfavorable development in certain casualty classes.

•Catastrophe losses (current and prior year), net of reinsurance, were $49.9 million, primarily driven by the Middle East conflict ($45.7 million) and unfavorable prior year development ($4.2 million).

•The acquisition cost ratio increased by 0.8 points compared to the same period in 2025, primarily driven by a change in business mix.

•The other underwriting expense ratio decreased by 1.5 points compared to the same period in 2025, primarily driven by Bermuda substance-based tax credits and an increase in net premiums earned.

International Segment Underwriting Results – Second Quarter


International Segment	For the Three Months Ended
($ in thousands, except for percentages)	June 30, 2026			June 30, 2025			Change
Gross premiums written	$	420,073		$	344,799		$	75,274
Net premiums written	322,843			258,089			64,754
Net premiums earned	302,623			253,209			49,414
Underwriting income (loss)	$	9,124		$	27,118		$	(17,994)

Key Ratios
Attritional loss ratio - current year	51.1		%	51.9		%	(0.8		pts)
Attritional loss ratio - prior year	(4.6		%)	(3.0		%)	(1.6		pts)
Catastrophe loss ratio - current year	11.1		%	0.6		%	10.5		pts
Catastrophe loss ratio - prior year	0.0		%	(0.2		%)	0.2		pts
Loss and loss adjustment expense ratio	57.6		%	49.3		%	8.3		pts
Acquisition cost ratio	26.5		%	25.9		%	0.6		pts
Other underwriting expense ratio	12.9		%	14.1		%	(1.2		pts)
Combined ratio	97.0		%	89.3		%	7.7		pts

•Gross premiums written increased by $75.3 million, or 21.8%, to $420.1 million, primarily driven by growth in both new and existing business in casualty and specialty insurance classes.

•The attritional loss ratio (current year), net of reinsurance, was 51.1%. The decrease of 0.8 points was primarily driven by the absence of large losses in the current quarter.

•Net favorable attritional prior year reserve development, net of reinsurance, was $13.8 million, primarily driven by favorable development in specialty, property and casualty classes.

•Catastrophe losses (current and prior year), net of reinsurance, were $33.6 million, driven by the Middle East conflict.

•The acquisition cost ratio increased by 0.6 points compared to the same period in 2025, primarily driven by a change in business mix.

•The other underwriting expense ratio decreased by 1.2 points compared to the same period in 2025, primarily driven by growth in the premium base.

Bermuda Segment Underwriting Results – Second Quarter


Bermuda Segment	For the Three Months Ended
($ in thousands, except for percentages)	June 30, 2026			June 30, 2025			Change
Gross premiums written	$	410,968		$	367,227		$	43,741
Net premiums written	298,852			298,225			627
Net premiums earned	283,384			257,954			25,430
Underwriting income (loss)	$	19,988		$	40,341		$	(20,353)

Key Ratios
Attritional loss ratio - current year	55.7		%	54.2		%	1.5		pts
Attritional loss ratio - prior year	4.6		%	2.0		%	2.6		pts
Catastrophe loss ratio - current year	4.3		%	3.2		%	1.1		pts
Catastrophe loss ratio - prior year	1.5		%	(3.1		%)	4.6		pts
Loss and loss adjustment expense ratio	66.1		%	56.3		%	9.8		pts
Acquisition cost ratio	23.0		%	22.1		%	0.9		pts
Other underwriting expense ratio	3.9		%	5.9		%	(2.0		pts)
Combined ratio	93.0		%	84.3		%	8.7		pts

•Gross premiums written increased by $43.7 million, or 11.9%, to $411.0 million, primarily driven by growth in both new and existing business in casualty and specialty reinsurance classes, partially offset by a decrease in property reinsurance and insurance classes, primarily as a result of pressure on rates.

•The attritional loss ratio (current year), net of reinsurance, was 55.7%. The increase of 1.5 points was primarily driven by a change in business mix, including an increase in casualty reinsurance business.

•Net unfavorable attritional prior year reserve development, net of reinsurance, was $13.0 million, primarily driven by unfavorable development on certain casualty classes, partially offset by favorable development in property classes.

•Catastrophe losses (current and prior year), net of reinsurance, were $16.2 million, primarily driven by the Middle East conflict ($12.0 million) and unfavorable prior year development ($4.2 million).

•The acquisition cost ratio increased by 0.9 points compared to the same period in 2025, primarily driven by a change in business mix.

•The other underwriting expense ratio decreased by 2.0 points compared to the same period in 2025, primarily driven by Bermuda substance-based tax credits, increased performance based management fees, which offset the other underwriting expense ratio and an increase in net premiums earned.

Consolidated Results – Year to Date


	For the Six Months Ended
($ in thousands, except for per share amounts and percentages)	June 30, 2026		June 30, 2025		Change
Gross premiums written	$	1,771,152	$	1,555,332	$	215,820
Net premiums written	1,275,355		1,160,189		115,166
Net premiums earned	1,156,522		1,010,091		146,431
Underwriting income (loss)	$	86,695	$	9,199	$	77,496
Combined ratio	92.5%		99.1%		(6.6 pts)

Net income (loss) attributable to common shareholders	$	277,320	$	268,288	$	9,032
Income (loss) per share attributable to common shareholders - diluted	$	2.73	$	2.56
Book value per common share	$	28.91	$	25.55

Accumulated dividends	$	2.00	$	—
Book value per common share plus accumulated dividends	30.91		25.55
Change in book value per common share plus accumulated dividends	8.5%		11.3%

Return on average common equity - annualized	19.6%		22.0%


	For the Six Months Ended
Key Ratios	June 30, 2026		June 30, 2025		Change
Attritional loss ratio - current year	53.9	%	52.5	%	1.4	pts
Attritional loss ratio - prior year	1.1	%	(1.7	%)	2.8	pts
Catastrophe loss ratio - current year	4.0	%	16.8	%	(12.8	pts)
Catastrophe loss ratio - prior year	0.3	%	(1.7	%)	2.0	pts
Loss and loss adjustment expense ratio	59.3	%	65.9	%	(6.6	pts)
Acquisition cost ratio	25.1	%	23.7	%	1.4	pts
Other underwriting expense ratio	8.1	%	9.5	%	(1.4	pts)
Combined ratio	92.5	%	99.1	%	(6.6	pts)

•Gross premiums written increased by $215.8 million, or 13.9%, to $1.8 billion, with an increase of $148.2 million, or 20.7%, in the International Segment, and $67.6 million, or 8.0%, in the Bermuda Segment.

•Net premiums written increased by $115.2 million, or 9.9%, to $1.3 billion, with an increase of $123.2 million, or 25.3%, in the International Segment, and a decrease of $8.1 million, or 1.2%, in the Bermuda Segment.

•Net premiums earned increased by $146.4 million, or 14.5%, to $1.2 billion, with an increase of $99.6 million, or 20.2%, in the International Segment, and $46.8 million, or 9.1%, in the Bermuda Segment.

•The attritional loss ratio (current year), net of reinsurance, was 53.9%. The increase of 1.4 points was primarily driven by a change in business mix, including more casualty reinsurance and specialty insurance business.

•Net unfavorable attritional prior year reserve development, net of reinsurance, was $13.1 million, primarily driven by additional loss information in relation to the Baltimore Bridge collapse and unfavorable development in certain casualty classes, partially offset by favorable development in specialty and property classes.

•The acquisition cost ratio increased by 1.4 points compared to the same period in 2025, primarily driven by a change in business mix.

•The other underwriting expense ratio decreased by 1.4 points compared to the same period in 2025, primarily driven by Bermuda substance-based tax credits and an increase in net premiums earned.

International Segment Underwriting Results – Year to Date


International Segment	For the Six Months Ended
($ in thousands, except for percentages)	June 30, 2026			June 30, 2025			Change
Gross premiums written	$	862,982		$	714,757		$	148,225
Net premiums written	610,280			487,063			123,217
Net premiums earned	593,414			493,775			99,639
Underwriting income (loss)	$	16,104		$	27,931		$	(11,827)

Key Ratios
Attritional loss ratio - current year	53.0		%	52.0		%	1.0		pts
Attritional loss ratio - prior year	(1.7		%)	(3.3		%)	1.6		pts
Catastrophe loss ratio - current year	5.7		%	6.2		%	(0.5		pts)
Catastrophe loss ratio - prior year	0.0		%	(0.1		%)	0.1		pts
Loss and loss adjustment expense ratio	57.0		%	54.8		%	2.2		pts
Acquisition cost ratio	27.2		%	26.0		%	1.2		pts
Other underwriting expense ratio	13.1		%	13.6		%	(0.5		pts)
Combined ratio	97.3		%	94.4		%	2.9		pts

•Gross premiums written increased by $148.2 million, or 20.7%, to $863.0 million, primarily driven by growth in both new and existing business in casualty and specialty insurance classes.

•The attritional loss ratio (current year), net of reinsurance, was 53.0%, an increase of 1.0 point compared to the same period in 2025, primarily driven by a change in business mix, including more specialty insurance business.

•Net favorable attritional prior year reserve development, net of reinsurance, was $9.9 million, primarily driven by favorable development in specialty, property and casualty classes, partially offset by additional loss information in relation to the Baltimore Bridge collapse.

•Catastrophe losses (current and prior year), net of reinsurance, were $33.6 million, driven by the Middle East conflict.

•The acquisition cost ratio increased by 1.2 points compared to the same period in 2025, primarily driven by a change in business mix.

•The other underwriting expense ratio decreased by 0.5 points compared to the same period in 2025.

Bermuda Segment Underwriting Results – Year to Date


Bermuda Segment	For the Six Months Ended
($ in thousands, except for percentages)	June 30, 2026			June 30, 2025			Change
Gross premiums written	$	908,170		$	840,575		$	67,595
Net premiums written	665,075			673,126			(8,051)
Net premiums earned	563,108			516,316			46,792
Underwriting income (loss)	$	70,591		$	(18,732)		$	89,323

Key Ratios
Attritional loss ratio - current year	54.9		%	53.0		%	1.9		pts
Attritional loss ratio - prior year	4.1		%	(0.1		%)	4.2		pts
Catastrophe loss ratio - current year	2.1		%	26.9		%	(24.8		pts)
Catastrophe loss ratio - prior year	0.7		%	(3.3		%)	4.0		pts
Loss and loss adjustment expense ratio	61.8		%	76.5		%	(14.7		pts)
Acquisition cost ratio	22.8		%	21.5		%	1.3		pts
Other underwriting expense ratio	2.8		%	5.6		%	(2.8		pts)
Combined ratio	87.4		%	103.6		%	(16.2		pts)

•Gross premiums written increased by $67.6 million, or 8.0%, to $908.2 million, primarily driven by growth in both new and existing business in casualty reinsurance classes, partially offset by a decrease in property reinsurance classes as a result of lower reinstatement premiums and pressure on rates.

•The attritional loss ratio (current year), net of reinsurance, was 54.9%. The increase of 1.9 points was primarily driven by a change in business mix, including an increase in casualty reinsurance business.

•Net unfavorable attritional prior year reserve development, net of reinsurance, was $23.0 million, primarily driven by additional loss information in relation to the Baltimore Bridge collapse and unfavorable development in certain casualty classes, partially offset by favorable development in property classes.

•The acquisition cost ratio increased by 1.3 points compared to the same period in 2025, primarily driven by a change in business mix.

•The other underwriting expense ratio decreased by 2.8 points compared to the same period in 2025, primarily driven by Bermuda substance-based tax credits, increased performance based management fees, which offset the other underwriting expense ratio, and an increase in net premiums earned.

Investments and Shareholders’ Equity as of June 30, 2026

•Total cash and invested assets of $6.1 billion compared to $5.9 billion at December 31, 2025.

•Total shareholders’ equity of $2.9 billion compared to $2.8 billion at December 31, 2025.

•Book value per share of $28.91 compared to $28.50 at December 31, 2025, an increase of 1.4%.

•Book value per share plus accumulated dividends, of $30.91 compared to $28.50 at December 31, 2025, an increase of 8.5%.

Conference Call Details and Additional Information

Conference Call Information

Hamilton will host a conference call to discuss its financial results on Friday, August 7, 2026, at 9:30 a.m. Eastern Time. A live, audio webcast of the conference call can be accessed through the Investors portal of the Company’s website at investors.hamiltongroup.com where a replay of the call will also be available.

For access to the webcast, please log in a few minutes in advance to complete any necessary registration.

Additional Information

In addition to the information provided in the Company's earnings release, we have also made available supplementary financial information and an investor presentation which may be referred to during the conference call and will be available on the Company’s website at investors.hamiltongroup.com.

About Hamilton Insurance Group, Ltd.

Hamilton is a Bermuda-headquartered specialty insurance and reinsurance company that underwrites risks on a global basis through its wholly owned subsidiaries. Its three underwriting platforms: Hamilton Global Specialty, Hamilton Select and Hamilton Re, each with dedicated and experienced leadership, provide access to diversified and profitable business around the world.

For more information about Hamilton, visit our website at www.hamiltongroup.com or find us on LinkedIn at Hamilton.

Consolidated Balance Sheet


($ in thousands, except share information)	June 30, 2026		December 31, 2025
Assets
Fixed maturity investments, at fair value (amortized cost 2026: $3,133,507; 2025: $3,210,940)	$	3,114,054	$	3,238,543
Short-term investments, at fair value (amortized cost 2026: $355,729; 2025: $200,052)	356,453		200,459
Investments in Two Sigma Funds, at fair value (cost 2026: $1,574,091; 2025: $1,355,563)	1,844,158		1,587,658
Total investments	5,314,665		5,026,660
Cash and cash equivalents	717,335		1,062,359
Restricted cash and cash equivalents	111,631		109,731
Premiums receivable	1,240,034		939,777
Paid losses recoverable	99,228		93,659
Deferred acquisition costs	294,669		257,203
Unpaid losses and loss adjustment expenses recoverable	1,463,936		1,375,857
Receivables for investments sold	185,133		58,029
Prepaid reinsurance	454,535		296,351
Intangible assets	83,163		86,624
Other assets	299,570		265,363
Total assets	$	10,263,899	$	9,571,613

Liabilities, non-controlling interest, and shareholders' equity
Liabilities
Reserve for losses and loss adjustment expenses	$	4,783,094	$	4,415,176
Unearned premiums	1,654,491		1,377,474
Reinsurance balances payable	491,148		296,400
Payables for investments purchased	61,071		209,853
Term loan, net of issuance costs	149,795		149,743
Accounts payable and accrued expenses	131,905		177,320
Payables to related parties	67,946		123,376
Total liabilities	7,339,450		6,749,342

Non-controlling interest – TS Hamilton Fund	73,613		172

Shareholders’ equity
Common shares:
Class A, authorized (2026 and 2025: 26,444,807), par value $0.01; issued and outstanding (2026 and 2025: 17,320,078)	173		173
Class B, authorized (2026 and 2025: 84,677,932), par value $0.01; issued and outstanding (2026: 65,890,659 and 2025: 66,305,707)	659		663
Class C, authorized (2026 and 2025: 15,403,649), par value $0.01; issued and outstanding (2026 and 2025: 15,403,649)	154		154
Additional paid-in capital	1,126,425		1,134,985
Accumulated other comprehensive loss	(4,441)		(4,441)
Retained earnings	1,727,866		1,690,565
Total shareholders' equity	2,850,836		2,822,099

Total liabilities, non-controlling interest, and shareholders' equity	$	10,263,899	$	9,571,613

Consolidated Statement of Operations


	Three Months Ended				Six Months Ended
	June 30,				June 30,
($ in thousands, except for per share amounts)	2026		2025		2026		2025
Revenues
Gross premiums written	$	831,041	$	712,026	$	1,771,152	$	1,555,332
Reinsurance premiums ceded	(209,346)		(155,712)		(495,797)		(395,143)
Net premiums written	621,695		556,314		1,275,355		1,160,189

Net change in unearned premiums	(35,688)		(45,151)		(118,833)		(150,098)
Net premiums earned	586,007		511,163		1,156,522		1,010,091

Net realized and unrealized gains (losses) on investments	227,856		208,034		378,933		456,828
Net investment income (loss)	24,440		21,067		50,469		39,994
Total net realized and unrealized gains (losses) on investments and net investment income (loss)	252,296		229,101		429,402		496,822


Other income (loss)	3,904		5,014		10,655		9,676
Net foreign exchange gains (losses)	(2,629)		(4,513)		1,905		(7,039)
Total revenues	839,578		740,765		1,598,484		1,509,550

Expenses
Losses and loss adjustment expenses	361,489		269,928		686,274		665,163
Acquisition costs	145,423		122,815		289,929		239,696
General and administrative expenses	66,931		68,828		128,395		131,530

Amortization of intangible assets	3,700		4,004		7,720		7,895
Interest expense	4,762		4,729		9,538		10,331
Total expenses	582,305		470,304		1,121,856		1,054,615

Income (loss) before income tax	257,273		270,461		476,628		454,935
Income tax expense (benefit)	2,470		2,675		4,793		5,882
Net income (loss)	254,803		267,786		471,835		449,053

Net income (loss) attributable to non-controlling interest	111,021		80,371		194,515		180,765

Net income (loss) and other comprehensive income (loss) attributable to common shareholders	$	143,782	$	187,415	$	277,320	$	268,288

Per share data
Basic income (loss) per share attributable to common shareholders	$	1.45	$	1.85	$	2.79	$	2.64
Diluted income (loss) per share attributable to common shareholders	$	1.42	$	1.79	$	2.73	$	2.56

Non-GAAP Financial Measures Reconciliation

We present our results of operations in a way that we believe will be the most meaningful and useful to investors, analysts, rating agencies and others who use our financial information to evaluate our performance. Some of the measurements that management uses to assess our operating results are considered non-GAAP financial measures under Regulation G and Item 10(e) of Regulation S-K, each promulgated by the SEC. We believe that these non-GAAP financial measures, which may be defined and calculated differently by other companies, help explain and enhance the understanding of our results of operations. However, these measures should not be viewed as a substitute for those determined in accordance with U.S. GAAP. Where appropriate, reconciliations of our non-GAAP measures to the most directly comparable GAAP financial measures are included below.

Operating Income (Loss) Attributable to Common Shareholders, Operating Income (Loss) Attributable to Common Shareholders per Common Share - Diluted and Operating Return on Average Common Shareholders' Equity - Annualized

Operating income (loss) attributable to common shareholders, as used herein, differs from net income (loss) and other comprehensive income (loss) attributable to common shareholders, which we believe is the most directly comparable GAAP measure, by the exclusion of net realized and unrealized gains and losses on fixed maturity and short term investments, and net foreign exchange gains and losses. We also use operating income (loss) attributable to common shareholders to calculate operating income (loss) attributable to common shareholders per common share - diluted and operating return on average common shareholders' equity - annualized.

We believe that operating income (loss) attributable to common shareholders, operating income (loss) attributable to common shareholders per common share - diluted and operating return on average common shareholders' equity - annualized are meaningful and useful to investors, analysts, rating agencies and others who use our financial information to evaluate our performance.

The following tables are a reconciliation of: net income (loss) and other comprehensive income (loss) attributable to common shareholders to operating income (loss) attributable to common shareholders; net income (loss) and other comprehensive income (loss) attributable to common shareholders per common share - diluted to operating income (loss) attributable to common shareholders per common share - diluted; and return on average common shareholders' equity - annualized to operating return on average common shareholders' equity - annualized. Comparative information for the prior periods presented have been updated to conform to the current methodology and presentation.


	Three Months Ended				Six Months Ended
	June 30,				June 30,
($ in thousands, except for per share amounts)	2026		2025		2026		2025
Net income (loss) and other comprehensive income (loss) attributable to common shareholders	$	143,782	$	187,415	$	277,320	$	268,288
Adjustment for:
Net realized (gains) losses on investments - Fixed maturity and short-term investments(1)	5,241		(1,343)		2,332		(867)
Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1)	6,529		(28,782)		47,171		(63,269)
Net foreign exchange (gains) losses	2,629		4,513		(1,905)		7,039
Operating income (loss) attributable to common shareholders	$	158,181	$	161,803	$	324,918	$	211,191


Net income (loss) and other comprehensive income (loss) attributable to common shareholders per common share - diluted	$	1.42	$	1.79	$	2.73	$	2.56
Adjustment for:
Net realized (gains) losses on investments - Fixed maturity and short-term investments(1)	0.05		(0.01)		0.02		(0.01)
Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1)	0.06		(0.27)		0.46		(0.60)
Net foreign exchange (gains) losses	0.03		0.04		(0.01)		0.06
Operating income (loss) attributable to common shareholders per common share - diluted	$	1.56	$	1.55	$	3.20	$	2.01


Return on average common shareholders' equity - annualized	20.6	%	30.2	%	19.6	%	22.0	%
Adjustment for:
Net realized (gains) losses on investments - Fixed maturity and short-term investments(1)	0.8	%	(0.2)	%	0.2	%	(0.1)	%
Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1)	0.9	%	(4.6)	%	3.3	%	(5.2)	%
Net foreign exchange (gains) losses	0.4	%	0.7	%	(0.2)	%	0.6	%
Operating return on average common shareholders' equity - annualized	22.7	%	26.1	%	22.9	%	17.3	%

(1) Fixed income portfolio managed by our external investment managers only

Underwriting Income (Loss)

We calculate underwriting income (loss) on a pre-tax basis as net premiums earned less losses and loss adjustment expenses, acquisition costs and other underwriting expenses (net of third party fee income). We believe that this measure of our performance focuses on the core fundamental performance of the Company’s reportable segments in any given period and is not distorted by investment market conditions, corporate expense allocations or income tax effects.

The following table reconciles underwriting income (loss) to net income (loss), the most directly comparable GAAP financial measure:


	Three Months Ended				Six Months Ended
	June 30,				June 30,
($ in thousands)	2026		2025		2026		2025
Underwriting income (loss)	$	29,112	$	67,459	$	86,695	$	9,199
Total net realized and unrealized gains (losses) on investments and net investment income (loss)	252,296		229,101		429,402		496,822


Net foreign exchange gains (losses)	(2,629)		(4,513)		1,905		(7,039)
Corporate expenses	(13,044)		(12,853)		(24,116)		(25,821)

Amortization of intangible assets	(3,700)		(4,004)		(7,720)		(7,895)
Interest expense	(4,762)		(4,729)		(9,538)		(10,331)
Income tax (expense) benefit	(2,470)		(2,675)		(4,793)		(5,882)
Net income (loss), prior to non-controlling interest	$	254,803	$	267,786	$	471,835	$	449,053

Third Party Fee Income

Third party fee income includes income that is incremental and/or directly attributable to our underwriting operations. It is primarily compromised of performance and management fees earned by the Bermuda segment that were generated by our third party capital manager, Ada Capital Management Limited, and fees earned by the International segment for management services provided to consortia and third party syndicates. We believe that this measure is a relevant component of our underwriting income (loss).

The following table reconciles third party fee income to other income, the most directly comparable GAAP financial measure:


	Three Months Ended				Six Months Ended
	June 30,				June 30,
($ in thousands)	2026		2025		2026		2025
Third party fee income	$	3,904	$	5,014	$	10,655	$	9,676

Other income (loss)	$	3,904	$	5,014	$	10,655	$	9,676

Other Underwriting Expenses

Other underwriting expenses include those general and administrative expenses that are incremental and/or directly attributable to our underwriting operations. While this measure is presented in Note 8, Segment Reporting in the unaudited condensed consolidated financial statements, it is considered a non-GAAP financial measure when presented elsewhere.

Corporate expenses include holding company costs necessary to support our reportable segments. As these costs are not incremental and/or directly attributable to our underwriting operations, these costs are excluded from other underwriting expenses, and therefore, underwriting income (loss). General and administrative expenses, the most comparable GAAP financial measure to other underwriting expenses, also includes corporate expenses.

The following table reconciles other underwriting expenses to general and administrative expenses, the most directly comparable GAAP financial measure:


	Three Months Ended				Six Months Ended
	June 30,				June 30,
($ in thousands)	2026		2025		2026		2025
Other underwriting expenses	$	53,887	$	55,975	$	104,279	$	105,709
Corporate expenses	13,044		12,853		24,116		25,821
General and administrative expenses	$	66,931	$	68,828	$	128,395	$	131,530

Other Underwriting Expense Ratio

Other Underwriting Expense Ratio is a measure of the other underwriting expenses (net of third party fee income) incurred by the Company and is expressed as a percentage of net premiums earned.

Loss Ratio

Attritional Loss Ratio – current year is the attritional losses incurred by the company relating to the current year divided by net premiums earned.

Attritional Loss Ratio – prior year development is the attritional losses incurred by the company relating to prior years divided by net premiums earned.

Catastrophe Loss Ratio – current year is the catastrophe losses incurred by the company relating to the current year divided by net premiums earned.

Catastrophe Loss Ratio – prior year development is the catastrophe losses incurred by the company relating to prior years divided by net premiums earned.

Combined Ratio

Combined Ratio is a measure of our underwriting profitability and is expressed as the sum of the loss and loss adjustment expense ratio, acquisition cost ratio and other underwriting expense ratio. A combined ratio under 100% indicates an underwriting profit, while a combined ratio over 100% indicates an underwriting loss.

Special Note Regarding Forward-Looking Statements

This information includes “forward looking statements” pursuant to the safe harbor provisions of the U.S. Private Securities Litigation Reform Act of 1995. Forward-looking statements can be identified by the use of terms such as “believes,” “expects,” “may,” “will,” “target,” “should,” “could,” “would,” “seeks,” “intends,” “plans,” “contemplates,” “estimates,” “forecasts,” or “anticipates,” or similar expressions which concern our strategy, plans, projections or intentions. These forward-looking statements appear in a number of places throughout and relate to matters such as our industry, growth strategy, goals and expectations concerning our market position, future operations, margins, profitability, capital expenditures, liquidity and capital resources, business plans (including syndicate capacity forecasts), and other financial and operating information. By their nature, forward-looking statements: speak only as of the date they are made; are not statements of historical fact or guarantees of future performance; and are subject to risks, uncertainties, assumptions, or changes in circumstances that are difficult to predict or quantify. Our expectations, beliefs, and projections are expressed in good faith and we believe there is a reasonable basis for them. However, there can be no assurance that management’s expectations, beliefs and projections will be achieved and actual results may vary materially from what is expressed in or indicated by the forward-looking statements.

There are a number of risks, uncertainties, and other important factors that could cause our actual results to differ materially from the forward-looking statements contained herein. Such risks, uncertainties, and other important factors include, among others, the risks, uncertainties and factors set forth in “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” included in the Company’s Annual Report on Form 10-K for the year ended December 31, 2025 (the “Form 10-K”), our other subsequent periodic reports filed with the Securities and Exchange Commission and the following:

•challenges from competitors, including those arising from industry consolidation, alternative capital and technological advancements, including the increasing use of advanced analytics and artificial intelligence;

•unpredictable events, including natural catastrophes and man‑made disasters, global climate change and emerging claim, litigation and coverage issues that may increase loss severity or expand coverage obligations;

•our ability, or that of the third parties on which we rely, to ensure reserves are adequate to cover actual losses and to accurately assess underwriting risk, models, assumptions, data quality and the pricing of risks, particularly in long‑tail, low‑frequency or emerging lines of business;

•our ability to defend and protect our intellectual property rights, including our proprietary technology platforms and data, to comply with obligations under license and technology agreements or to obtain or renew licenses to technology or data on reasonable terms;

•the impact of risks associated with human error, misconduct or fraud, model uncertainty, cybersecurity threats such as cyber‑attacks and security breaches, misuse of artificial intelligence and our reliance on third‑party information technology systems that may fail, be disrupted or require replacement;

•our ability to secure necessary credit facilities, letters of credit or other forms of financing or collateral on favorable terms or at all;

•our limited financial and operational flexibility due to covenants and other restrictions in our existing or future credit facilities and debt arrangements;

•our exposure to the credit risk of insurance and reinsurance intermediaries on which we rely for the collection of premiums and payment of claims;

•our failure to pay claims in a timely manner, significant reserve strengthening, or the need to sell investments under unfavorable market or other conditions in order to meet liquidity requirements;

•downgrades, potential downgrades or other negative actions by rating agencies, including changes in rating agency methodologies;

•our ability to manage risks associated with adverse macroeconomic conditions, geopolitical instability and global events, including current or anticipated military conflicts, public health crises, terrorism, sanctions, inflation, rising interest rates, energy price volatility and other disruptions;

•the cyclical nature of the insurance and reinsurance business, which may result in declines in pricing and more competitive terms and conditions;

•our results of operations fluctuating significantly from period to period and not being indicative of our long‑term prospects;

•our ability to execute our strategy and to adapt our business and strategic plans in response to changing market, regulatory and competitive conditions;

•our dependence on key executives and other personnel, including the potential loss of Bermudian or other critical personnel, and our ability to attract and retain qualified employees in highly competitive labor markets;

•foreign operational risks, including foreign currency risk, political instability, regulatory uncertainty and differing legal regimes in jurisdictions where we operate;

•our ability to identify, execute and integrate growth opportunities, including acquisitions or other strategic transactions, and to realize the anticipated benefits of such initiatives;

•risks arising from our management of alternative reinsurance platforms and vehicles for third‑party investors;

•our inability to control the asset allocation, investment decisions or performance of the Two Sigma Hamilton Fund, LLC (the “TS Hamilton Fund”) and our limited ability to withdraw capital from the TS Hamilton Fund;

•conflicts of interest, governance, operational or regulatory risks involving Two Sigma Investments, LP (“Two Sigma”), the TS Hamilton Fund or their respective affiliates that could adversely affect investment performance or our business;

•the historical performance of Two Sigma or the TS Hamilton Fund not being indicative of future performance or our future results;

•risks associated with our investment strategy, including the use of leverage, derivatives, illiquid assets and concentration risk, which may be greater than those faced by some of our competitors;

•our potentially becoming subject to additional or increased taxation, including U.S. federal income tax, Bermuda tax or other taxes, as a result of changes in tax laws, interpretations or our operations;

•the potential classification of us or our subsidiaries as a passive foreign investment company or becoming subject to U.S. withholding and information reporting requirements under the U.S. Foreign Account Tax Compliance Act;

•our ability to compete effectively in a highly regulated industry in light of new or changing domestic or international laws and regulations, including accounting standards and evolving regulatory interpretations;

•the suspension, limitation or revocation of licenses or approvals required by our insurance and reinsurance subsidiaries;

•significant legal, regulatory or governmental proceedings or investigations;

•restrictions on our insurance and reinsurance subsidiaries’ ability to pay dividends or make other distributions to us;

•challenges and costs associated with compliance with public company disclosure, governance and internal control requirements;

•the limited ability of investors to influence corporate matters due to our multi‑class share structure and the voting provisions in our Bye‑laws;

•the risk that anti‑takeover provisions in our Bye‑laws or Bermuda law could discourage, delay or prevent a change in control, even if beneficial to shareholders; and

•difficulties investors may face in enforcing judgments or protecting their interests against us or our directors and officers.

There may be other factors that could cause our actual results to differ materially from the forward-looking statements. You should evaluate all forward-looking statements made herein in the context of these risks and uncertainties.

You should read this information completely and with the understanding that actual future results may be materially different from expectations. We caution you that the risks, uncertainties, and other factors referenced above may not contain all of the risks, uncertainties and other factors that are important to you. In addition, we cannot assure you that we will realize the results, benefits, or developments that we expect or anticipate or, even if substantially realized, that they will result in the consequences or affect us or our business in the way expected. All forward-looking statements contained herein apply only as of the date hereof and are expressly qualified in their entirety by these cautionary statements. We undertake no obligation to publicly update or revise any forward-looking statements to reflect subsequent events or circumstances.

Investor contact:

Darian Niforatos

Investor.Relations@hamiltongroup.com

Media contact:

Kelly Corday Ferris

kelly.ferris@hamiltongroup.com

Hamilton Insurance Group, Ltd. Supplementary Financial Information June 30, 2026 Investor Contact Investor.Relations@hamiltongroup.com

Hamilton Insurance Group, Ltd. Table of Contents Page I. Basis of Presentation ......................................................................................................................................................................................................... 1 II. Financial Highlights Financial Highlights ............................................................................................................................................................................................................... 4 Key Operating and Financial Metrics ................................................................................................................................................................................. 5 III. Summary Consolidated Results Statements of Operations ................................................................................................................................................................................................... 6 Consolidated Balance Sheets ............................................................................................................................................................................................. 7 Reconciliation of Consolidated GAAP Balance Sheet to Unconsolidated Balance Sheet ....................................................................................... 8 Net Investment Return ......................................................................................................................................................................................................... 9 Fixed Maturity and Short-Term Investments ..................................................................................................................................................................... 10 IV. Segment Results Consolidated Underwriting Results .................................................................................................................................................................................... 11 5Q Consolidated Underwriting Results - Group ............................................................................................................................................................... 13 5Q Underwriting Results - International ............................................................................................................................................................................ 14 5Q Underwriting Results - Bermuda .................................................................................................................................................................................. 15 V. Other Information Modeled Exposure to Catastrophe Losses (PML) .......................................................................................................................................................... 16 Non-GAAP Measures ........................................................................................................................................................................................................... 17

1 Basis of Presentation All financial information contained herein is unaudited, however, certain information relating to the consolidated balance sheet at the most recent year end is derived from or agrees to audited financial information. Unless otherwise noted, all data is in thousands, except for share and per share amounts and ratio information. This presentation is being provided for informational purposes only. It should be read in conjunction with the documents filed by Hamilton Insurance Group, Ltd. (referred to herein, together with its subsidiaries unless the context otherwise requires, as "Hamilton," the "Company," "we," "us" and "our") with the U.S. Securities and Exchange Commission (the "SEC"), including it's Form 10-Q. Special Note Regarding Forward-Looking Statements This presentation includes “forward looking statements” pursuant to the safe harbor provisions of the U.S. Private Securities Litigation Reform Act of 1995. Forward-looking statements can be identified by the use of terms such as “believes,” “expects,” “may,” “will,” “target,” “should,” “could,” “would,” “seeks,” “intends,” “plans,” “contemplates,” “estimates,” "forecasts," or “anticipates,” or similar expressions which concern our strategy, plans, projections or intentions. These forward-looking statements appear in a number of places throughout and relate to matters such as our industry, growth strategy, goals and expectations concerning our market position, future operations, margins, profitability, capital expenditures, liquidity and capital resources, business plans (including syndicate capacity forecasts), and other financial and operating information. By their nature, forward-looking statements: speak only as of the date they are made; are not statements of historical fact or guarantees of future performance; and are subject to risks, uncertainties, assumptions, or changes in circumstances that are difficult to predict or quantify. Our expectations, beliefs, and projections are expressed in good faith and we believe there is a reasonable basis for them. However, there can be no assurance that management’s expectations, beliefs and projections will be achieved and actual results may vary materially from what is expressed in or indicated by the forward-looking statements. There are a number of risks, uncertainties, and other important factors that could cause our actual results to differ materially from the forward-looking statements contained herein. Such risks, uncertainties, and other important factors include, among others, the risks, uncertainties and factors set forth in “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” included in the Company's Annual Report on Form 10-K for the year ended December 31, 2025, our other subsequent periodic reports filed with the SEC and the following: • challenges from competitors, including those arising from industry consolidation, alternative capital and technological advancements, including the increasing use of advanced analytics and artificial intelligence; • unpredictable events, including natural catastrophes and man-made disasters, global climate change and emerging claim, litigation and coverage issues that may increase loss severity or expand coverage obligations; • our ability, or that of the third parties on which we rely, to ensure reserves are adequate to cover actual losses and to accurately assess underwriting risk, models, assumptions, data quality and the pricing of risks, particularly in long-tail, low-frequency or emerging lines of business; • our ability to defend and protect our intellectual property rights, including our proprietary technology platforms and data, to comply with obligations under license and technology agreements or to obtain or renew licenses to technology or data on reasonable terms; • the impact of risks associated with human error, misconduct or fraud, model uncertainty, cybersecurity threats such as cyber-attacks and security breaches, misuse of artificial intelligence and our reliance on third-party information technology systems that may fail, be disrupted or require replacement; • our ability to secure necessary credit facilities, letters of credit or other forms of financing or collateral on favorable terms or at all;

2 Basis of Presentation Special Note Regarding Forward-Looking Statements (continued) • our limited financial and operational flexibility due to covenants and other restrictions in our existing or future credit facilities and debt arrangements; • our exposure to the credit risk of insurance and reinsurance intermediaries on which we rely for the collection of premiums and payment of claims; • our failure to pay claims in a timely manner, significant reserve strengthening, or the need to sell investments under unfavorable market or other conditions in order to meet liquidity requirements; • downgrades, potential downgrades or other negative actions by rating agencies, including changes in rating agency methodologies; • our ability to manage risks associated with adverse macroeconomic conditions, geopolitical instability and global events, including current or anticipated military conflicts, public health crises, terrorism, sanctions, inflation, rising interest rates, energy price volatility and other disruptions; • the cyclical nature of the insurance and reinsurance business, which may result in declines in pricing and more competitive terms and conditions; • our results of operations fluctuating significantly from period to period and not being indicative of our long-term prospects; • our ability to execute our strategy and to adapt our business and strategic plans in response to changing market, regulatory and competitive conditions; • our dependence on key executives and other personnel, including the potential loss of Bermudian or other critical personnel, and our ability to attract and retain qualified employees in highly competitive labor markets; • foreign operational risks, including foreign currency risk, political instability, regulatory uncertainty and differing legal regimes in jurisdictions where we operate; • our ability to identify, execute and integrate growth opportunities, including acquisitions or other strategic transactions, and to realize the anticipated benefits of such initiatives; • risks arising from our management of alternative reinsurance platforms and vehicles for third-party investors; • our inability to control the asset allocation, investment decisions or performance of the Two Sigma Hamilton Fund, LLC (the "TS Hamilton Fund") and our limited ability to withdraw capital from the TS Hamilton Fund; • conflicts of interest, governance, operational or regulatory risks involving Two Sigma Investments, LP ("Two Sigma"), the TS Hamilton Fund or their respective affiliates that could adversely affect investment performance or our business; • the historical performance of Two Sigma or the TS Hamilton Fund not being indicative of future performance or our future results; • risks associated with our investment strategy, including the use of leverage, derivatives, illiquid assets and concentration risk, which may be greater than those faced by some of our competitors; • our potentially becoming subject to additional or increased taxation, including U.S. federal income tax, Bermuda tax or other taxes, as a result of changes in tax laws, interpretations or our operations; • the potential classification of us or our subsidiaries as a passive foreign investment company or becoming subject to U.S. withholding and information reporting requirements under the U.S. Foreign Account Tax Compliance Act; • our ability to compete effectively in a highly regulated industry in light of new or changing domestic or international laws and regulations, including accounting standards and evolving regulatory interpretations; • the suspension, limitation or revocation of licenses or approvals required by our insurance and reinsurance subsidiaries; • significant legal, regulatory or governmental proceedings or investigations; • restrictions on our insurance and reinsurance subsidiaries’ ability to pay dividends or make other distributions to us; • challenges and costs associated with compliance with public company disclosure, governance and internal control requirements; • the limited ability of investors to influence corporate matters due to our multi-class share structure and the voting provisions in our Bye-laws;

3 Basis of Presentation Special Note Regarding Forward-Looking Statements (continued) • the risk that anti-takeover provisions in our Bye-laws or Bermuda law could discourage, delay or prevent a change in control, even if beneficial to shareholders; and • difficulties investors may face in enforcing judgments or protecting their interests against us or our directors and officers. There may be other factors that could cause our actual results to differ materially from the forward-looking statements. You should evaluate all forward- looking statements made herein in the context of these risks and uncertainties. You should read this information completely and with the understanding that actual future results may be materially different from expectations. We caution you that the risks, uncertainties, and other factors referenced above may not contain all of the risks, uncertainties and other factors that are important to you. In addition, we cannot assure you that we will realize the results, benefits, or developments that we expect or anticipate or, even if substantially realized, that they will result in the consequences or affect us or our business in the way expected. All forward-looking statements contained herein apply only as of the date hereof and are expressly qualified in their entirety by these cautionary statements. We undertake no obligation to publicly update or revise any forward-looking statements to reflect subsequent events or circumstances.

4 Financial Highlights Three Months Ended June 30, Six Months Ended June 30, Year Ended ($ in thousands) 2026 2025 2026 2025 2025 Net income (loss) attributable to common shareholders ........................................................ $ 143,782 $ 187,415 $ 277,320 $ 268,288 $ 576,670 Operating income (loss) attributable to common shareholders ............................................ $ 158,181 $ 161,803 $ 324,918 $ 211,191 $ 502,515 Underwriting income (loss) Gross premiums written ............................................................................................................... $ 831,041 $ 712,026 $ 1,771,152 $ 1,555,332 $ 2,923,145 Net premiums written ................................................................................................................... 621,695 556,314 1,275,355 1,160,189 2,287,543 Net premiums earned .................................................................................................................. 586,007 511,163 1,156,522 1,010,091 2,109,776 Underwriting income (loss) .......................................................................................................... $ 29,112 $ 67,459 $ 86,695 $ 9,199 $ 148,823 Key Ratios: Attritional loss ratio - current year .............................................................................................. 53.3 % 53.0 % 53.9 % 52.5 % 54.4 % Attritional loss ratio - prior year development ........................................................................... (0.1) % (0.5) % 1.1 % (1.7) % (2.2) % Catastrophe loss ratio - current year ......................................................................................... 7.8 % 1.9 % 4.0 % 16.8 % 8.4 % Catastrophe loss ratio - prior year development ...................................................................... 0.7 % (1.6) % 0.3 % (1.7) % (0.9) % Loss and loss adjustment expense ratio ................................................................................... 61.7 % 52.8 % 59.3 % 65.9 % 59.7 % Acquisition cost ratio .................................................................................................................... 24.8 % 24.0 % 25.1 % 23.7 % 24.0 % Other underwriting expense ratio ............................................................................................... 8.5 % 10.0 % 8.1 % 9.5 % 9.2 % Combined ratio .............................................................................................................................. 95.0 % 86.8 % 92.5 % 99.1 % 92.9 % Investments Total assets .................................................................................................................................... $ 10,263,899 $ 8,913,050 $ 10,263,899 $ 8,913,050 $ 9,571,613 Total cash and invested assets(1) ............................................................................................... 6,126,134 5,321,894 6,126,134 5,321,894 5,923,378 Total investment return(2) ............................................................................................................. 141,275 148,730 234,887 316,057 511,773 Two Sigma Hamilton Fund Total net realized and unrealized gains (losses) on investments and net investment income (loss) - TSHF ................................................................................................................... 226,499 167,457 403,049 371,418 564,254 Net income (loss) attributable to non-controlling interest - TSHF ......................................... 111,021 80,371 194,515 180,765 263,359 $ 115,478 $ 87,086 $ 208,534 $ 190,653 $ 300,895 Two Sigma Hamilton Fund return, net of investment management fees and performance incentive allocations .............................................................................................. 5.1 % 4.4 % 9.6 % 10.1 % 16.0 % Fixed income, short term investments and cash and cash equivalents Total net realized and unrealized gains (losses) on investments and net investment income (loss) - other .................................................................................................................... $ 25,797 $ 61,644 $ 26,353 $ 125,404 $ 210,878 (1) Total cash and total investments, plus receivables for investments sold, less payables for investments purchased, payables to related parties (TSHF) and non-controlling interest (TSHF). (2) Net realized and unrealized gains (losses) on investments, plus net investment income (loss), less non-controlling interest.

5 Three Months Ended June 30, Six Months Ended June 30, Year Ended ($ in thousands, except per share amounts) 2026 2025 2026 2025 2025 Income (loss) per share attributable to common shareholders - basic ................................ $ 1.45 $ 1.85 $ 2.79 $ 2.64 $ 5.75 Income (loss) per share attributable to common shareholders - diluted .............................. $ 1.42 $ 1.79 $ 2.73 $ 2.56 $ 5.55 Operating income (loss) attributable to common shareholders per common share - diluted ............................................................................................................................................. $ 1.56 $ 1.55 $ 3.20 $ 2.01 $ 4.84 Weighted average common shares outstanding - basic ........................................................ 99,276,664 101,421,322 99,422,661 101,679,121 100,363,570 Weighted average common shares outstanding - diluted ...................................................... 101,085,885 104,568,161 101,461,362 104,915,497 103,844,198 Return on average common shareholders' equity - annualized ............................................ 20.6 % 30.2 % 19.6 % 22.0 % 22.4 % Operating return on average common shareholders' equity - annualized ........................... 22.7 % 26.1 % 22.9 % 17.3 % 19.5 % June 30, 2026 December 31, 2025 Closing common shareholders' equity, less intangible assets .............................................. $ 2,767,673 $ 2,735,475 Closing common shareholders' equity ...................................................................................... $ 2,850,836 $ 2,822,099 Closing common shares outstanding ........................................................................................ 98,614,386 99,029,434 Book Value per Common Share Book value per common share ................................................................................................ $ 28.91 $ 28.50 Accumulated dividends ............................................................................................................. $ 2.00 $ — Book value per common share plus accumulated dividends .............................................. $ 30.91 $ 28.50 Year to date change in book value per common share plus accumulated dividends ..... 8.5 % 24.2 % Tangible Book Value per Common Share Tangible book value per common share ................................................................................ $ 28.07 $ 27.62 Accumulated dividends ............................................................................................................. $ 2.00 $ — Tangible book value per common share plus accumulated dividends .............................. $ 30.07 $ 27.62 Year to date change in tangible book value per common share plus accumulated dividends ..................................................................................................................................... 8.9 % 25.4 % Financial Highlights Key Operating and Financial Metrics

6 Three Months Ended June 30, Six Months Ended June 30, Year Ended ($ in thousands, except per share amounts) 2026 2025 2026 2025 2025 Revenues Gross premiums written ............................................................................................................... $ 831,041 $ 712,026 $ 1,771,152 $ 1,555,332 $ 2,923,145 Reinsurance premiums ceded .................................................................................................... (209,346) (155,712) (495,797) (395,143) (635,602) Net premiums written ................................................................................................................... 621,695 556,314 1,275,355 1,160,189 2,287,543 Net change in unearned premiums ............................................................................................ (35,688) (45,151) (118,833) (150,098) (177,767) Net premiums earned .................................................................................................................. 586,007 511,163 1,156,522 1,010,091 2,109,776 Net realized and unrealized gains (losses) on investments .................................................. 227,856 208,034 378,933 456,828 687,111 Net investment income (loss) ..................................................................................................... 24,440 21,067 50,469 39,994 88,021 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ................................................................................................................................. 252,296 229,101 429,402 496,822 775,132 Third party fee income ................................................................................................................. 3,904 5,014 10,655 9,676 26,601 Net foreign exchange gains (losses) ......................................................................................... (2,629) (4,513) 1,905 (7,039) (5,985) Total revenues ............................................................................................................................. 839,578 740,765 1,598,484 1,509,550 2,905,524 Expenses Losses and loss adjustment expenses ..................................................................................... 361,489 269,928 686,274 665,163 1,258,521 Acquisition costs ........................................................................................................................... 145,423 122,815 289,929 239,696 507,290 Other underwriting expenses ...................................................................................................... 53,887 55,975 104,279 105,709 221,743 Corporate expenses ..................................................................................................................... 13,044 12,853 24,116 25,821 57,167 Amortization of intangible assets ............................................................................................... 3,700 4,004 7,720 7,895 15,709 Interest expense ........................................................................................................................... 4,762 4,729 9,538 10,331 20,189 Total expenses ............................................................................................................................ 582,305 470,304 1,121,856 1,054,615 2,080,619 Income (loss) before income tax ................................................................................................ 257,273 270,461 476,628 454,935 824,905 Income tax expense (benefit) ..................................................................................................... 2,470 2,675 4,793 5,882 (15,124) Net income (loss) ........................................................................................................................ 254,803 267,786 471,835 449,053 840,029 Net income (loss) attributable to non-controlling interest ....................................................... 111,021 80,371 194,515 180,765 263,359 Net income (loss) and other comprehensive income (loss) attributable to common shareholders .............................................................................................................. $ 143,782 $ 187,415 $ 277,320 $ 268,288 $ 576,670 Per share data Income (loss) per share attributable to common shareholders - basic ................................ $ 1.45 $ 1.85 $ 2.79 $ 2.64 $ 5.75 Income (loss) per share attributable to common shareholders - diluted .............................. $ 1.42 $ 1.79 $ 2.73 $ 2.56 $ 5.55 Return on average common shareholders' equity - annualized ............................................ 20.6 % 30.2 % 19.6 % 22.0 % 22.4 % Summary Consolidated Results Statements of Operations

7 June 30, March 31, December 31, September 30, June 30, ($ in thousands, except share information) 2026 2026 2025 2025 2025 Assets Fixed maturity investments, at fair value (amortized cost June 30, 2026: $3,133,507) ................................................. $ 3,114,054 $ 3,016,314 $ 3,238,543 $ 3,022,441 $ 2,698,470 Short-term investments, at fair value (amortized cost June 30, 2026: $355,729) .......................................................... 356,453 451,185 200,459 248,847 307,129 Investments in Two Sigma Funds, at fair value (cost June 30, 2026: $1,574,091) ........................................................ 1,844,158 1,685,031 1,587,658 1,500,672 1,453,781 Total investments ....................................................................................................................................................................... 5,314,665 5,152,530 5,026,660 4,771,960 4,459,380 Cash and cash equivalents ...................................................................................................................................................... 717,335 842,484 1,062,359 955,130 985,649 Restricted cash and cash equivalents ................................................................................................................................... 111,631 113,033 109,731 110,087 85,648 Premiums receivable ................................................................................................................................................................ 1,240,034 1,154,469 939,777 1,012,000 1,048,580 Paid losses recoverable ........................................................................................................................................................... 99,228 100,187 93,659 115,847 131,833 Deferred acquisition costs ........................................................................................................................................................ 294,669 291,312 257,203 259,260 253,402 Unpaid losses and loss adjustment expenses recoverable ................................................................................................ 1,463,936 1,412,974 1,375,857 1,303,833 1,236,660 Receivables for investments sold ........................................................................................................................................... 185,133 10,046 58,029 45,182 38,271 Prepaid reinsurance .................................................................................................................................................................. 454,535 418,978 296,351 334,025 360,890 Intangible assets ........................................................................................................................................................................ 83,163 84,331 86,624 88,848 90,061 Other assets ............................................................................................................................................................................... 299,570 283,665 265,363 217,198 222,676 Total assets .............................................................................................................................................................................. $ 10,263,899 $ 9,864,009 $ 9,571,613 $ 9,213,370 $ 8,913,050 Liabilities, non-controlling interest, and shareholders' equity Liabilities Reserve for losses and loss adjustment expenses .............................................................................................................. $ 4,783,094 $ 4,595,810 $ 4,415,176 $ 4,206,077 $ 3,984,281 Unearned premiums ................................................................................................................................................................. 1,654,491 1,583,245 1,377,474 1,443,460 1,414,344 Reinsurance balances payable ............................................................................................................................................... 491,148 460,804 296,400 372,711 417,251 Payables for investments purchased ..................................................................................................................................... 61,071 110,151 209,853 102,013 127,529 Term loan, net of issuance costs ............................................................................................................................................ 149,795 149,769 149,743 149,717 149,691 Accounts payable and accrued expenses ............................................................................................................................. 131,905 149,185 177,320 167,882 141,838 Payables to related parties ...................................................................................................................................................... 67,946 62,058 123,376 28,338 50,233 Total liabilities .......................................................................................................................................................................... 7,339,450 7,111,022 6,749,342 6,470,198 6,285,167 Non-controlling interest - TS Hamilton Fund ................................................................................................................... 73,613 30,537 172 81,179 69,292 Shareholders' equity Common shares: Class A, authorized (June 30, 2026: 26,444,807), par value $0.01; issued and outstanding (June 30, 2026: 17,320,078) ................................................................................................................................................................................ 173 173 173 178 178 Class B, authorized (June 30, 2026: 84,677,932), par value $0.01; issued and outstanding (June 30, 2026: 65,890,659) ................................................................................................................................................................................ 659 665 663 645 663 Class C, authorized (June 30, 2026: 15,403,649), par value $0.01; issued and outstanding (June 30, 2026: 15,403,649) ................................................................................................................................................................................ 154 154 154 160 160 Additional paid-in-capital .......................................................................................................................................................... 1,126,425 1,127,868 1,134,985 1,135,815 1,148,571 Accumulated other comprehensive loss ................................................................................................................................ (4,441) (4,441) (4,441) (4,441) (4,441) Retained earnings ..................................................................................................................................................................... 1,727,866 1,598,031 1,690,565 1,529,636 1,413,460 Total shareholders' equity .................................................................................................................................................... 2,850,836 2,722,450 2,822,099 2,661,993 2,558,591 Total liabilities, non-controlling interest, and shareholders' equity ......................................................................... $ 10,263,899 $ 9,864,009 $ 9,571,613 $ 9,213,370 $ 8,913,050 Summary Consolidated Results Consolidated Balance Sheets

8 June 30, 2026 ($ in thousands) Consolidated GAAP Balance Sheet Two Sigma Hamilton Fund Balances Unconsolidated Balance Sheet(1) Assets Fixed maturity investments, at fair value .................................................................................................................................................................................... $ 3,114,054 $ - $ 3,114,054 Short-term investments, at fair value ......................................................................................................................................................................................... 356,453 (356,350) 103 Investments in Two Sigma Funds, at fair value ........................................................................................................................................................................ 1,844,158 533,588 2,377,746 Total investments ............................................................................................................................................................................................................................ 5,314,665 177,238 5,491,903 Cash and cash equivalents .......................................................................................................................................................................................................... 717,335 (180,183) 537,152 Restricted cash and cash equivalents ........................................................................................................................................................................................ 111,631 - 111,631 Premiums receivable ..................................................................................................................................................................................................................... 1,240,034 - 1,240,034 Paid losses recoverable ................................................................................................................................................................................................................ 99,228 - 99,228 Deferred acquisition costs ............................................................................................................................................................................................................ 294,669 - 294,669 Unpaid losses and loss adjustment expenses recoverable .................................................................................................................................................... 1,463,936 - 1,463,936 Receivables for investments sold ................................................................................................................................................................................................ 185,133 (173,808) 11,325 Prepaid reinsurance ....................................................................................................................................................................................................................... 454,535 - 454,535 Intangible assets ............................................................................................................................................................................................................................ 83,163 - 83,163 Other assets .................................................................................................................................................................................................................................... 299,570 (1,038) 298,532 Total assets ................................................................................................................................................................................................................................... $ 10,263,899 $ (177,791) $ 10,086,108 Liabilities, non-controlling interest, and shareholders' equity Liabilities Reserve for losses and loss adjustment expenses .................................................................................................................................................................. $ 4,783,094 $ - $ 4,783,094 Unearned premiums ...................................................................................................................................................................................................................... 1,654,491 - 1,654,491 Reinsurance balances payable .................................................................................................................................................................................................... 491,148 - 491,148 Payables for investments purchased .......................................................................................................................................................................................... 61,071 (36,007) 25,064 Term loan, net of issuance costs ................................................................................................................................................................................................. 149,795 - 149,795 Accounts payable and accrued expenses .................................................................................................................................................................................. 131,905 (225) 131,680 Payables to related parties ........................................................................................................................................................................................................... 67,946 (67,946) - Total liabilities ............................................................................................................................................................................................................................... 7,339,450 (104,178) 7,235,272 Non-controlling interest - TS Hamilton Fund ....................................................................................................................................................................... 73,613 (73,613) - Shareholders' equity Common shares: Class A, par value $0.01 ............................................................................................................................................................................................................... 173 - 173 Class B, par value $0.01 ............................................................................................................................................................................................................... 659 - 659 Class C, par value $0.01 ............................................................................................................................................................................................................... 154 - 154 Additional paid-in-capital ............................................................................................................................................................................................................... 1,126,425 - 1,126,425 Accumulated other comprehensive loss ..................................................................................................................................................................................... (4,441) - (4,441) Retained earnings .......................................................................................................................................................................................................................... 1,727,866 - 1,727,866 Total shareholders' equity ......................................................................................................................................................................................................... 2,850,836 - 2,850,836 Total liabilities, non-controlling interest, and shareholders' equity .............................................................................................................................. $ 10,263,899 $ (177,791) $ 10,086,108 Summary Consolidated Results Reconciliation of Consolidated GAAP Balance Sheet to Unconsolidated Balance Sheet (1) We present our balance sheet on an unconsolidated basis above, which we believe is meaningful and useful to investors, analysts, rating agencies and others who use our financial information to evaluate our performance. The unconsolidated balances are non-GAAP financial measures, with the above table providing an appropriate reconciliation to comparable GAAP measures.

9 Three Months Ended June 30, Six Months Ended June 30, Year Ended ($ in thousands) 2026 2025 2026 2025 2025 Net realized gains (losses) on investments ........................................................................ $ 232,135 $ 196,129 $ 387,751 $ 314,787 $ 517,147 Fixed maturities and short-term investments ........................................................................ (5,241) 1,343 (2,332) 867 7,369 TS Hamilton Fund ...................................................................................................................... 237,376 194,786 390,083 313,920 509,778 Change in net unrealized gains (losses) on investments ............................................... (4,279) 11,905 (8,818) 142,041 169,964 Fixed maturities and short-term investments ........................................................................ (6,529) 28,782 (47,171) 63,269 72,771 TS Hamilton Fund ...................................................................................................................... 2,250 (16,877) 38,353 78,772 97,193 Net realized and unrealized gains (losses) on investments ........................................... 227,856 208,034 378,933 456,828 687,111 Net investment income (loss): Fixed maturities ............................................................................................................................. 34,307 27,317 68,785 52,604 115,869 Short-term investments ................................................................................................................ 10 230 19 298 478 TS Hamilton Fund ......................................................................................................................... 1,948 2,858 3,584 4,594 10,673 Cash and cash equivalents ......................................................................................................... 4,195 3,987 8,489 8,590 16,287 Other ............................................................................................................................................... (6) 726 403 1,186 1,068 Interest and other ....................................................................................................................... 40,454 35,118 81,280 67,272 144,375 Management fees ....................................................................................................................... (15,643) (13,719) (30,112) (26,685) (55,153) Fixed maturities and short-term investments ........................................................................ (758) (636) (1,509) (1,201) (2,527) TS Hamilton Fund ...................................................................................................................... (14,885) (13,083) (28,603) (25,484) (52,626) Other expenses ........................................................................................................................... (371) (332) (699) (593) (1,201) Fixed maturities and short-term investments ........................................................................ (181) (105) (331) (209) (437) TS Hamilton Fund ...................................................................................................................... (190) (227) (368) (384) (764) Net investment income (loss) ................................................................................................. 24,440 21,067 50,469 39,994 88,021 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ......................................................................................................... 252,296 229,101 429,402 496,822 775,132 Net income (loss) attributable to non-controlling interest ....................................................... 111,021 80,371 194,515 180,765 263,359 Total net realized and unrealized gains (losses) on investments and net investment income (loss), net of non-controlling interest .............................................. $ 141,275 $ 148,730 $ 234,887 $ 316,057 $ 511,773 Fixed income, short-term investments and cash and cash equivalents return ................... $ 25,797 $ 61,644 $ 26,353 $ 125,404 $ 210,878 TS Hamilton Fund return(1) .......................................................................................................... $ 115,478 $ 87,086 $ 208,534 $ 190,653 300,895 Summary Consolidated Results Net Investment Return (1) Net of non-controlling interest performance incentive allocation.

10 June 30, 2026 December 31, 2025 ($ in thousands) Fair Value % of Total Weighted Average Credit Rating Fair Value % of Total Weighted Average Credit RatingFixed Maturity Trading Portfolio and Short-Term Investments(1) Fixed maturities U.S. government treasuries ...................................................................... $ 635,975 18% Aa1 $ 797,834 23% Aa1 U.S. states, territories and municipalities ............................................... 10,601 0% Aa2 12,960 0% Aa2 Non-U.S. sovereign governments and supranationals ......................... 108,784 3% Aa1 110,861 3% Aa1 Corporate ..................................................................................................... 1,732,278 51% A3 1,584,144 46% A3 Residential mortgage-backed securities - Agency ................................ 217,614 6% Aa1 365,650 11% Aa1 Residential mortgage-backed securities - Non-agency ....................... 56,722 2% Aa1 32,545 1% Aaa Commercial mortgage-backed securities - Non-agency ...................... 78,390 2% Aa1 94,698 3% Aa1 Other asset-backed securities .................................................................. 273,690 8% Aa1 239,851 7% Aa1 Total fixed maturities .................................................................................. 3,114,054 90% A1 3,238,543 94% Aa3 Short-term investments ................................................................................ 356,453 10% Aa1 200,459 6% Aa1 Total fixed maturities and short-term investments ................................. $ 3,470,507 100% Aa3 $ 3,439,002 100% Aa3 Fixed Maturity and Short-Term Investments Credit Quality Summary Investment grade .......................................................................................... 100% 100% Non-investment grade .................................................................................. 0% 0% Total .............................................................................................................. 100% 100% Fixed Maturity and Short-Term Investments - Trading Portfolio(2) June 30, 2026 December 31, 2025 Average credit quality ................................................................................... A1 Aa3 Average yield to maturity ............................................................................. 4.7% 4.1% Book yield ....................................................................................................... 4.5% 4.3% Expected average duration (in years) ....................................................... 4.0 3.4 (1) Includes $356.4 million and $199.0 million of short-term investments, at June 30, 2026 and December 31, 2025, respectively, not managed by our external investment managers. (2) Fixed income portfolio managed by our external investment managers only. Summary Consolidated Results Fixed Maturity and Short-Term Investments

11 Three Months Ended June 30, 2026 Three Months Ended June 30, 2025 ($ in thousands) International Bermuda Total International Bermuda Total Gross premiums written ........................................................................ $ 420,073 $ 410,968 $ 831,041 $ 344,799 $ 367,227 $ 712,026 Net premiums written ............................................................................. 322,843 298,852 621,695 258,089 298,225 556,314 Net premiums earned ............................................................................ 302,623 283,384 586,007 253,209 257,954 511,163 Third party fee income ........................................................................... 1,820 2,084 3,904 3,832 1,182 5,014 Losses and loss adjustment expenses ............................................... 174,274 187,215 361,489 124,733 145,195 269,928 Acquisition costs ..................................................................................... 80,287 65,136 145,423 65,683 57,132 122,815 Other underwriting expenses ................................................................ 40,758 13,129 53,887 39,507 16,468 55,975 Underwriting income (loss) ................................................................... $ 9,124 $ 19,988 $ 29,112 $ 27,118 $ 40,341 $ 67,459 Key Ratios: Attritional loss ratio - current year ........................................................ 51.1 % 55.7 % 53.3 % 51.9 % 54.2 % 53.0 % Attritional loss ratio - prior year development .................................... (4.6) % 4.6 % (0.1) % (3.0) % 2.0 % (0.5) % Catastrophe loss ratio - current year ................................................... 11.1 % 4.3 % 7.8 % 0.6 % 3.2 % 1.9 % Catastrophe loss ratio - prior year development ............................... 0.0 % 1.5 % 0.7 % (0.2) % (3.1) % (1.6) % Loss and loss adjustment expense ratio ............................................ 57.6 % 66.1 % 61.7 % 49.3 % 56.3 % 52.8 % Acquisition cost ratio .............................................................................. 26.5 % 23.0 % 24.8 % 25.9 % 22.1 % 24.0 % Other underwriting expense ratio ......................................................... 12.9 % 3.9 % 8.5 % 14.1 % 5.9 % 10.0 % Combined ratio ........................................................................................ 97.0 % 93.0 % 95.0 % 89.3 % 84.3 % 86.8 % Segment Results Consolidated Underwriting Results

12 Six Months Ended June 30, 2026 Six Months Ended June 30, 2025 ($ in thousands) International Bermuda Total International Bermuda Total Gross premiums written ......................................................................... $ 862,982 $ 908,170 $ 1,771,152 $ 714,757 $ 840,575 $ 1,555,332 Net premiums written .............................................................................. 610,280 665,075 1,275,355 487,063 673,126 1,160,189 Net premiums earned ............................................................................. 593,414 563,108 1,156,522 493,775 516,316 1,010,091 Third party fee income ............................................................................ 4,367 6,288 10,655 8,164 1,512 9,676 Losses and loss adjustment expenses ................................................ 338,129 348,145 686,274 270,405 394,758 665,163 Acquisition costs ...................................................................................... 161,491 128,438 289,929 128,473 111,223 239,696 Other underwriting expenses ................................................................ 82,057 22,222 104,279 75,130 30,579 105,709 Underwriting income (loss) .................................................................... $ 16,104 $ 70,591 $ 86,695 $ 27,931 $ (18,732) $ 9,199 Key Ratios: Attritional loss ratio - current year ......................................................... 53.0 % 54.9 % 53.9 % 52.0 % 53.0 % 52.5 % Attritional loss ratio - prior year development ..................................... (1.7) % 4.1 % 1.1 % (3.3) % (0.1) % (1.7) % Catastrophe loss ratio - current year .................................................... 5.7 % 2.1 % 4.0 % 6.2 % 26.9 % 16.8 % Catastrophe loss ratio - prior year development ................................ 0.0 % 0.7 % 0.3 % (0.1) % (3.3) % (1.7) % Loss and loss adjustment expense ratio ............................................. 57.0 % 61.8 % 59.3 % 54.8 % 76.5 % 65.9 % Acquisition cost ratio ............................................................................... 27.2 % 22.8 % 25.1 % 26.0 % 21.5 % 23.7 % Other underwriting expense ratio ......................................................... 13.1 % 2.8 % 8.1 % 13.6 % 5.6 % 9.5 % Combined ratio ........................................................................................ 97.3 % 87.4 % 92.5 % 94.4 % 103.6 % 99.1 % Segment Results Consolidated Underwriting Results

13 Three Months Ended Six Months Ended Year Ended June 30, March 31, December 31, September 30, June 30, June 30, June 30, December 31, ($ in thousands) 2026 2026 2025 2025 2025 2026 2025 2025 Gross premiums written ............................................. $ 831,041 $ 940,110 $ 668,968 $ 698,845 $ 712,026 $ 1,771,152 $ 1,555,332 $ 2,923,145 Net premiums written ................................................. 621,695 653,659 548,373 578,981 556,314 1,275,355 1,160,189 2,287,543 Net premiums earned ................................................ 586,007 570,515 576,686 522,999 511,163 1,156,522 1,010,091 2,109,776 Third party fee income ............................................... 3,904 6,750 12,756 4,169 5,014 10,655 9,676 26,601 Losses and loss adjustment expenses ................... 361,489 324,785 314,646 278,712 269,928 686,274 665,163 1,258,521 Acquisition costs ......................................................... 145,423 144,507 142,181 125,412 122,815 289,929 239,696 507,290 Other underwriting expenses .................................... 53,887 50,392 57,079 58,955 55,975 104,279 105,709 221,743 Underwriting income (loss) ........................................ $ 29,112 $ 57,581 $ 75,536 $ 64,089 $ 67,459 $ 86,695 $ 9,199 $ 148,823 Key Ratios: Attritional loss ratio - current year ............................ 53.3 % 54.5 % 56.5 % 55.4 % 53.0 % 53.9 % 52.5 % 54.4 % Attritional loss ratio - prior year development ......... (0.1) % 2.4 % (3.1) % (2.1) % (0.5) % 1.1 % (1.7) % (2.2) % Catastrophe loss ratio - current year ....................... 7.8 % 0.0 % 1.4 % 0.0 % 1.9 % 4.0 % 16.8 % 8.4 % Catastrophe loss ratio - prior year development .... 0.7 % 0.0 % (0.2) % 0.0 % (1.6) % 0.3 % (1.7) % (0.9) % Loss and loss adjustment expense ratio ................. 61.7 % 56.9 % 54.6 % 53.3 % 52.8 % 59.3 % 65.9 % 59.7 % Acquisition cost ratio .................................................. 24.8 % 25.3 % 24.7 % 24.0 % 24.0 % 25.1 % 23.7 % 24.0 % Other underwriting expense ratio ............................. 8.5 % 7.6 % 7.7 % 10.5 % 10.0 % 8.1 % 9.5 % 9.2 % Combined ratio ............................................................ 95.0 % 89.8 % 87.0 % 87.8 % 86.8 % 92.5 % 99.1 % 92.9 % Gross premiums written Property ........................................................................ $ 183,986 $ 248,234 $ 76,203 $ 134,626 $ 207,488 $ 432,221 $ 485,091 $ 695,920 Casualty ....................................................................... 409,517 397,430 379,830 377,483 322,446 806,947 637,542 1,394,855 Specialty ....................................................................... 237,538 294,446 212,935 186,736 182,092 531,984 432,699 832,370 Total ............................................................................ $ 831,041 $ 940,110 $ 668,968 $ 698,845 $ 712,026 $ 1,771,152 $ 1,555,332 $ 2,923,145 Net premiums earned Property ........................................................................ $ 117,868 $ 126,825 $ 125,109 $ 130,248 $ 124,019 $ 244,693 $ 265,192 $ 520,549 Casualty ....................................................................... 291,401 265,978 261,562 243,997 232,047 557,379 449,719 955,278 Specialty ....................................................................... 176,738 177,712 190,015 148,754 155,097 354,450 295,180 633,949 Total ............................................................................ $ 586,007 $ 570,515 $ 576,686 $ 522,999 $ 511,163 $ 1,156,522 $ 1,010,091 $ 2,109,776 Segment Results 5Q Consolidated Underwriting Results - Group

14 Three Months Ended Six Months Ended Year Ended June 30, March 31, December 31, September 30, June 30, June 30, June 30, December 31, ($ in thousands) 2026 2026 2025 2025 2025 2026 2025 2025 Gross premiums written ............................................. $ 420,073 $ 442,908 $ 422,345 $ 379,957 $ 344,799 $ 862,982 $ 714,757 $ 1,517,060 Net premiums written ................................................. 322,843 287,436 340,588 304,410 258,089 610,280 487,063 1,132,061 Net premiums earned ................................................ 302,623 290,791 309,299 252,302 253,209 593,414 493,775 1,055,377 Third party fee income ............................................... 1,820 2,546 1,726 2,137 3,832 4,367 8,164 12,027 Losses and loss adjustment expenses ................... 174,274 163,855 166,998 133,895 124,733 338,129 270,405 571,298 Acquisition costs ......................................................... 80,287 81,204 81,195 67,007 65,683 161,491 128,473 276,676 Other underwriting expenses .................................... 40,758 41,299 50,388 41,703 39,507 82,057 75,130 167,221 Underwriting income (loss) ........................................ $ 9,124 $ 6,979 $ 12,444 $ 11,834 $ 27,118 $ 16,104 $ 27,931 $ 52,209 Key Ratios: Attritional loss ratio - current year ............................ 51.1 % 54.9 % 56.3 % 55.3 % 51.9 % 53.0 % 52.0 % 54.0 % Attritional loss ratio - prior year development ......... (4.6) % 1.4 % (2.3) % (2.2) % (3.0) % (1.7) % (3.3) % (2.8) % Catastrophe loss ratio - current year ....................... 11.1 % 0.0 % 0.0 % 0.0 % 0.6 % 5.7 % 6.2 % 2.9 % Catastrophe loss ratio - prior year development .... 0.0 % 0.0 % 0.0 % 0.0 % (0.2) % 0.0 % (0.1) % 0.0 % Loss and loss adjustment expense ratio ................. 57.6 % 56.3 % 54.0 % 53.1 % 49.3 % 57.0 % 54.8 % 54.1 % Acquisition cost ratio .................................................. 26.5 % 27.9 % 26.3 % 26.6 % 25.9 % 27.2 % 26.0 % 26.2 % Other underwriting expense ratio ............................. 12.9 % 13.3 % 15.7 % 15.7 % 14.1 % 13.1 % 13.6 % 14.7 % Combined ratio ............................................................ 97.0 % 97.5 % 96.0 % 95.4 % 89.3 % 97.3 % 94.4 % 95.0 % Gross premiums written Property ........................................................................ $ 61,292 $ 54,496 $ 55,276 $ 63,894 $ 63,871 $ 115,789 $ 118,397 $ 237,568 Casualty ....................................................................... 175,394 166,577 185,152 167,107 140,441 341,971 276,003 628,262 Specialty ....................................................................... 183,387 221,835 181,917 148,956 140,487 405,222 320,357 651,230 Total ............................................................................ $ 420,073 $ 442,908 $ 422,345 $ 379,957 $ 344,799 $ 862,982 $ 714,757 $ 1,517,060 Net premiums earned Property ........................................................................ $ 48,191 $ 50,586 $ 47,772 $ 47,813 $ 43,706 $ 98,777 $ 89,410 $ 184,995 Casualty ....................................................................... 115,845 99,880 104,188 91,841 89,233 215,725 179,801 375,831 Specialty ....................................................................... 138,587 140,325 157,339 112,648 120,270 278,912 224,564 494,551 Total ............................................................................ $ 302,623 $ 290,791 $ 309,299 $ 252,302 $ 253,209 $ 593,414 $ 493,775 $ 1,055,377 Segment Results 5Q Underwriting Results - International

15 Three Months Ended Six Months Ended Year Ended June 30, March 31, December 31, September 30, June 30, June 30, June 30, December 31, ($ in thousands) 2026 2026 2025 2025 2025 2026 2025 2025 Gross premiums written ............................................. $ 410,968 $ 497,202 $ 246,623 $ 318,888 $ 367,227 $ 908,170 $ 840,575 $ 1,406,085 Net premiums written ................................................. 298,852 366,223 207,785 274,571 298,225 665,075 673,126 1,155,482 Net premiums earned ................................................ 283,384 279,724 267,387 270,697 257,954 563,108 516,316 1,054,399 Third party fee income ............................................... 2,084 4,204 11,030 2,032 1,182 6,288 1,512 14,574 Losses and loss adjustment expenses ................... 187,215 160,930 147,648 144,817 145,195 348,145 394,758 687,223 Acquisition costs ......................................................... 65,136 63,303 60,986 58,405 57,132 128,438 111,223 230,614 Other underwriting expenses .................................... 13,129 9,093 6,691 17,252 16,468 22,222 30,579 54,522 Underwriting income (loss) ........................................ $ 19,988 $ 50,602 $ 63,092 $ 52,255 $ 40,341 $ 70,591 $ (18,732) $ 96,614 Key Ratios: Attritional loss ratio - current year ............................ 55.7 % 53.9 % 56.7 % 55.6 % 54.2 % 54.9 % 53.0 % 54.6 % Attritional loss ratio - prior year development ......... 4.6 % 3.6 % (4.1) % (2.1) % 2.0 % 4.1 % (0.1) % (1.6) % Catastrophe loss ratio - current year ....................... 4.3 % 0.0 % 3.0 % 0.0 % 3.2 % 2.1 % 26.9 % 13.9 % Catastrophe loss ratio - prior year development .... 1.5 % 0.0 % (0.4) % 0.0 % (3.1) % 0.7 % (3.3) % (1.7) % Loss and loss adjustment expense ratio ................. 66.1 % 57.5 % 55.2 % 53.5 % 56.3 % 61.8 % 76.5 % 65.2 % Acquisition cost ratio .................................................. 23.0 % 22.6 % 22.8 % 21.6 % 22.1 % 22.8 % 21.5 % 21.9 % Other underwriting expense ratio ............................. 3.9 % 1.7 % (1.6) % 5.6 % 5.9 % 2.8 % 5.6 % 3.8 % Combined ratio ............................................................ 93.0 % 81.8 % 76.4 % 80.7 % 84.3 % 87.4 % 103.6 % 90.9 % Gross premiums written Property ........................................................................ $ 122,694 $ 193,738 $ 20,927 $ 70,732 $ 143,617 $ 316,432 $ 366,694 $ 458,352 Casualty ....................................................................... 234,123 230,853 194,678 210,376 182,005 464,976 361,539 766,593 Specialty ....................................................................... 54,151 72,611 31,018 37,780 41,605 126,762 112,342 181,140 Total ............................................................................ $ 410,968 $ 497,202 $ 246,623 $ 318,888 $ 367,227 $ 908,170 $ 840,575 $ 1,406,085 Net premiums earned Property ........................................................................ $ 69,677 $ 76,239 $ 77,337 $ 82,435 $ 80,313 $ 145,916 $ 175,782 $ 335,554 Casualty ....................................................................... 175,556 166,098 157,374 152,156 142,814 341,654 269,918 579,447 Specialty ....................................................................... 38,151 37,387 32,676 36,106 34,827 75,538 70,616 139,398 Total ............................................................................ $ 283,384 $ 279,724 $ 267,387 $ 270,697 $ 257,954 $ 563,108 $ 516,316 $ 1,054,399 Segment Results 5Q Underwriting Results - Bermuda

16 Region Peril Probability of Exceedance Group Net PML ($m)(1) % of Shareholders' Equity Florida U.S. Hurricane 1 in 100 $ 215.2 7.5 % Northeast U.S. Hurricane 1 in 100 211.5 7.4 % Gulf (TX - AL) U.S. Hurricane 1 in 100 190.5 6.7 % California Earthquake 1 in 250 299.2 10.5 % Pacific Northwest Earthquake 1 in 250 148.1 5.2 % (1) Group Net PML is a measure of loss across all Hamilton entities net of recoveries from various reinsurance contracts and catastrophe bonds we purchase to mitigate catastrophe losses and net of estimated reinstatement premium to renew coverage. Our peak natural catastrophe PMLs are derived using vendor catastrophe models that serve as a baseline and proprietary tools that allow us to make a number of significant adjustments. Adjustments are informed by periodic evaluation of vendor models and risk learning from comparing actual and modeled losses of catastrophe events, thus allowing for a view of risk that we believe is materially more complete and appropriate to the current risk landscape. Our peak natural catastrophe PMLs are measured using stochastic models that use hypothetical events of perils such as hurricanes and earthquakes. We define PML as the anticipated loss, taking into account contract terms and limits, caused by a single catastrophe affecting a broad contiguous geographical area, and are expressed at refine "return periods", such as "100-year events" and "250-year events". For example, a 100-year PML is the estimated loss to the current in-force portfolio from a single event which has a 1% probability of being exceeded in a twelve month period. Due to the uncertain nature of catastrophes and the hypothetical nature of vendor catastrophe models we use for estimating losses, there is no assurance that actual losses we experience within a time period will match the modeled PML. This approach to measuring catastrophe losses, however, is consistent with the best practice in the industry and employed by almost all of our peers. Other Information Modeled Exposure to Catastrophe Losses (PML) Net Probable Maximum Loss ("PML") as of July 1, 2026 ($ in millions)

17 Other Information Non-GAAP Measures We present our results of operations in a way that we believe will be the most meaningful and useful to investors, analysts, rating agencies and others who use our financial information to evaluate our performance. Some of the measurements that management uses to assess our operating results are considered non-GAAP financial measures under Regulation G and Item 10(e) of Regulation S-K, each promulgated by the SEC. We believe that these non- GAAP financial measures, which may be defined and calculated differently by other companies, help explain and enhance the understanding of our results of operations. However, these measures should not be viewed as a substitute for those determined in accordance with U.S. GAAP. Where appropriate, reconciliations of our non-GAAP measures to the most directly comparable GAAP financial measures are included below. Operating Income (Loss) Attributable to Common Shareholders, Operating Income (Loss) Attributable to Common Shareholders per Common Share - Diluted and Operating Return on Average Common Shareholders' Equity - Annualized Operating income (loss) attributable to common shareholders, as used herein, differs from net income (loss) and other comprehensive income (loss) attributable to common shareholders, which we believe is the most directly comparable GAAP measure, by the exclusion of net realized and unrealized gains and losses on fixed maturity and short term investments, and net foreign exchange gains and losses. We also use operating income (loss) attributable to common shareholders to calculate operating income (loss) attributable to common shareholders per common share - diluted and operating return on average common shareholders' equity - annualized. We believe that operating income (loss) attributable to common shareholders, operating income (loss) attributable to common shareholders per common share - diluted and operating return on average common shareholders' equity - annualized are meaningful and useful to investors, analysts, rating agencies and others who use our financial information to evaluate our performance. The following tables are a reconciliation of: net income (loss) and other comprehensive income (loss) attributable to common shareholders to operating income (loss) attributable to common shareholders; net income (loss) and other comprehensive income (loss) attributable to common shareholders per common share - diluted to operating income (loss) attributable to common shareholders per common share - diluted; and return on average common shareholders' equity - annualized to operating return on average common shareholders' equity - annualized. Comparative information for the prior periods presented have been updated to conform to the current methodology and presentation.

18 Return on average common shareholders' equity - annualized ............................................... 20.6 % 30.2 % 19.6 % 22.0 % 22.4 % Adjustment for: Net realized (gains) losses on investments - Fixed maturity and short-term investments(1) ................................................................................................................ 0.8 % (0.2) % 0.2 % (0.1) % (0.3) % Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1) ................................................................................................................ 0.9 % (4.6) % 3.3 % (5.2) % (2.8) % Net foreign exchange (gains) losses ............................................................................................ 0.4 % 0.7 % (0.2) % 0.6 % 0.2 % Operating return on average common shareholders' equity - annualized .............................. 22.7 % 26.1 % 22.9 % 17.3 % 19.5 % Other Information Non-GAAP Measures Net income (loss) and other comprehensive income (loss) attributable to common shareholders per common share - diluted ................................................................... $ 1.42 $ 1.79 $ 2.73 $ 2.56 $ 5.55 Adjustment for: Net realized (gains) losses on investments - Fixed maturity and short-term investments(1) ................................................................................................................ 0.05 (0.01) 0.02 (0.01) (0.07) Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1) ................................................................................................................ 0.06 (0.27) 0.46 (0.60) (0.70) Net foreign exchange (gains) losses ............................................................................................ 0.03 0.04 (0.01) 0.06 0.06 Operating income (loss) attributable to common shareholders per common share - diluted .................................................................................................................. $ 1.56 $ 1.55 $ 3.20 $ 2.01 $ 4.84 Three Months Ended June 30, Six Months Ended June 30, Year Ended ($ in thousands, except per share amounts) 2026 2025 2026 2025 2025 Net income (loss) and other comprehensive income (loss) attributable to common shareholders .................................................................................................................... $ 143,782 $ 187,415 $ 277,320 $ 268,288 $ 576,670 Adjustment for: Net realized (gains) losses on investments - Fixed maturity and short-term investments(1) ................................................................................................................ 5,241 (1,343) 2,332 (867) (7,369) Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1) ................................................................................................................ 6,529 (28,782) 47,171 (63,269) (72,771) Net foreign exchange (gains) losses ............................................................................................ 2,629 4,513 $ (1,905) $ 7,039 $ 5,985 Operating income (loss) attributable to common shareholders ............................................... $ 158,181 $ 161,803 $ 324,918 $ 211,191 $ 502,515 Operating Income (Loss) Attributable to Common Shareholders, Operating Income (Loss) Attributable to Common Shareholders per Common Share - Diluted and Operating Return on Average Common Shareholders' Equity - Annualized (continued) (1) Fixed income portfolio managed by our external investment managers only

19 Underwriting Income (Loss) We calculate underwriting income (loss) on a pre-tax basis as net premiums earned less losses and loss adjustment expenses, acquisition costs and other underwriting expenses (net of third party fee income). We believe that this measure of our performance focuses on the core fundamental performance of the Company’s reportable segments in any given period and is not distorted by investment market conditions, corporate expense allocations or income tax effects. The table below reconciles underwriting income (loss) to net income (loss), the most directly comparable GAAP financial measure: Three Months Ended June 30, Six Months Ended June 30, Year Ended ($ in thousands) 2026 2025 2026 2025 2025 Underwriting income (loss) ............................................................................................................. $ 29,112 $ 67,459 $ 86,695 $ 9,199 $ 148,823 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ......................................................................................................... 252,296 229,101 429,402 496,822 775,132 Net foreign exchange gains (losses) ............................................................................................ (2,629) (4,513) 1,905 (7,039) (5,985) Corporate expenses ........................................................................................................................ (13,044) (12,853) (24,116) (25,821) (57,167) Amortization of intangible assets .................................................................................................. (3,700) (4,004) (7,720) (7,895) (15,709) Interest expense .............................................................................................................................. (4,762) (4,729) (9,538) (10,331) (20,189) Income tax (expense) benefit ........................................................................................................ (2,470) (2,675) (4,793) (5,882) 15,124 Net income (loss), prior to non-controlling interest ..................................................................... $ 254,803 $ 267,786 $ 471,835 $ 449,053 $ 840,029 Other Information Non-GAAP Measures Third Party Fee Income Third party fee income includes income that is incremental and/or directly attributable to our underwriting operations. It is primarily comprised of performance and management fees earned by the Bermuda segment that were generated by our third party capital manager, Ada Capital Management Limited, and fees earned by the International segment for management services provided to consortia and third party syndicates. We believe that this measure is a relevant component of our underwriting income (loss), with other income (loss) being the most directly comparable GAAP financial measure. Three Months Ended June 30, Six Months Ended June 30, Year Ended ($ in thousands) 2026 2025 2026 2025 2025 Third party fee income .................................................................................................................... $ 3,904 $ 5,014 $ 10,655 $ 9,676 $ 26,601 Other income (loss) ......................................................................................................................... $ 3,904 $ 5,014 $ 10,655 $ 9,676 $ 26,601

20 Three Months Ended June 30, Six Months Ended June 30, Year Ended ($ in thousands) 2026 2025 2026 2025 2025 Other underwriting expenses ......................................................................................................... $ 53,887 $ 55,975 $ 104,279 $ 105,709 $ 221,743 Corporate expenses ........................................................................................................................ 13,044 12,853 24,116 25,821 57,167 General and administrative expenses .......................................................................................... $ 66,931 $ 68,828 $ 128,395 $ 131,530 $ 278,910 Other Information Non-GAAP Measures Other Underwriting Expenses Other underwriting expenses include those general and administrative expenses that are incremental and/or directly attributable to our underwriting operations. While this measure is presented in Note 8, Segment Reporting in the unaudited condensed consolidated financial statements, it is considered a non-GAAP financial measure when presented elsewhere. Corporate expenses include holding company costs necessary to support our reportable segments. As these costs are not incremental and/or directly attributable to our underwriting operations, these costs are excluded from other underwriting expenses, and therefore, underwriting income (loss). General and administrative expenses, the most comparable GAAP financial measure to other underwriting expenses, also includes corporate expenses. The table below reconciles other underwriting expenses to general and administrative expenses, the most directly comparable GAAP financial measure: Other Underwriting Expense Ratio Other Underwriting Expense Ratio is a measure of the other underwriting expenses (net of third party fee income) incurred by the Company and is expressed as a percentage of net premiums earned. Loss Ratio Attritional Loss Ratio – current year is the attritional losses incurred by the company relating to the current year divided by net premiums earned. Attritional Loss Ratio – prior year development is the attritional losses incurred by the company relating to prior years divided by net premiums earned. Catastrophe Loss Ratio – current year is the catastrophe losses incurred by the company relating to the current year divided by net premiums earned. Catastrophe Loss Ratio – prior year development is the catastrophe losses incurred by the company relating to prior years divided by net premiums earned. Combined Ratio Combined Ratio is a measure of our underwriting profitability and is expressed as the sum of the loss and loss adjustment expense ratio, acquisition cost ratio and other underwriting expense ratio. A combined ratio under 100% indicates an underwriting profit, while a combined ratio over 100% indicates an underwriting loss.

Investor Presentation 2Q 2026 Hamilton Insurance Group, Ltd.

2 Special Note Regarding Forward-Looking Statements This presentation includes "forward looking statements" pursuant to the safe harbor provisions of the U.S. Private Securities Litigation Reform Act of 1995. Forward-looking statements can be identified by the use of terms such as "believes," "expects," "may," "will," "target," "should," "could," " would," "seeks," "intends," "plans," "contemplates," "estimates," "forecasts," or "anticipates," or similar expressions which concern our strategy, plans, projections or intentio ns. These forward-looking statements appear in a number of places and relate to matters such as our industry, growth strategy, goals and expectations concerning our market position, fu ture operations, margins, profitability, capital expenditures, liquidity and capital resources, business plans (including syndicate capacity forecasts) , and other financial and operating information. By their nature, forward-looking statements: speak only as of the date they are made; are not statements of historical fact or guarantees of future performance; and are subject to risks, uncertainties, assumptions, or changes in circumstances that are difficult to predict or quantify. Our expectations , beliefs, and projections are expressed in good faith and we believe there is a reasonable basis for them. However, there can be no assurance that management’s expectations, belie fs and projections will be achieved and actual results may vary materially from what is expressed in or indicated by the forward-looking statements. There are a number of risks, uncertainties, and other important factors that could cause our actual results to differ materially from the forward -looking statements contained herein. Such risks, uncertainties, and other important factors include, among others, the risks, uncertainties and factors se t forth in "Risk Factors" and "Management’s Discussion and Analysis of Financial Condition and Results of Operations" included in our Annual Report on Form 10 -K for the year ended December 31, 2025, our other subsequent periodic reports filed with the Securities and Exchange Commission and the following: • challenges from competitors, including those arising from industry consolidation, alternative capital and technological advancements, including the increasing use of advanced analytics and artificial intelligence; • unpredictable events, including natural catastrophes and man made disasters, global climate change and emerging claim, litigation and coverage issues that may increase loss severity or expand coverage obligations; • our ability, or that of the third parties on which we rely, to ensure reserves are adequate to cover actual losses and to accurately assess underwriting risk, models, assumptions, data quality and the pricing of risks, particularly in long tail, low frequency or emerging lines of business; • our ability to defend and protect our intellectual property rights, including our proprietary technology platforms and data, to comply with obligations under license and technology agreements or to obtain or renew licenses to technology or data on reasonable terms; • the impact of risks associated with human error, misconduct or fraud, model uncertainty, cybersecurity threats such as cyber attacks and security breaches, misuse of artificial intelligence and our reliance on third party information technology systems that may fail, be disrupted or require replacement; • our ability to secure necessary credit facilities, letters of credit or other forms of financing or collateral on favorable terms or at all; • our limited financial and operational flexibility due to covenants and other restrictions in our existing or future credit facilities and debt arrangements; • our exposure to the credit risk of insurance and reinsurance intermediaries on which we rely for the collection of premiums and payment of claims; • our failure to pay claims in a timely manner, significant reserve strengthening, or the need to sell investments under unfavorable market or other conditions in order to meet liquidity requirements; • downgrades, potential downgrades or other negative actions by rating agencies, including changes in rating agency methodologies; • our ability to manage risks associated with adverse macroeconomic conditions, geopolitical instability and global events, including current or anticipated military conflicts, public health crises, terrorism, sanctions, inflation, rising interest rates, energy price volatility and other disruptions;

3 Special Note Regarding Forward-Looking Statements There may be other factors that could cause our actual results to differ materially from the forward-looking statements. You should evaluate all forward-looking statements made herein in the context of these risks and uncertainties. You should read this information completely and with the understanding that actual future results may be materially different from expectations. We caution you that the risks, uncertainties, and other factors referenced above may not contain all of the risks, uncertainties and other factors th at are important to you. In addition, we cannot assure you that we will realize the results, benefits, or developments that we expect or anticipate or, even if substantially realized, that they will result in the consequences or affect us or our business in the way expected. All forward-looking statements contained herein apply only as of the date hereof and are expressly qualified in their entirety by these cautionary statements. We undertake no obligation to publicly update or revise any forward-looking statements to reflect subsequent events or circumstances. • the cyclical nature of the insurance and reinsurance business, which may result in declines in pricing and more competitive terms and conditions; • our results of operations fluctuating significantly from period to period and not being indicative of our long term prospects; • our ability to execute our strategy and to adapt our business and strategic plans in response to changing market, regulatory and competitive conditions; • our dependence on key executives and other personnel, including the potential loss of Bermudian or other critical personnel, and our ability to attract and retain qualified employees in highly competitive labor markets; • foreign operational risks, including foreign currency risk, political instability, regulatory uncertainty and differing legal regimes in jurisdictions where we operate; • our ability to identify, execute and integrate growth opportunities, including acquisitions or other strategic transactions, and to realize the anticipated benefits of such initiatives; • risks arising from our management of alternative reinsurance platforms and vehicles for third party investors; • our inability to control the asset allocation, investment decisions or performance of the Two Sigma Hamilton Fund, LLC (the “TS Hamilton Fund” or “TSHF”) and our limited ability to withdraw capital from the TS Hamilton Fund; • conflicts of interest, governance, operational or regulatory risks involving Two Sigma Investments, LP (“Two Sigma”), the TS Hamilton Fund or their respective affiliates that could adversely affect investment performance or our business; • the historical performance of Two Sigma or the TS Hamilton Fund not being indicative of future performance or our future results; • risks associated with our investment strategy, including the use of leverage, derivatives, illiquid assets and concentration risk, which may be greater than those faced by some of our competitors; • our potentially becoming subject to additional or increased taxation, including U.S. federal income tax, Bermuda tax or other taxes, as a result of changes in tax laws, interpretations or our operations; • the potential classification of us or our subsidiaries as a passive foreign investment company or becoming subject to U.S. withholding and information reporting requirements under the U.S. Foreign Account Tax Compliance Act; • our ability to compete effectively in a highly regulated industry in light of new or changing domestic or international laws and regulations, including accounting standards and evolving regulatory interpretations; • the suspension, limitation or revocation of licenses or approvals required by our insurance and reinsurance subsidiaries; • significant legal, regulatory or governmental proceedings or investigations; • restrictions on our insurance and reinsurance subsidiaries’ ability to pay dividends or make other distributions to us; • challenges and costs associated with compliance with public company disclosure, governance and internal control requirements; • the limited ability of investors to influence corporate matters due to our multi class share structure and the voting provisions in our Bye laws; • the risk that anti takeover provisions in our Bye laws or Bermuda law could discourage, delay or prevent a change in control, even if beneficial to shareholders; and • difficulties investors may face in enforcing judgments or protecting their interests against us or our directors and officers.

Introduction to Hamilton

5 Highly Experienced Leadership Team Introduction to Hamilton Fostering an inclusive, collaborative and entrepreneurial culture Executive leadership Experienced board of directors Pina Albo Group CEO 30+ Years Former: Munich Re Craig Howie Group CFO 35+ Years Former: Everest Raymond Karrenbauer Group CIO 25+ Years Former: Cyber AB Daniel Fisher Group Head of HR, Communications & Culture 25+ Years Former: Munich Re Gemma Carreiro General Counsel 20+ Years Former: PartnerRe Alex Baker CEO, Hamilton Global Specialty 20+ Years Former: Chubb Insurance Adrian Daws CEO, Hamilton Re 20+ Years Former: CNA Hardy Anita Kuchma CEO, Hamilton Select 35+ Years Former: Munich Re Tim Duffin Group CUO 25+ Years Former: Platinum Russ Buckley Group CRO 30+ Years Former: Old Republic

6Introduction to Hamilton This declares our promise to everyone we interact with. We believe we are enriched by one another’s attitudes, experiences and knowledge. Our colleagues share a passion for service and results. We know that what we do each day is meaningful – to our customers and our business. Highly collaborative Service orientedOpen, diverse and inclusive Expertise

7 Hamilton – Overview and Results Introduction to Hamilton $2.9B FY 2025 $1.8B 1H 2026 Gross Premiums Written (GPW) $149m FY 2025 $87m 1H 2026 Underwriting Income 92.9% FY 2025 92.5% 1H 2026 Combined Ratio $6.1B 2Q 2026 Cash & Invested Assets $2.9B 2Q 2026 Shareholders’ Equity $577m FY 2025 $277m 1H 2026 Net Income R e p o rt in g S e g m e n ts International 2025 GPW $1.5B Bermuda 2025 GPW $1.4B Hamilton Global Specialty (London & Dublin) Hamilton Select (USA) Hamilton Re (Bermuda) O p e ra ti n g P la tf o rm s 20 25 S e g m e n t C o m b in e d R a ti o 95.0% 90.9% Financial Strength Ratings A (Stable) 1 AM Best A (Stable) 2 KBRA A- (Stable) 3 Fitch (1) AM Best ratings of Hamilton Re, Ltd., Hamilton Insurance DAC and Hamilton Select, (2) KBRA ratings of Hamilton Re, Ltd., (3) Fitch ratings of Hamilton Re, Ltd. and Hamilton Insurance DAC Annual Segmental Results Group Financial Highlights

8 Diversified and Well Scaled Underwriting Platforms Facilitate Cycle Management Introduction to Hamilton Diversified by Insurance / Reinsurance, Class of Business, and Segment / Geography Insurance 50% Reinsurance 50% Insurance / Reinsurance Property 24% Casualty 48% Specialty 28% Class of Business International 52% Bermuda 48% Business Segments 2025 Gross Premiums Written of $2.9 Billion Global presence: Bermuda, Ireland, UK, US

9 Hamilton Group – Strategic Growth and Sustainable Underwriting Profitability Introduction to Hamilton Double digit top line growth with bottom line improvement 68% 66% 54% 58% 60% 66% 59% 38% 37% 36% 33% 33% 33% 33% 106% 103% 90% 91% 93% 99% 93% 2021 2022 2023 2024 2025 1H 2025 1H 2026 $1,447 $1,647 $1,951 $2,423 $2,923 $1,555 $1,771 2021 2022 2023 2024 2025 1H 2025 1H 2026 Hamilton Group - Gross Premiums Written ($’m) Hamilton Group - Combined Ratio(2) Loss Ratio Expense Ratio (3) (1) Compound annual growth rate, (2) Numbers may not add due to rounding, (3) Combined ratio excluding the Ukraine Conflict was 96%

Segment Results

11 International Segment: Market Leading Writer of Specialty (Re)Insurance Business Specialty insurance products written in Lloyd’s, Hamilton Insurance DAC, HMGA Americas & Hamilton Select Segment Results 16% 41% 43% Property Casualty Specialty 2025 GPW Business Mix 88% 12% Insurance Reinsurance $1.5B Hamilton Select $157m / 10% Hamilton Global Specialty • Lloyd’s Syndicate 4000 and Hamilton Insurance DAC (Ireland) • Ability to offer both Lloyd’s and company paper increases access to business • Longstanding client & broker relationships fuel growth in core E&S markets • $1.4 billion of gross premiums written in 2025 • Limited legacy exposures prior to 2019 Hamilton Select • U.S. domiciled surplus lines carrier specializing in small to midsize, hard-to-place lines of business Highlights

12 International Segment: Opportunities for Growth Remain in Transitioning Market Environment Segment Results Results reflect the diversified, lower volatility portfolio we have built over time 63% 54% 52% 56% 54% 55% 57% 44% 43% 43% 39% 41% 40% 40% 108% 97% 95% 96% 95% 94% 97% 2021 2022 2023 2024 2025 1H 2025 1H 2026 (3) $892 $933 $1,106 $1,308 $1,517 $715 $863 2021 2022 2023 2024 2025 1H 2025 1H 2026 International Segment - Gross Premiums Written ($’m) International Segment - Combined Ratio(2) Loss Ratio Expense Ratio (1) Compound annual growth rate, (2) Numbers may not add due to rounding, (3) Combined ratio excluding the Ukraine Conflict was 93%

13 33% 54% 13% Property Casualty Specialty Bermuda Segment: Well Diversified Writer of Property, Casualty and Specialty Classes Underwriting-focused operation with strong foundation to trade through the cycle Segment Results 2025 GPW Business Mix Hamilton Re • Established, scaled platform with broad, diversified client base • Demonstrated underwriting profitability through portfolio optimization and thoughtful cycle management • Strategic growth enhanced by diversified product offering • Reinsurance business written in both Bermuda and US • Clear, consistent appetite and responsive service rewarded by clients and brokers • Data-driven approach supports underwriting and operational efficiencies Highlights 9% 91% Insurance Reinsurance $1.4B

14 Bermuda Segment: Opportunities for Growth Remain in Transitioning Market Environment Segment Results Diversified portfolio allows for flexibility 75% 81% 57% 60% 65% 77% 62% 29% 29% 28% 27% 26% 27% 26% 104% 110% 85% 87% 91% 104% 87% 2021 2022 2023 2024 2025 1H 2025 1H 2026 $554 $713 $846 $1,114 $1,406 $841 $908 2021 2022 2023 2024 2025 1H 2025 1H 2026 Bermuda Segment - Gross Premiums Written ($’m) Bermuda Segment - Combined Ratio(2) Loss Ratio Expense Ratio (1) Compound annual growth rate, (2) Numbers may not add due to rounding, (3) Combined ratio excluding the Ukraine Conflict was 101% (3)

Invested Assets

16 Investment Strategy Review – $6.1 Billion Invested Assets Investment Portfolio as of June 30, 2026 PRESERVATION OF CAPITAL LIQUIDITY DIVERSIFICATION ATTRACTIVE RETURNS RISK MANAGEMENT & GOVERNANCE A1 average credit quality 100% investment grade Highly liquid Market sector diversification 4.5% book yield As at 6/30/2026 Investment guidelines from Investment Committee Low correlation to equity markets; long-term positive returns Investments are comprised of exchange traded and other liquid investments 7 unique investment vehicles 13.2% annualized return since inception (2014) Hold lesser of $1.8B or 60% of Hamilton’s net tangible assets in TSHF; arms-length IMA* with Two Sigma Fixed Income, Short-Term and Cash 61% / $3.8B Two Sigma Hamilton Fund 39% / $2.4B *Investment management agreement

17 Fixed Income Investment Portfolio as of June 30, 2026 Invested Assets 56% 20% 7% 17% Corporate US Treasury US Agency Other $3.1B Corporate A3 US Treas. Aa1 US Agency Aa1 Other Aa1 Fixed income investments of $3.1 billion – Average rating of A1 and duration of 4.0 years

18 Two Sigma Hamilton Fund Invested Assets Diversified fund focused on liquid strategies in global equities, fixed income, futures, and FX markets • Two Sigma aims to deliver low-correlated absolute returns primarily through the systematic and non- systematic application of fundamental, technical, alpha capture and event models • Manages over $80B in assets • Deploys and seeks to continuously improve intelligent investment management systems first created in 2001 • Proven, industry leading approach to data science and analytics • Over 1,700 employees of which include an experienced and diverse team of employees in R&D • Seeks to systematically manage risk with human oversight at multiple levels through the investment process • TSHF is a diversified fund focused on liquid strategies in global equities, fixed income, futures and FX markets Two Sigma Hamilton Fund $2.4B TSHF as of June 30, 2026 13.2% Average annualized returns 2014-2Q 2026 Dedicated fund of one Allocation 70% equities 30% macro Highly liquid Investments TSHF Returns Since 2021 1.46 Sharpe Ratio since inception 17.7% 4.6% 7.6% 16.3% 16.0% 9.6% 2021 2022 2023 2024 2025 1H 2026 1) TSHF annual returns correspond to Hamilton’s fiscal year which was Dec 1- Nov 30 until FY 2022.

Investing in Hamilton

20 $17.35 $28.91 $2.00 3Q23 4Q23 1Q24 2Q24 3Q24 4Q24 1Q25 2Q25 3Q25 4Q25 1Q26 2Q26 Book Value Per Share ("BVPS") + Accumulated Dividend Growth Since IPO BVPS Accumulated Dividends A Value Creation Engine: 78% Growth in BVPS + Accumulated Dividends Since IPO Investing in Hamiton

21 Who we are today A scaled, diversified, global specialty insurance and reinsurance operation Entrepreneurial & experienced leadership team fostering a distinctive and attractive culture Disciplined underwriting approach focused on sustainable profitability Demonstrated ability to grow profitably, navigating across market cycles Strong balance sheet with significant financial flexibility Strong financial strength ratings including an A.M. Best “A” rating for Hamilton Re, HIDAC and Hamilton Select Differentiated asset management capabilities due to unique partnership with Two Sigma Poised to deliver significant shareholder value

22 Non-GAAP Measures We present our results of operations in a way that we believe will be the most meaningful and useful to investors, analysts, rating agencies and others who use our financial information to evaluate our performance. Some of the measurements that management uses to assess our operating results are considered non-GAAP financial measures under Regulation G and Item 10(e) of Regulation S-K, each promulgated by the SEC. We believe that these non- GAAP financial measures, which may be defined and calculated differently by other companies, help explain and enhance the understanding of our results of operations. However, these measures should not be viewed as a substitute for those determined in accordance with U.S. GAAP. Where appropriate, reconciliations of our non-GAAP measures to the most directly comparable GAAP financial measures are included below. Underwriting Income (Loss) We calculate underwriting income (loss) on a pre-tax basis as net premiums earned less losses and loss adjustment expenses, acquisition costs and other underwriting expenses (net of third party fee income). We believe that this measure of our performance focuses on the core fundamental performance of the Company’s reportable segments in any given period and is not distorted by investment market conditions, corporate expense allocations or income tax effects. The table below reconciles underwriting income (loss) to net income (loss), the most directly comparable GAAP financial measure:

Hamilton Insurance Group, Ltd. Wellesley House North, 1st Floor 90 Pitts Bay Road, Pembroke HM08, Bermuda +1 (441) 405 5200 hamiltongroup.com Contact us at investor.relations@hamiltongroup.com

Source: View Original Filing on SEC EDGAR

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Hamilton Insurance Group (NYSE: HG) Q2 profit $143.8M with 16.7% premium growth

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