Hamilton Insurance Q3 net income falls to $81.5M

Q: How did HG's investment return break down in Q3 2026?

Hamilton reported total investment return of $88.4 million, including a $144.7 million return from the Two Sigma Hamilton Fund and a $56.3 million loss from fixed income, short-term investments and cash and cash equivalents.

Quarterly premium growth and operating income rose, while common-shareholder net income and underwriting income fell year over year.

Filing Impact

(High)

Filing Sentiment

(Neutral)How Sentiment works

Sentiment and the balance of points

Rhea-AI Sentiment reads the wording of the document, how positive or negative its language is on a 1 to 5 scale. The balance of points shown with the takes weighs what the document actually discloses, so the two can disagree, for example when a trial that missed its main goal is described in upbeat language.

How Sentiment works How the balance works

Form Type

8-K

Rhea-AI Filing Summary

Hamilton Insurance Group, Ltd. (HG) reported third-quarter net income attributable to common shareholders of $81.5 million, versus $136.2 million a year earlier, while operating income attributable to common shareholders was $179.9 million, up from $123.1 million. Gross premiums written rose 17.3% to $819.7 million and net premiums earned rose 13.1% to $591.3 million. Underwriting income was $15.5 million, compared with $64.1 million; the combined ratio was 97.3%, versus 87.8%. A combined ratio below 100% indicates an underwriting profit.

For the nine months ended September 30, 2026, net income attributable to common shareholders was $358.8 million, versus $404.5 million, while operating income was $504.9 million versus $334.3 million. Gross premiums written increased 14.9% to $2.6 billion, and the combined ratio improved to 94.1% from 95.2%. Total investment return was $88.4 million in the quarter, including a $144.7 million Two Sigma Hamilton Fund return and a $56.3 million loss from fixed income, short-term investments and cash and cash equivalents. The company repurchased $3.1 million of common shares during the quarter and paid its previously declared $2.00-per-share special dividend on March 30, 2026.

2 points · 0 major

How this balance works

Rhea-AI gives every point it takes from this document a weight. Minor counts 1, Moderate 3 and Major 9, so one Major point outweighs several Minor ones. The bar adds up the weights on each side, and when neither side holds more than 65% of the total the balance reads Mixed.

It reads the document as published, with the same rules for every company, and it does not look at what the market expected or at how the stock traded, so a point can be objectively good on a day the stock falls.

Rhea-AI Sentiment measures something else, the tone of the wording.

How the balance works How Sentiment works

0 major · 3 points

How the balance works

Positive

Moderate pointGross premiums written increased 17.3% to $819.7 million in Q3 2026.
Moderate pointOperating income attributable to common shareholders rose from $123.1 million to $179.9 million.

Negative

Moderate pointNet income attributable to common shareholders fell from $136.2 million to $81.5 million.
Moderate pointUnderwriting income fell from $64.1 million to $15.5 million.
Moderate pointThe combined ratio rose 9.5 pts, from 87.8% to 97.3%.

Filing Explained

For the first nine months of 2026, Hamilton reports $44.9 million in common-share repurchases; that cumulative figure includes the $3.1 million reported for the third quarter.

8-K Event Classification

2 items: 2.02, 9.01

2 items

Item 2.02 Results of Operations and Financial Condition Financial

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

Item 9.01 Financial Statements and Exhibits Exhibits

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

Key Figures

Net income attributable to common shareholders: $81.5 million Operating income attributable to common shareholders: $179.9 million Gross premiums written: $819.7 million +5 more

8 metrics

Net income attributable to common shareholders $81.5 million Q3 2026; $136.2 million in Q3 2025

Operating income attributable to common shareholders $179.9 million Q3 2026; $123.1 million in Q3 2025

Gross premiums written $819.7 million Q3 2026; increased 17.3% compared with Q3 2025

Net premiums earned $591.3 million Q3 2026; increased 13.1% compared with Q3 2025

Underwriting income $15.5 million Q3 2026; $64.1 million in Q3 2025

Combined ratio 97.3% Q3 2026; 87.8% in Q3 2025

Total investment return $88.4 million Q3 2026

Special dividend $2.00 per share Paid March 30, 2026

Key Terms

Combined Ratio, Attritional Loss Ratio – current year, prior year reserve development, non-GAAP financial measures

4 terms

Combined Ratio financial

"Combined Ratio is a measure of our underwriting profitability"

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 – current year financial

"Attritional Loss Ratio – current year is the attritional losses incurred"

prior year reserve development financial

"Net favorable attritional prior year reserve development"

The change in an insurer’s estimated payouts for claims from earlier reporting years after more information comes in. Like checking a shopping list against the actual receipt, these upward or downward adjustments show whether past estimates were too low or too high and flow through earnings and capital, so investors use them to judge an insurer’s reserving accuracy, future profitability, and balance-sheet risk.

non-GAAP financial measures financial

"considered non-GAAP financial measures under Regulation G"

Non-GAAP financial measures are numbers companies use to show their financial performance that exclude certain expenses or income. They help investors see how the company might perform without one-time costs or other unusual items, giving a different perspective from official reports. However, since they can be adjusted, they don’t always tell the full story and should be looked at alongside standard financial figures.

Earnings Snapshot

Net income attributable to common shareholders: $81.5 million

Three months ended September 30, 2026

Net income attributable to common shareholders $81.5 million Down from $136.2 million in Q3 2025

Operating income attributable to common shareholders $179.9 million Up from $123.1 million in Q3 2025

Gross premiums written $819.7 million Increased 17.3% compared with Q3 2025

Net premiums earned $591.3 million Increased 13.1% compared with Q3 2025

Underwriting income $15.5 million Down from $64.1 million in Q3 2025

Combined ratio 97.3% Up 9.5 pts from 87.8% in Q3 2025

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

How did HG's investment return break down in Q3 2026?

Hamilton reported total investment return of $88.4 million, including a $144.7 million return from the Two Sigma Hamilton Fund and a $56.3 million loss from fixed income, short-term investments and cash and cash equivalents.

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

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Available on EDGAR 10/29/2026 - 04:14 PM EDT Accepted by SEC EDGAR 10/29/2026 - 04:13 PM EDT

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

October 29, 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 October 29, 2026, Hamilton Insurance Group, Ltd. (the “Company”) issued a press release announcing its financial results for the quarter ended September 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 9.01 - Financial Statements and Exhibits

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


Exhibit No.						Description
99.1						Press Release, dated October 29, 2026, issued by Hamilton Insurance Group, Ltd.
99.2						Supplementary Financial Information - September 30, 2026
99.3						Investor Presentation - September 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: October 29, 2026.


			HAMILTON INSURANCE GROUP, LTD.

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

Hamilton Reports 2026 Third Quarter Results

Net Income of $81 million; Annualized Return on Average Equity of 11%

Operating Income of $180 million; Annualized Operating Return on Average Equity of 25%

PEMBROKE, Bermuda, October 29, 2026 – Hamilton Insurance Group, Ltd. (NYSE: HG; “Hamilton” or the “Company”) today announced financial results for the third quarter ended September 30, 2026.

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

“Hamilton delivered exceptional third quarter results, with operating income of $180 million, representing an annualized operating return on average equity of 25%. Gross premiums written increased 17%, reflecting our ability to find attractive opportunities that contribute to the bottom line.

Despite a transitioning market and ongoing geopolitical tensions, Hamilton continues to deliver consistent performance, reflecting the benefits of our diversified platform and our team's ability to navigate the current dynamic market conditions.”

Consolidated Highlights – Third Quarter

•Net income of $81.5 million, or $0.81 per diluted share and operating income of $179.9 million, or $1.78 per diluted share;

•Annualized return on average equity of 11.3% and annualized operating return on average equity of 24.9%;

•Gross premiums written of $819.7 million, an increase of 17.3% compared to the third quarter of 2025;

•Net premiums earned of $591.3 million, an increase of 13.1% compared to the third quarter of 2025;

•Combined ratio of 97.3%;

•Underwriting income of $15.5 million;

•Net investment income of $88.4 million, comprised of Two Sigma Hamilton Fund returns of $144.7 million, and a fixed income, short term and cash and cash equivalents loss of $56.3 million; and

•Repurchased common shares of $3.1 million in the third quarter of 2026.

Consolidated Highlights – Year to Date

•Net income of $358.8 million, or $3.54 per diluted share and operating income of $504.9 million, or $4.98 per diluted share;

•Annualized return on average equity of 16.6% and annualized operating return on average equity of 23.4%;

•Gross premiums written of $2.6 billion, an increase of 14.9% compared to the same period in 2025;

•Net premiums earned of $1.7 billion, an increase of 14.0% compared to the same period in 2025;

•Combined ratio of 94.1%;

•Underwriting income of $102.2 million;

•Net investment income of $323.3 million, comprised of Two Sigma Hamilton Fund returns of $353.2 million, and a fixed income, short term and cash and cash equivalents loss of $29.9 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 $29.80, an increase of 4.6% compared to December 31, 2025;

•Book value per common share plus accumulated dividends of $31.80, an increase of 11.6% compared to December 31, 2025; and

•Repurchased common shares of $44.9 million in 2026.

Consolidated Results – Third Quarter


	For the Three Months Ended
($ in thousands, except for per share amounts and percentages)	September 30, 2026		September 30, 2025		Change
Gross premiums written	$	819,702	$	698,845	$	120,857
Net premiums written	626,722		578,981		47,741
Net premiums earned	591,274		522,999		68,275
Underwriting income (loss)	$	15,527	$	64,089	$	(48,562)
Combined ratio	97.3%		87.8%		9.5 pts

Net income (loss) attributable to common shareholders	$	81,456	$	136,200	$	(54,744)
Income (loss) per share attributable to common shareholders - diluted	$	0.81	$	1.32


Book value per common share	$	29.80	$	27.06

Accumulated dividends	$	2.00	$	—
Book value per common share plus accumulated dividends	$	31.80	$	27.06


Return on average common equity - annualized	11.3%		20.9%


	For the Three Months Ended
Key Ratios	September 30, 2026		September 30, 2025		Change
Attritional loss ratio - current year	57.5	%	55.4	%	2.1	pts
Attritional loss ratio - prior year	(4.6	%)	(2.1	%)	(2.5	pts)
Catastrophe loss ratio - current year	1.1	%	0.0	%	1.1	pts
Catastrophe loss ratio - prior year	8.0	%	0.0	%	8.0	pts
Loss and loss adjustment expense ratio	62.0	%	53.3	%	8.7	pts
Acquisition cost ratio	25.5	%	24.0	%	1.5	pts
Other underwriting expense ratio	9.8	%	10.5	%	(0.7	pts)
Combined ratio	97.3	%	87.8	%	9.5	pts

•Gross premiums written increased by $120.9 million, or 17.3%, to $819.7 million, with an increase of $76.4 million, or 20.1%, in the International Segment, and $44.5 million, or 13.9%, in the Bermuda Segment.

•Net premiums written increased by $47.7 million, or 8.2%, to $626.7 million, with an increase of $44.8 million, or 14.7%, in the International Segment, and $2.9 million, or 1.1%, in the Bermuda Segment.

•Net premiums earned increased by $68.3 million, or 13.1%, to $591.3 million, with an increase of $57.0 million, or 22.6%, in the International Segment, and $11.3 million, or 4.2%, in the Bermuda Segment.

•The attritional loss ratio (current year), net of reinsurance, was 57.5%. The increase of 2.1 points was primarily driven by a change in business mix, including more casualty reinsurance business and the impact of one large loss in our specialty and property reinsurance classes.

•Net favorable attritional prior year reserve development, net of reinsurance, was $27.2 million, primarily driven by favorable development in certain specialty classes.

•Catastrophe losses (current and prior year), net of reinsurance, were $53.9 million, driven by the Middle East conflict ($6.8 million), in addition to unfavorable prior year development relating to the Ukraine conflict ($47.1 million).

•The acquisition cost ratio increased by 1.5 points compared to the same period in 2025, primarily driven by a change in business mix.

•The other underwriting expense ratio decreased by 0.7 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 – Third Quarter


International Segment	For the Three Months Ended
($ in thousands, except for percentages)	September 30, 2026			September 30, 2025			Change
Gross premiums written	$	456,332		$	379,957		$	76,375
Net premiums written	349,250			304,410			44,840
Net premiums earned	309,313			252,302			57,011
Underwriting income (loss)	$	8,959		$	11,834		$	(2,875)

Key Ratios
Attritional loss ratio - current year	54.5		%	55.3		%	(0.8		pts)
Attritional loss ratio - prior year	(3.2		%)	(2.2		%)	(1.0		pts)
Catastrophe loss ratio - current year	2.2		%	0.0		%	2.2		pts
Catastrophe loss ratio - prior year	1.4		%	0.0		%	1.4		pts
Loss and loss adjustment expense ratio	54.9		%	53.1		%	1.8		pts
Acquisition cost ratio	27.8		%	26.6		%	1.2		pts
Other underwriting expense ratio	14.4		%	15.7		%	(1.3		pts)
Combined ratio	97.1		%	95.4		%	1.7		pts

•Gross premiums written increased by $76.4 million, or 20.1%, to $456.3 million, primarily driven by growth in both new and existing business in specialty and casualty insurance classes and specialty reinsurance classes.

•The attritional loss ratio (current year), net of reinsurance, was 54.5%, a decrease of 0.8 points.

•Net favorable attritional prior year reserve development, net of reinsurance, was $9.9 million, primarily driven by favorable development in certain specialty classes.

•Catastrophe losses (current and prior year), net of reinsurance, were $11.3 million, driven by the Middle East conflict ($6.8 million), in addition to unfavorable prior year development relating to the Ukraine conflict ($4.5 million).

•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 1.3 points compared to the same period in 2025, primarily driven by growth in the premium base.

Bermuda Segment Underwriting Results – Third Quarter


Bermuda Segment	For the Three Months Ended
($ in thousands, except for percentages)	September 30, 2026			September 30, 2025			Change
Gross premiums written	$	363,370		$	318,888		$	44,482
Net premiums written	277,472			274,571			2,901
Net premiums earned	281,961			270,697			11,264
Underwriting income (loss)	$	6,568		$	52,255		$	(45,687)

Key Ratios
Attritional loss ratio - current year	60.8		%	55.6		%	5.2		pts
Attritional loss ratio - prior year	(6.1		%)	(2.1		%)	(4.0		pts)
Catastrophe loss ratio - current year	0.0		%	0.0		%	0.0		pts
Catastrophe loss ratio - prior year	15.1		%	0.0		%	15.1		pts
Loss and loss adjustment expense ratio	69.8		%	53.5		%	16.3		pts
Acquisition cost ratio	23.1		%	21.6		%	1.5		pts
Other underwriting expense ratio	4.8		%	5.6		%	(0.8		pts)
Combined ratio	97.7		%	80.7		%	17.0		pts

•Gross premiums written increased by $44.5 million, or 13.9%, to $363.4 million, primarily driven by growth in both new and existing business in casualty and specialty reinsurance classes.

•The attritional loss ratio (current year), net of reinsurance, was 60.8%. The increase of 5.2 points was primarily driven by one large loss in our specialty and property reinsurance classes and a change in business mix, including an increase in casualty reinsurance business.

•Net favorable attritional prior year reserve development, net of reinsurance, was $17.3 million, primarily driven by favorable development in certain specialty classes.

•Catastrophe losses (current and prior year), net of reinsurance, were $42.6 million, driven by unfavorable prior year development relating to the Ukraine conflict ($42.6 million).

•The acquisition cost ratio increased by 1.5 points compared to the same period in 2025, primarily driven by a change in business mix.

•The other underwriting expense ratio decreased by 0.8 points compared to the same period in 2025, driven by the Bermuda substance-based tax credits and an increase in net premiums earned.

Consolidated Results – Year to Date


	For the Nine Months Ended
($ in thousands, except for per share amounts and percentages)	September 30, 2026		September 30, 2025		Change
Gross premiums written	$	2,590,854	$	2,254,177	$	336,677
Net premiums written	1,902,077		1,739,169		162,908
Net premiums earned	1,747,797		1,533,090		214,707
Underwriting income (loss)	$	102,221	$	73,288	$	28,933
Combined ratio	94.1%		95.2%		(1.1 pts)

Net income (loss) attributable to common shareholders	$	358,776	$	404,486	$	(45,710)
Income (loss) per share attributable to common shareholders - diluted	$	3.54	$	3.88
Book value per common share	$	29.80	$	27.06

Accumulated dividends	$	2.00	$	—
Book value per common share plus accumulated dividends	$	31.80	$	27.06
Change in book value per common share plus accumulated dividends	11.6%		17.9%

Return on average common equity - annualized	16.6%		21.6%


	For the Nine Months Ended
Key Ratios	September 30, 2026		September 30, 2025		Change
Attritional loss ratio - current year	55.1	%	53.4	%	1.7	pts
Attritional loss ratio - prior year	(0.8	%)	(1.8	%)	1.0	pts
Catastrophe loss ratio - current year	3.0	%	11.1	%	(8.1	pts)
Catastrophe loss ratio - prior year	2.9	%	(1.1	%)	4.0	pts
Loss and loss adjustment expense ratio	60.2	%	61.6	%	(1.4	pts)
Acquisition cost ratio	25.2	%	23.8	%	1.4	pts
Other underwriting expense ratio	8.7	%	9.8	%	(1.1	pts)
Combined ratio	94.1	%	95.2	%	(1.1	pts)

•Gross premiums written increased by $336.7 million, or 14.9%, to $2.6 billion, with an increase of $224.6 million, or 20.5%, in the International Segment, and $112.1 million, or 9.7%, in the Bermuda Segment.

•Net premiums written increased by $162.9 million, or 9.4%, to $1.9 billion, with an increase of $168.1 million, or 21.2%, in the International Segment, and a decrease of $5.1 million, or 0.5%, in the Bermuda Segment.

•Net premiums earned increased by $214.7 million, or 14.0%, to $1.7 billion, with an increase of $156.7 million, or 21.0%, in the International Segment, and $58.1 million, or 7.4%, in the Bermuda Segment.

•The attritional loss ratio (current year), net of reinsurance, was 55.1%. The increase of 1.7 points was primarily driven by a change in business mix, including more casualty reinsurance and specialty insurance business and the impact of one large loss in our specialty and property reinsurance classes.

•Net favorable attritional prior year reserve development, net of reinsurance, was $14.1 million, primarily driven by favorable development in certain specialty and property classes, partially offset by additional loss information in relation to the Baltimore Bridge collapse, and unfavorable development in certain casualty classes.

•Catastrophe losses (current and prior year), net of reinsurance, were $103.8 million, driven by the Middle East conflict ($52.6 million), in addition to unfavorable prior year development relating to the Ukraine conflict ($47.1 million) and other unfavorable prior year development ($4.1 million).

•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 1.1 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 Nine Months Ended
($ in thousands, except for percentages)	September 30, 2026			September 30, 2025			Change
Gross premiums written	$	1,319,314		$	1,094,715		$	224,599
Net premiums written	959,530			791,473			168,057
Net premiums earned	902,728			746,078			156,650
Underwriting income (loss)	$	25,064		$	39,766		$	(14,702)

Key Ratios
Attritional loss ratio - current year	53.5		%	53.1		%	0.4		pts
Attritional loss ratio - prior year	(2.2		%)	(2.9		%)	0.7		pts
Catastrophe loss ratio - current year	4.5		%	4.1		%	0.4		pts
Catastrophe loss ratio - prior year	0.5		%	(0.1		%)	0.6		pts
Loss and loss adjustment expense ratio	56.3		%	54.2		%	2.1		pts
Acquisition cost ratio	27.4		%	26.2		%	1.2		pts
Other underwriting expense ratio	13.5		%	14.3		%	(0.8		pts)
Combined ratio	97.2		%	94.7		%	2.5		pts

•Gross premiums written increased by $224.6 million, or 20.5%, to $1.3 billion, primarily driven by growth in both new and existing business in specialty and casualty insurance classes.

•The attritional loss ratio (current year), net of reinsurance, was 53.5%, an increase of 0.4 points compared to the same period in 2025.

•Net favorable attritional prior year reserve development, net of reinsurance, was $19.8 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 $45.0 million, driven by the Middle East conflict ($40.5 million), in addition to unfavorable prior year development relating to the Ukraine conflict ($4.5 million).

•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 0.8 points compared to the same period in 2025, primarily driven by growth in the premium base.

Bermuda Segment Underwriting Results – Year to Date


Bermuda Segment	For the Nine Months Ended
($ in thousands, except for percentages)	September 30, 2026			September 30, 2025			Change
Gross premiums written	$	1,271,540		$	1,159,462		$	112,078
Net premiums written	942,547			947,696			(5,149)
Net premiums earned	845,069			787,012			58,057
Underwriting income (loss)	$	77,157		$	33,522		$	43,635

Key Ratios
Attritional loss ratio - current year	56.9		%	53.9		%	3.0		pts
Attritional loss ratio - prior year	0.7		%	(0.8		%)	1.5		pts
Catastrophe loss ratio - current year	1.4		%	17.7		%	(16.3		pts)
Catastrophe loss ratio - prior year	5.5		%	(2.2		%)	7.7		pts
Loss and loss adjustment expense ratio	64.5		%	68.6		%	(4.1		pts)
Acquisition cost ratio	22.9		%	21.6		%	1.3		pts
Other underwriting expense ratio	3.5		%	5.6		%	(2.1		pts)
Combined ratio	90.9		%	95.8		%	(4.9		pts)

•Gross premiums written increased by $112.1 million, or 9.7%, to $1.3 billion, 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 as a result of lower reinstatement premiums and rate decreases.

•The attritional loss ratio (current year), net of reinsurance, was 56.9%. The increase of 3.0 points was primarily driven by a change in business mix, including an increase in casualty reinsurance business and the impact of one large loss in our specialty and property reinsurance classes.

•Net unfavorable attritional prior year reserve development, net of reinsurance, was $5.7 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.

•Catastrophe losses (current and prior year), net of reinsurance, were $58.8 million, driven by the Middle East conflict ($12.1 million), in addition to unfavorable prior year development relating to the Ukraine conflict ($42.6 million), and other unfavorable prior year development ($4.1 million).

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

Investments and Shareholders’ Equity as of September 30, 2026

•Total cash and invested assets of $6.4 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 $29.80 compared to $28.50 at December 31, 2025, an increase of 4.6%.

•Book value per share plus accumulated dividends, of $31.80 compared to $28.50 at December 31, 2025, an increase of 11.6%.

Conference Call Details and Additional Information

Conference Call Information

Hamilton will host a conference call to discuss its financial results on Friday, October 30, 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)	September 30, 2026		December 31, 2025
Assets
Fixed maturity investments, at fair value (amortized cost 2026: $3,267,687; 2025: $3,210,940)	$	3,157,925	$	3,238,543
Short-term investments, at fair value (amortized cost 2026: $423,363; 2025: $200,052)	424,046		200,459
Investments in Two Sigma Funds, at fair value (cost 2026: $1,471,985; 2025: $1,355,563)	1,873,879		1,587,658
Total investments	5,455,850		5,026,660
Cash and cash equivalents	1,184,318		1,062,359
Restricted cash and cash equivalents	129,300		109,731
Premiums receivable	1,209,434		939,777
Paid losses recoverable	198,835		93,659
Deferred acquisition costs	297,055		257,203
Unpaid losses and loss adjustment expenses recoverable	1,468,584		1,375,857
Receivables for investments sold	45,425		58,029
Prepaid reinsurance	452,409		296,351
Intangible assets	81,821		86,624
Other assets	303,990		265,363
Total assets	$	10,827,021	$	9,571,613

Liabilities, non-controlling interest, and shareholders’ equity
Liabilities
Reserve for losses and loss adjustment expenses	$	4,988,921	$	4,415,176
Unearned premiums	1,687,812		1,377,474
Reinsurance balances payable	507,737		296,400
Payables for investments purchased	162,951		209,853
Term loan, net of issuance costs	149,821		149,743
Accounts payable and accrued expenses	173,565		177,320
Payables to related parties	87,419		123,376
Total liabilities	7,758,226		6,749,342

Non-controlling interest – TS Hamilton Fund	132,921		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: 85,157,932 and 2025: 84,677,932 ), par value $0.01; issued and outstanding (2026: 66,278,404 and 2025: 66,305,707)	663		663
Class C, authorized (2026: 14,923,649 and 2025: 15,403,649), par value $0.01; issued and outstanding (2026: 14,923,649 and 2025: 15,403,649)	149		154
Additional paid-in capital	1,132,118		1,134,985
Accumulated other comprehensive loss	(4,441)		(4,441)
Retained earnings	1,807,212		1,690,565
Total shareholders’ equity	2,935,874		2,822,099

Total liabilities, non-controlling interest, and shareholders’ equity	$	10,827,021	$	9,571,613

Consolidated Statement of Operations


	Three Months Ended				Nine Months Ended
	September 30,				September 30,
($ in thousands, except for per share amounts)	2026		2025		2026		2025
Revenues
Gross premiums written	$	819,702	$	698,845	$	2,590,854	$	2,254,177
Reinsurance premiums ceded	(192,980)		(119,864)		(688,777)		(515,008)
Net premiums written	626,722		578,981		1,902,077		1,739,169

Net change in unearned premiums	(35,448)		(55,982)		(154,280)		(206,079)
Net premiums earned	591,274		522,999		1,747,797		1,533,090

Net realized and unrealized gains (losses) on investments	208,526		115,136		587,458		571,964
Net investment income (loss)	26,615		22,727		77,084		62,721
Total net realized and unrealized gains (losses) on investments and net investment income (loss)	235,141		137,863		664,542		634,685


Other income (loss)	2,812		4,169		13,466		13,845
Net foreign exchange gains (losses)	(1,188)		2,619		719		(4,422)
Total revenues	828,039		667,650		2,426,524		2,177,198

Expenses
Losses and loss adjustment expenses	366,726		278,712		1,053,000		943,875
Acquisition costs	150,972		125,412		440,902		365,108
General and administrative expenses	74,958		74,302		203,353		205,832

Amortization of intangible assets	3,762		4,000		11,482		11,895
Interest expense	4,801		4,933		14,339		15,264
Total expenses	601,219		487,359		1,723,076		1,541,974

Income (loss) before income tax	226,820		180,291		703,448		635,224
Income tax expense (benefit)	(1,363)		3,866		3,430		9,748
Net income (loss)	228,183		176,425		700,018		625,476

Net income (loss) attributable to non-controlling interest	146,727		40,225		341,242		220,990

Net income (loss) and other comprehensive income (loss) attributable to common shareholders	$	81,456	$	136,200	$	358,776	$	404,486

Per share data
Basic income (loss) per share attributable to common shareholders	$	0.82	$	1.37	$	3.62	$	4.01
Diluted income (loss) per share attributable to common shareholders	$	0.81	$	1.32	$	3.54	$	3.88

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				Nine Months Ended
	September 30,				September 30,
($ in thousands, except for per share amounts)	2026		2025		2026		2025
Net income (loss) and other comprehensive income (loss) attributable to common shareholders	$	81,456	$	136,200	$	358,776	$	404,486
Adjustment for:
Net realized (gains) losses on investments - Fixed maturity and short-term investments(1)	6,983		(3,274)		9,316		(4,140)
Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1)	90,312		(7,227)		137,483		(70,496)
Net foreign exchange (gains) losses	1,188		(2,619)		(719)		4,422
Operating income (loss) attributable to common shareholders	$	179,939	$	123,080	$	504,856	$	334,272


Net income (loss) and other comprehensive income (loss) attributable to common shareholders per common share - diluted	$	0.81	$	1.32	$	3.54	$	3.88
Adjustment for:
Net realized (gains) losses on investments - Fixed maturity and short-term investments(1)	0.07		(0.03)		0.09		(0.04)
Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1)	0.89		(0.07)		1.36		(0.68)
Net foreign exchange (gains) losses	0.01		(0.02)		(0.01)		0.04
Operating income (loss) attributable to common shareholders per common share - diluted	$	1.78	$	1.20	$	4.98	$	3.20


Return on average common shareholders’ equity - annualized	11.3	%	20.9	%	16.6	%	21.6	%
Adjustment for:
Net realized (gains) losses on investments - Fixed maturity and short-term investments(1)	1.0	%	(0.5)	%	0.4	%	(0.2)	%
Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1)	12.5	%	(1.1)	%	6.4	%	(3.7)	%
Net foreign exchange (gains) losses	0.1	%	(0.4)	%	—	%	0.2	%
Operating return on average common shareholders’ equity - annualized	24.9	%	18.9	%	23.4	%	17.9	%

(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				Nine Months Ended
	September 30,				September 30,
($ in thousands)	2026		2025		2026		2025
Underwriting income (loss)	$	15,527	$	64,089	$	102,221	$	73,288
Total net realized and unrealized gains (losses) on investments and net investment income (loss)	235,141		137,863		664,542		634,685


Net foreign exchange gains (losses)	(1,188)		2,619		719		(4,422)
Corporate expenses	(14,097)		(15,347)		(38,213)		(41,168)

Amortization of intangible assets	(3,762)		(4,000)		(11,482)		(11,895)
Interest expense	(4,801)		(4,933)		(14,339)		(15,264)
Income tax (expense) benefit	1,363		(3,866)		(3,430)		(9,748)
Net income (loss), prior to non-controlling interest	$	228,183	$	176,425	$	700,018	$	625,476

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).

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


	Three Months Ended				Nine Months Ended
	September 30,				September 30,
($ in thousands)	2026		2025		2026		2025
Third party fee income	$	2,812	$	4,169	$	13,466	$	13,845

Other income (loss)	$	2,812	$	4,169	$	13,466	$	13,845

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				Nine Months Ended
	September 30,				September 30,
($ in thousands)	2026		2025		2026		2025
Other underwriting expenses	$	60,861	$	58,955	$	165,140	$	164,664
Corporate expenses	14,097		15,347		38,213		41,168
General and administrative expenses	$	74,958	$	74,302	$	203,353	$	205,832

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 September 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 September 30, Nine Months Ended September 30, Year Ended ($ in thousands) 2026 2025 2026 2025 2025 Net income (loss) attributable to common shareholders ........................................................ $ 81,456 $ 136,200 $ 358,776 $ 404,486 $ 576,670 Operating income (loss) attributable to common shareholders ............................................ $ 179,939 $ 123,080 $ 504,856 $ 334,272 $ 502,515 Underwriting income (loss) Gross premiums written ............................................................................................................... $ 819,702 $ 698,845 $ 2,590,854 $ 2,254,177 $ 2,923,145 Net premiums written ................................................................................................................... 626,722 578,981 1,902,077 1,739,169 2,287,543 Net premiums earned .................................................................................................................. 591,274 522,999 1,747,797 1,533,090 2,109,776 Underwriting income (loss) .......................................................................................................... $ 15,527 $ 64,089 $ 102,221 $ 73,288 $ 148,823 Key Ratios: Attritional loss ratio - current year .............................................................................................. 57.5 % 55.4 % 55.1 % 53.4 % 54.4 % Attritional loss ratio - prior year development ........................................................................... (4.6) % (2.1) % (0.8) % (1.8) % (2.2) % Catastrophe loss ratio - current year ......................................................................................... 1.1 % 0.0 % 3.0 % 11.1 % 8.4 % Catastrophe loss ratio - prior year development ...................................................................... 8.0 % 0.0 % 2.9 % (1.1) % (0.9) % Loss and loss adjustment expense ratio ................................................................................... 62.0 % 53.3 % 60.2 % 61.6 % 59.7 % Acquisition cost ratio .................................................................................................................... 25.5 % 24.0 % 25.2 % 23.8 % 24.0 % Other underwriting expense ratio ............................................................................................... 9.8 % 10.5 % 8.7 % 9.8 % 9.2 % Combined ratio .............................................................................................................................. 97.3 % 87.8 % 94.1 % 95.2 % 92.9 % Investments Total assets .................................................................................................................................... $ 10,827,021 $ 9,213,370 $ 10,827,021 $ 9,213,370 $ 9,571,613 Total cash and invested assets(1) ............................................................................................... 6,431,602 5,670,829 6,431,602 5,670,829 5,923,378 Total investment return(2) ............................................................................................................. 88,414 97,638 323,300 413,695 511,773 Two Sigma Hamilton Fund Total net realized and unrealized gains (losses) on investments and net investment income (loss) - TSHF ................................................................................................................... 291,416 94,469 694,465 465,888 564,254 Net income (loss) attributable to non-controlling interest - TSHF ......................................... 146,727 40,225 341,242 220,990 263,359 $ 144,689 $ 54,244 $ 353,223 $ 244,898 $ 300,895 Two Sigma Hamilton Fund return, net of investment management fees and performance incentive allocations .............................................................................................. 6.1 % 2.6 % 16.3 % 13.0 % 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 .................................................................................................................... $ (56,275) $ 43,394 $ (29,923) $ 168,797 $ 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 September 30, Nine Months Ended September 30, Year Ended ($ in thousands, except per share amounts) 2026 2025 2026 2025 2025 Income (loss) per share attributable to common shareholders - basic ................................ $ 0.82 $ 1.37 $ 3.62 $ 4.01 $ 5.75 Income (loss) per share attributable to common shareholders - diluted .............................. $ 0.81 $ 1.32 $ 3.54 $ 3.88 $ 5.55 Operating income (loss) attributable to common shareholders per common share - diluted ............................................................................................................................................. $ 1.78 $ 1.20 $ 4.98 $ 3.20 $ 4.84 Weighted average common shares outstanding - basic ........................................................ 98,825,926 99,235,535 99,221,564 100,855,910 100,363,570 Weighted average common shares outstanding - diluted ...................................................... 100,908,417 102,904,248 101,296,020 104,307,599 103,844,198 Return on average common shareholders' equity - annualized ............................................ 11.3 % 20.9 % 16.6 % 21.6 % 22.4 % Operating return on average common shareholders' equity - annualized ........................... 24.9 % 18.9 % 23.4 % 17.9 % 19.5 % September 30, 2026 December 31, 2025 Closing common shareholders' equity, less intangible assets .............................................. $ 2,854,053 $ 2,735,475 Closing common shareholders' equity ...................................................................................... $ 2,935,874 $ 2,822,099 Closing common shares outstanding ........................................................................................ 98,522,131 99,029,434 Book Value per Common Share Book value per common share ................................................................................................ $ 29.80 $ 28.50 Accumulated dividends ............................................................................................................. $ 2.00 $ — Book value per common share plus accumulated dividends .............................................. $ 31.80 $ 28.50 Year to date change in book value per common share plus accumulated dividends ..... 11.6 % 24.2 % Tangible Book Value per Common Share Tangible book value per common share ................................................................................ $ 28.97 $ 27.62 Accumulated dividends ............................................................................................................. $ 2.00 $ — Tangible book value per common share plus accumulated dividends .............................. $ 30.97 $ 27.62 Year to date change in tangible book value per common share plus accumulated dividends ..................................................................................................................................... 12.1 % 25.4 % Financial Highlights Key Operating and Financial Metrics

6 Three Months Ended September 30, Nine Months Ended September 30, Year Ended ($ in thousands, except per share amounts) 2026 2025 2026 2025 2025 Revenues Gross premiums written ............................................................................................................... $ 819,702 $ 698,845 $ 2,590,854 $ 2,254,177 $ 2,923,145 Reinsurance premiums ceded .................................................................................................... (192,980) (119,864) (688,777) (515,008) (635,602) Net premiums written ................................................................................................................... 626,722 578,981 1,902,077 1,739,169 2,287,543 Net change in unearned premiums ............................................................................................ (35,448) (55,982) (154,280) (206,079) (177,767) Net premiums earned .................................................................................................................. 591,274 522,999 1,747,797 1,533,090 2,109,776 Net realized and unrealized gains (losses) on investments .................................................. 208,526 115,136 587,458 571,964 687,111 Net investment income (loss) ..................................................................................................... 26,615 22,727 77,084 62,721 88,021 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ................................................................................................................................. 235,141 137,863 664,542 634,685 775,132 Third party fee income ................................................................................................................. 2,812 4,169 13,466 13,845 26,601 Net foreign exchange gains (losses) ......................................................................................... (1,188) 2,619 719 (4,422) (5,985) Total revenues ............................................................................................................................. 828,039 667,650 2,426,524 2,177,198 2,905,524 Expenses Losses and loss adjustment expenses ..................................................................................... 366,726 278,712 1,053,000 943,875 1,258,521 Acquisition costs ........................................................................................................................... 150,972 125,412 440,902 365,108 507,290 Other underwriting expenses ...................................................................................................... 60,861 58,955 165,140 164,664 221,743 Corporate expenses ..................................................................................................................... 14,097 15,347 38,213 41,168 57,167 Amortization of intangible assets ............................................................................................... 3,762 4,000 11,482 11,895 15,709 Interest expense ........................................................................................................................... 4,801 4,933 14,339 15,264 20,189 Total expenses ............................................................................................................................ 601,219 487,359 1,723,076 1,541,974 2,080,619 Income (loss) before income tax ................................................................................................ 226,820 180,291 703,448 635,224 824,905 Income tax expense (benefit) ..................................................................................................... (1,363) 3,866 3,430 9,748 (15,124) Net income (loss) ........................................................................................................................ 228,183 176,425 700,018 625,476 840,029 Net income (loss) attributable to non-controlling interest ....................................................... 146,727 40,225 341,242 220,990 263,359 Net income (loss) and other comprehensive income (loss) attributable to common shareholders .............................................................................................................. $ 81,456 $ 136,200 $ 358,776 $ 404,486 $ 576,670 Per share data Income (loss) per share attributable to common shareholders - basic ................................ $ 0.82 $ 1.37 $ 3.62 $ 4.01 $ 5.75 Income (loss) per share attributable to common shareholders - diluted .............................. $ 0.81 $ 1.32 $ 3.54 $ 3.88 $ 5.55 Return on average common shareholders' equity - annualized ............................................ 11.3 % 20.9 % 16.6 % 21.6 % 22.4 % Summary Consolidated Results Statements of Operations

7 September 30, June 30, March 31, December 31, September 30, ($ in thousands, except share information) 2026 2026 2026 2025 2025 Assets Fixed maturity investments, at fair value (amortized cost September 30, 2026: $3,267,687) ...................................... $ 3,157,925 $ 3,114,054 $ 3,016,314 $ 3,238,543 $ 3,022,441 Short-term investments, at fair value (amortized cost September 30, 2026: $423,363) ............................................... 424,046 356,453 451,185 200,459 248,847 Investments in Two Sigma Funds, at fair value (cost September 30, 2026: $1,471,985) ............................................. 1,873,879 1,844,158 1,685,031 1,587,658 1,500,672 Total investments ....................................................................................................................................................................... 5,455,850 5,314,665 5,152,530 5,026,660 4,771,960 Cash and cash equivalents ...................................................................................................................................................... 1,184,318 717,335 842,484 1,062,359 955,130 Restricted cash and cash equivalents ................................................................................................................................... 129,300 111,631 113,033 109,731 110,087 Premiums receivable ................................................................................................................................................................ 1,209,434 1,240,034 1,154,469 939,777 1,012,000 Paid losses recoverable ........................................................................................................................................................... 198,835 99,228 100,187 93,659 115,847 Deferred acquisition costs ........................................................................................................................................................ 297,055 294,669 291,312 257,203 259,260 Unpaid losses and loss adjustment expenses recoverable ................................................................................................ 1,468,584 1,463,936 1,412,974 1,375,857 1,303,833 Receivables for investments sold ........................................................................................................................................... 45,425 185,133 10,046 58,029 45,182 Prepaid reinsurance .................................................................................................................................................................. 452,409 454,535 418,978 296,351 334,025 Intangible assets ........................................................................................................................................................................ 81,821 83,163 84,331 86,624 88,848 Other assets ............................................................................................................................................................................... 303,990 299,570 283,665 265,363 217,198 Total assets .............................................................................................................................................................................. $ 10,827,021 $ 10,263,899 $ 9,864,009 $ 9,571,613 $ 9,213,370 Liabilities, non-controlling interest, and shareholders' equity Liabilities Reserve for losses and loss adjustment expenses .............................................................................................................. $ 4,988,921 $ 4,783,094 $ 4,595,810 $ 4,415,176 $ 4,206,077 Unearned premiums ................................................................................................................................................................. 1,687,812 1,654,491 1,583,245 1,377,474 1,443,460 Reinsurance balances payable ............................................................................................................................................... 507,737 491,148 460,804 296,400 372,711 Payables for investments purchased ..................................................................................................................................... 162,951 61,071 110,151 209,853 102,013 Term loan, net of issuance costs ............................................................................................................................................ 149,821 149,795 149,769 149,743 149,717 Accounts payable and accrued expenses ............................................................................................................................. 173,565 131,905 149,185 177,320 167,882 Payables to related parties ...................................................................................................................................................... 87,419 67,946 62,058 123,376 28,338 Total liabilities .......................................................................................................................................................................... 7,758,226 7,339,450 7,111,022 6,749,342 6,470,198 Non-controlling interest - TS Hamilton Fund ................................................................................................................... 132,921 73,613 30,537 172 81,179 Shareholders' equity Common shares: Class A, authorized (September 30, 2026: 26,444,807), par value $0.01; issued and outstanding (September 30, 2026: 17,320,078) .............................................................................................................................................................. 173 173 173 173 178 Class B, authorized (September 30, 2026: 85,157,932), par value $0.01; issued and outstanding (September 30, 2026: 66,278,404) .............................................................................................................................................................. 663 659 665 663 645 Class C, authorized (September 30, 2026: 14,923,649), par value $0.01; issued and outstanding (September 30, 2026: 14,923,649) .............................................................................................................................................................. 149 154 154 154 160 Additional paid-in-capital .......................................................................................................................................................... 1,132,118 1,126,425 1,127,868 1,134,985 1,135,815 Accumulated other comprehensive loss ................................................................................................................................ (4,441) (4,441) (4,441) (4,441) (4,441) Retained earnings ..................................................................................................................................................................... 1,807,212 1,727,866 1,598,031 1,690,565 1,529,636 Total shareholders' equity .................................................................................................................................................... 2,935,874 2,850,836 2,722,450 2,822,099 2,661,993 Total liabilities, non-controlling interest, and shareholders' equity ......................................................................... $ 10,827,021 $ 10,263,899 $ 9,864,009 $ 9,571,613 $ 9,213,370 Summary Consolidated Results Consolidated Balance Sheets

8 September 30, 2026 ($ in thousands) Consolidated GAAP Balance Sheet Two Sigma Hamilton Fund Balances Unconsolidated Balance Sheet(1) Assets Fixed maturity investments, at fair value .................................................................................................................................................................................... $ 3,157,925 $ - $ 3,157,925 Short-term investments, at fair value ......................................................................................................................................................................................... 424,046 (423,492) 554 Investments in Two Sigma Funds, at fair value ........................................................................................................................................................................ 1,873,879 648,556 2,522,435 Total investments ............................................................................................................................................................................................................................ 5,455,850 225,064 5,680,914 Cash and cash equivalents .......................................................................................................................................................................................................... 1,184,318 (528,992) 655,326 Restricted cash and cash equivalents ........................................................................................................................................................................................ 129,300 - 129,300 Premiums receivable ..................................................................................................................................................................................................................... 1,209,434 - 1,209,434 Paid losses recoverable ................................................................................................................................................................................................................ 198,835 - 198,835 Deferred acquisition costs ............................................................................................................................................................................................................ 297,055 - 297,055 Unpaid losses and loss adjustment expenses recoverable .................................................................................................................................................... 1,468,584 - 1,468,584 Receivables for investments sold ................................................................................................................................................................................................ 45,425 (45,303) 122 Prepaid reinsurance ....................................................................................................................................................................................................................... 452,409 - 452,409 Intangible assets ............................................................................................................................................................................................................................ 81,821 - 81,821 Other assets .................................................................................................................................................................................................................................... 303,990 (534) 303,456 Total assets ................................................................................................................................................................................................................................... $ 10,827,021 $ (349,765) $ 10,477,256 Liabilities, non-controlling interest, and shareholders' equity Liabilities Reserve for losses and loss adjustment expenses .................................................................................................................................................................. $ 4,988,921 $ - $ 4,988,921 Unearned premiums ...................................................................................................................................................................................................................... 1,687,812 - 1,687,812 Reinsurance balances payable .................................................................................................................................................................................................... 507,737 - 507,737 Payables for investments purchased .......................................................................................................................................................................................... 162,951 (129,225) 33,726 Term loan, net of issuance costs ................................................................................................................................................................................................. 149,821 - 149,821 Accounts payable and accrued expenses .................................................................................................................................................................................. 173,565 (200) 173,365 Payables to related parties ........................................................................................................................................................................................................... 87,419 (87,419) - Total liabilities ............................................................................................................................................................................................................................... 7,758,226 (216,844) 7,541,382 Non-controlling interest - TS Hamilton Fund ....................................................................................................................................................................... 132,921 (132,921) - Shareholders' equity Common shares: Class A, par value $0.01 ............................................................................................................................................................................................................... 173 - 173 Class B, par value $0.01 ............................................................................................................................................................................................................... 663 - 663 Class C, par value $0.01 ............................................................................................................................................................................................................... 149 - 149 Additional paid-in-capital ............................................................................................................................................................................................................... 1,132,118 - 1,132,118 Accumulated other comprehensive loss ..................................................................................................................................................................................... (4,441) - (4,441) Retained earnings .......................................................................................................................................................................................................................... 1,807,212 - 1,807,212 Total shareholders' equity ......................................................................................................................................................................................................... 2,935,874 - 2,935,874 Total liabilities, non-controlling interest, and shareholders' equity .............................................................................................................................. $ 10,827,021 $ (349,765) $ 10,477,256 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 September 30, Nine Months Ended September 30, Year Ended ($ in thousands) 2026 2025 2026 2025 2025 Net realized gains (losses) on investments ........................................................................ $ 166,722 $ 109,355 $ 554,472 $ 424,142 $ 517,147 Fixed maturities and short-term investments ........................................................................ (6,983) 3,274 (9,316) 4,140 7,369 TS Hamilton Fund ...................................................................................................................... 173,705 106,081 563,788 420,002 509,778 Change in net unrealized gains (losses) on investments ............................................... 41,804 5,781 32,986 147,822 169,964 Fixed maturities and short-term investments ........................................................................ (90,312) 7,227 (137,483) 70,496 72,771 TS Hamilton Fund ...................................................................................................................... 132,116 (1,446) 170,469 77,326 97,193 Net realized and unrealized gains (losses) on investments ........................................... 208,526 115,136 587,458 571,964 687,111 Net investment income (loss): Fixed maturities ............................................................................................................................. 36,065 30,070 104,850 82,674 115,869 Short-term investments ................................................................................................................ 3 155 22 453 478 TS Hamilton Fund ......................................................................................................................... 1,507 3,243 5,091 7,837 10,673 Cash and cash equivalents ......................................................................................................... 5,002 3,986 13,491 12,576 16,287 Other ............................................................................................................................................... 781 (575) 1,184 611 1,068 Interest and other ....................................................................................................................... 43,358 36,879 124,638 104,151 144,375 Management fees ....................................................................................................................... (16,432) (13,889) (46,544) (40,574) (55,153) Fixed maturities and short-term investments ........................................................................ (713) (636) (2,222) (1,837) (2,527) TS Hamilton Fund ...................................................................................................................... (15,719) (13,253) (44,322) (38,737) (52,626) Other expenses ........................................................................................................................... (311) (263) (1,010) (856) (1,201) Fixed maturities and short-term investments ........................................................................ (118) (107) (449) (316) (437) TS Hamilton Fund ...................................................................................................................... (193) (156) (561) (540) (764) Net investment income (loss) ................................................................................................. 26,615 22,727 77,084 62,721 88,021 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ......................................................................................................... 235,141 137,863 664,542 634,685 775,132 Net income (loss) attributable to non-controlling interest ....................................................... 146,727 40,225 341,242 220,990 263,359 Total net realized and unrealized gains (losses) on investments and net investment income (loss), net of non-controlling interest .............................................. $ 88,414 $ 97,638 $ 323,300 $ 413,695 $ 511,773 Fixed income, short-term investments and cash and cash equivalents return ................... $ (56,275) $ 43,394 $ (29,923) $ 168,797 $ 210,878 TS Hamilton Fund return(1) .......................................................................................................... $ 144,689 $ 54,244 $ 353,223 $ 244,898 300,895 Summary Consolidated Results Net Investment Return (1) Net of non-controlling interest performance incentive allocation.

10 September 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 ...................................................................... $ 350,678 10% Aa1 $ 797,834 23% Aa1 U.S. states, territories and municipalities ............................................... 9,239 0% Aa2 12,960 0% Aa2 Non-U.S. sovereign governments and supranationals ......................... 92,350 3% Aa1 110,861 3% Aa1 Corporate ..................................................................................................... 1,829,404 50% A3 1,584,144 46% A3 Residential mortgage-backed securities - Agency ................................ 346,377 10% Aa1 365,650 11% Aa1 Residential mortgage-backed securities - Non-agency ....................... 96,434 3% Aa1 32,545 1% Aaa Commercial mortgage-backed securities - Non-agency ...................... 84,482 2% Aa1 94,698 3% Aa1 Other asset-backed securities .................................................................. 348,961 10% Aa1 239,851 7% Aa1 Total fixed maturities .................................................................................. 3,157,925 88% A1 3,238,543 94% Aa3 Short-term investments ................................................................................ 424,046 12% Aa1 200,459 6% Aa1 Total fixed maturities and short-term investments ................................. $ 3,581,971 100% 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) September 30, 2026 December 31, 2025 Average credit quality ................................................................................... A1 Aa3 Average yield to maturity ............................................................................. 5.6% 4.1% Book yield ....................................................................................................... 4.8% 4.3% Expected average duration (in years) ....................................................... 3.8 3.4 (1) Includes $423.5 million and $199.0 million of short-term investments, at September 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 September 30, 2026 Three Months Ended September 30, 2025 ($ in thousands) International Bermuda Total International Bermuda Total Gross premiums written ........................................................................ $ 456,332 $ 363,370 $ 819,702 $ 379,957 $ 318,888 $ 698,845 Net premiums written ............................................................................. 349,250 277,472 626,722 304,410 274,571 578,981 Net premiums earned ............................................................................ 309,313 281,961 591,274 252,302 270,697 522,999 Third party fee income ........................................................................... 1,618 1,194 2,812 2,137 2,032 4,169 Losses and loss adjustment expenses ............................................... 169,916 196,810 366,726 133,895 144,817 278,712 Acquisition costs ..................................................................................... 85,920 65,052 150,972 67,007 58,405 125,412 Other underwriting expenses ................................................................ 46,136 14,725 60,861 41,703 17,252 58,955 Underwriting income (loss) ................................................................... $ 8,959 $ 6,568 $ 15,527 $ 11,834 $ 52,255 $ 64,089 Key Ratios: Attritional loss ratio - current year ........................................................ 54.5 % 60.8 % 57.5 % 55.3 % 55.6 % 55.4 % Attritional loss ratio - prior year development .................................... (3.2) % (6.1) % (4.6) % (2.2) % (2.1) % (2.1) % Catastrophe loss ratio - current year ................................................... 2.2 % 0.0 % 1.1 % 0.0 % 0.0 % 0.0 % Catastrophe loss ratio - prior year development ............................... 1.4 % 15.1 % 8.0 % 0.0 % 0.0 % 0.0 % Loss and loss adjustment expense ratio ............................................ 54.9 % 69.8 % 62.0 % 53.1 % 53.5 % 53.3 % Acquisition cost ratio .............................................................................. 27.8 % 23.1 % 25.5 % 26.6 % 21.6 % 24.0 % Other underwriting expense ratio ......................................................... 14.4 % 4.8 % 9.8 % 15.7 % 5.6 % 10.5 % Combined ratio ........................................................................................ 97.1 % 97.7 % 97.3 % 95.4 % 80.7 % 87.8 % Segment Results Consolidated Underwriting Results

12 Nine Months Ended September 30, 2026 Nine Months Ended September 30, 2025 ($ in thousands) International Bermuda Total International Bermuda Total Gross premiums written ......................................................................... $ 1,319,314 $ 1,271,540 $ 2,590,854 $ 1,094,715 $ 1,159,462 $ 2,254,177 Net premiums written .............................................................................. 959,530 942,547 1,902,077 791,473 947,696 1,739,169 Net premiums earned ............................................................................. 902,728 845,069 1,747,797 746,078 787,012 1,533,090 Third party fee income ............................................................................ 5,985 7,481 13,466 10,301 3,544 13,845 Losses and loss adjustment expenses ................................................ 508,045 544,955 1,053,000 404,300 539,575 943,875 Acquisition costs ...................................................................................... 247,411 193,491 440,902 195,480 169,628 365,108 Other underwriting expenses ................................................................ 128,193 36,947 165,140 116,833 47,831 164,664 Underwriting income (loss) .................................................................... $ 25,064 $ 77,157 $ 102,221 $ 39,766 $ 33,522 $ 73,288 Key Ratios: Attritional loss ratio - current year ......................................................... 53.5 % 56.9 % 55.1 % 53.1 % 53.9 % 53.4 % Attritional loss ratio - prior year development ..................................... (2.2) % 0.7 % (0.8) % (2.9) % (0.8) % (1.8) % Catastrophe loss ratio - current year .................................................... 4.5 % 1.4 % 3.0 % 4.1 % 17.7 % 11.1 % Catastrophe loss ratio - prior year development ................................ 0.5 % 5.5 % 2.9 % (0.1) % (2.2) % (1.1) % Loss and loss adjustment expense ratio ............................................. 56.3 % 64.5 % 60.2 % 54.2 % 68.6 % 61.6 % Acquisition cost ratio ............................................................................... 27.4 % 22.9 % 25.2 % 26.2 % 21.6 % 23.8 % Other underwriting expense ratio ......................................................... 13.5 % 3.5 % 8.7 % 14.3 % 5.6 % 9.8 % Combined ratio ........................................................................................ 97.2 % 90.9 % 94.1 % 94.7 % 95.8 % 95.2 % Segment Results Consolidated Underwriting Results

13 Three Months Ended Nine Months Ended Year Ended September 30, June 30, March 31, December 31, September 30, September 30, September 30, December 31, ($ in thousands) 2026 2026 2026 2025 2025 2026 2025 2025 Gross premiums written ............................................. $ 819,702 $ 831,041 $ 940,110 $ 668,968 $ 698,845 $ 2,590,854 $ 2,254,177 $ 2,923,145 Net premiums written ................................................. 626,722 621,695 653,659 548,373 578,981 1,902,077 1,739,169 2,287,543 Net premiums earned ................................................ 591,274 586,007 570,515 576,686 522,999 1,747,797 1,533,090 2,109,776 Third party fee income ............................................... 2,812 3,904 6,750 12,756 4,169 13,466 13,845 26,601 Losses and loss adjustment expenses ................... 366,726 361,489 324,785 314,646 278,712 1,053,000 943,875 1,258,521 Acquisition costs ......................................................... 150,972 145,423 144,507 142,181 125,412 440,902 365,108 507,290 Other underwriting expenses .................................... 60,861 53,887 50,392 57,079 58,955 165,140 164,664 221,743 Underwriting income (loss) ........................................ $ 15,527 $ 29,112 $ 57,581 $ 75,536 $ 64,089 $ 102,221 $ 73,288 $ 148,823 Key Ratios: Attritional loss ratio - current year ............................ 57.5 % 53.3 % 54.5 % 56.5 % 55.4 % 55.1 % 53.4 % 54.4 % Attritional loss ratio - prior year development ......... (4.6) % (0.1) % 2.4 % (3.1) % (2.1) % (0.8) % (1.8) % (2.2) % Catastrophe loss ratio - current year ....................... 1.1 % 7.8 % 0.0 % 1.4 % 0.0 % 3.0 % 11.1 % 8.4 % Catastrophe loss ratio - prior year development .... 8.0 % 0.7 % 0.0 % (0.2) % 0.0 % 2.9 % (1.1) % (0.9) % Loss and loss adjustment expense ratio ................. 62.0 % 61.7 % 56.9 % 54.6 % 53.3 % 60.2 % 61.6 % 59.7 % Acquisition cost ratio .................................................. 25.5 % 24.8 % 25.3 % 24.7 % 24.0 % 25.2 % 23.8 % 24.0 % Other underwriting expense ratio ............................. 9.8 % 8.5 % 7.6 % 7.7 % 10.5 % 8.7 % 9.8 % 9.2 % Combined ratio ............................................................ 97.3 % 95.0 % 89.8 % 87.0 % 87.8 % 94.1 % 95.2 % 92.9 % Gross premiums written Property ........................................................................ $ 138,880 $ 183,986 $ 248,234 $ 76,203 $ 134,626 $ 571,101 $ 619,717 $ 695,920 Casualty ....................................................................... 441,828 409,517 397,430 379,830 377,483 1,248,775 1,015,025 1,394,855 Specialty ....................................................................... 238,994 237,538 294,446 212,935 186,736 770,978 619,435 832,370 Total ............................................................................ $ 819,702 $ 831,041 $ 940,110 $ 668,968 $ 698,845 $ 2,590,854 $ 2,254,177 $ 2,923,145 Net premiums earned Property ........................................................................ $ 129,026 $ 117,868 $ 126,825 $ 125,109 $ 130,248 $ 373,720 $ 395,440 $ 520,549 Casualty ....................................................................... 283,392 291,401 265,978 261,562 243,997 840,771 693,716 955,278 Specialty ....................................................................... 178,856 176,738 177,712 190,015 148,754 533,306 443,934 633,949 Total ............................................................................ $ 591,274 $ 586,007 $ 570,515 $ 576,686 $ 522,999 $ 1,747,797 $ 1,533,090 $ 2,109,776 Segment Results 5Q Consolidated Underwriting Results - Group

14 Three Months Ended Nine Months Ended Year Ended September 30, June 30, March 31, December 31, September 30, September 30, September 30, December 31, ($ in thousands) 2026 2026 2026 2025 2025 2026 2025 2025 Gross premiums written ............................................. $ 456,332 $ 420,073 $ 442,908 $ 422,345 $ 379,957 $ 1,319,314 $ 1,094,715 $ 1,517,060 Net premiums written ................................................. 349,250 322,843 287,436 340,588 304,410 959,530 791,473 1,132,061 Net premiums earned ................................................ 309,313 302,623 290,791 309,299 252,302 902,728 746,078 1,055,377 Third party fee income ............................................... 1,618 1,820 2,546 1,726 2,137 5,985 10,301 12,027 Losses and loss adjustment expenses ................... 169,916 174,274 163,855 166,998 133,895 508,045 404,300 571,298 Acquisition costs ......................................................... 85,920 80,287 81,204 81,195 67,007 247,411 195,480 276,676 Other underwriting expenses .................................... 46,136 40,758 41,299 50,388 41,703 128,193 116,833 167,221 Underwriting income (loss) ........................................ $ 8,959 $ 9,124 $ 6,979 $ 12,444 $ 11,834 $ 25,064 $ 39,766 $ 52,209 Key Ratios: Attritional loss ratio - current year ............................ 54.5 % 51.1 % 54.9 % 56.3 % 55.3 % 53.5 % 53.1 % 54.0 % Attritional loss ratio - prior year development ......... (3.2) % (4.6) % 1.4 % (2.3) % (2.2) % (2.2) % (2.9) % (2.8) % Catastrophe loss ratio - current year ....................... 2.2 % 11.1 % 0.0 % 0.0 % 0.0 % 4.5 % 4.1 % 2.9 % Catastrophe loss ratio - prior year development .... 1.4 % 0.0 % 0.0 % 0.0 % 0.0 % 0.5 % (0.1) % 0.0 % Loss and loss adjustment expense ratio ................. 54.9 % 57.6 % 56.3 % 54.0 % 53.1 % 56.3 % 54.2 % 54.1 % Acquisition cost ratio .................................................. 27.8 % 26.5 % 27.9 % 26.3 % 26.6 % 27.4 % 26.2 % 26.2 % Other underwriting expense ratio ............................. 14.4 % 12.9 % 13.3 % 15.7 % 15.7 % 13.5 % 14.3 % 14.7 % Combined ratio ............................................................ 97.1 % 97.0 % 97.5 % 96.0 % 95.4 % 97.2 % 94.7 % 95.0 % Gross premiums written Property ........................................................................ $ 71,356 $ 61,292 $ 54,496 $ 55,276 $ 63,894 $ 187,145 $ 182,292 $ 237,568 Casualty ....................................................................... 192,462 175,394 166,577 185,152 167,107 534,433 443,110 628,262 Specialty ....................................................................... 192,514 183,387 221,835 181,917 148,956 597,736 469,313 651,230 Total ............................................................................ $ 456,332 $ 420,073 $ 442,908 $ 422,345 $ 379,957 $ 1,319,314 $ 1,094,715 $ 1,517,060 Net premiums earned Property ........................................................................ $ 56,211 $ 48,191 $ 50,586 $ 47,772 $ 47,813 $ 154,989 $ 137,223 $ 184,995 Casualty ....................................................................... 111,207 115,845 99,880 104,188 91,841 326,932 271,643 375,831 Specialty ....................................................................... 141,895 138,587 140,325 157,339 112,648 420,807 337,212 494,551 Total ............................................................................ $ 309,313 $ 302,623 $ 290,791 $ 309,299 $ 252,302 $ 902,728 $ 746,078 $ 1,055,377 Segment Results 5Q Underwriting Results - International

15 Three Months Ended Nine Months Ended Year Ended September 30, June 30, March 31, December 31, September 30, September 30, September 30, December 31, ($ in thousands) 2026 2026 2026 2025 2025 2026 2025 2025 Gross premiums written ............................................. $ 363,370 $ 410,968 $ 497,202 $ 246,623 $ 318,888 $ 1,271,540 $ 1,159,462 $ 1,406,085 Net premiums written ................................................. 277,472 298,852 366,223 207,785 274,571 942,547 947,696 1,155,482 Net premiums earned ................................................ 281,961 283,384 279,724 267,387 270,697 845,069 787,012 1,054,399 Third party fee income ............................................... 1,194 2,084 4,204 11,030 2,032 7,481 3,544 14,574 Losses and loss adjustment expenses ................... 196,810 187,215 160,930 147,648 144,817 544,955 539,575 687,223 Acquisition costs ......................................................... 65,052 65,136 63,303 60,986 58,405 193,491 169,628 230,614 Other underwriting expenses .................................... 14,725 13,129 9,093 6,691 17,252 36,947 47,831 54,522 Underwriting income (loss) ........................................ $ 6,568 $ 19,988 $ 50,602 $ 63,092 $ 52,255 $ 77,157 $ 33,522 $ 96,614 Key Ratios: Attritional loss ratio - current year ............................ 60.8 % 55.7 % 53.9 % 56.7 % 55.6 % 56.9 % 53.9 % 54.6 % Attritional loss ratio - prior year development ......... (6.1) % 4.6 % 3.6 % (4.1) % (2.1) % 0.7 % (0.8) % (1.6) % Catastrophe loss ratio - current year ....................... 0.0 % 4.3 % 0.0 % 3.0 % 0.0 % 1.4 % 17.7 % 13.9 % Catastrophe loss ratio - prior year development .... 15.1 % 1.5 % 0.0 % (0.4) % 0.0 % 5.5 % (2.2) % (1.7) % Loss and loss adjustment expense ratio ................. 69.8 % 66.1 % 57.5 % 55.2 % 53.5 % 64.5 % 68.6 % 65.2 % Acquisition cost ratio .................................................. 23.1 % 23.0 % 22.6 % 22.8 % 21.6 % 22.9 % 21.6 % 21.9 % Other underwriting expense ratio ............................. 4.8 % 3.9 % 1.7 % (1.6) % 5.6 % 3.5 % 5.6 % 3.8 % Combined ratio ............................................................ 97.7 % 93.0 % 81.8 % 76.4 % 80.7 % 90.9 % 95.8 % 90.9 % Gross premiums written Property ........................................................................ $ 67,524 $ 122,694 $ 193,738 $ 20,927 $ 70,732 $ 383,956 $ 437,425 $ 458,352 Casualty ....................................................................... 249,366 234,123 230,853 194,678 210,376 714,342 571,915 766,593 Specialty ....................................................................... 46,480 54,151 72,611 31,018 37,780 173,242 150,122 181,140 Total ............................................................................ $ 363,370 $ 410,968 $ 497,202 $ 246,623 $ 318,888 $ 1,271,540 $ 1,159,462 $ 1,406,085 Net premiums earned Property ........................................................................ $ 72,815 $ 69,677 $ 76,239 $ 77,337 $ 82,435 $ 218,731 $ 258,217 $ 335,554 Casualty ....................................................................... 172,185 175,556 166,098 157,374 152,156 513,839 422,073 579,447 Specialty ....................................................................... 36,961 38,151 37,387 32,676 36,106 112,499 106,722 139,398 Total ............................................................................ $ 281,961 $ 283,384 $ 279,724 $ 267,387 $ 270,697 $ 845,069 $ 787,012 $ 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 $ 229.9 7.8 % Northeast U.S. Hurricane 1 in 100 208.9 7.1 % Gulf (TX - AL) U.S. Hurricane 1 in 100 194.2 6.6 % California Earthquake 1 in 250 317.2 10.8 % Pacific Northwest Earthquake 1 in 250 149.6 5.1 % (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 October 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 ............................................... 11.3 % 20.9 % 16.6 % 21.6 % 22.4 % Adjustment for: Net realized (gains) losses on investments - Fixed maturity and short-term investments(1) ................................................................................................................ 1.0 % (0.5) % 0.4 % (0.2) % (0.3) % Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1) ................................................................................................................ 12.5 % (1.1) % 6.4 % (3.7) % (2.8) % Net foreign exchange (gains) losses ............................................................................................ 0.1 % (0.4) % — % 0.2 % 0.2 % Operating return on average common shareholders' equity - annualized .............................. 24.9 % 18.9 % 23.4 % 17.9 % 19.5 % Other Information Non-GAAP Measures Net income (loss) and other comprehensive income (loss) attributable to common shareholders per common share - diluted ................................................................... $ 0.81 $ 1.32 $ 3.54 $ 3.88 $ 5.55 Adjustment for: Net realized (gains) losses on investments - Fixed maturity and short-term investments(1) ................................................................................................................ 0.07 (0.03) 0.09 (0.04) (0.07) Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1) ................................................................................................................ 0.89 (0.07) 1.36 (0.68) (0.70) Net foreign exchange (gains) losses ............................................................................................ 0.01 (0.02) (0.01) 0.04 0.06 Operating income (loss) attributable to common shareholders per common share - diluted .................................................................................................................. $ 1.78 $ 1.20 $ 4.98 $ 3.20 $ 4.84 Three Months Ended September 30, Nine Months Ended September 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 .................................................................................................................... $ 81,456 $ 136,200 $ 358,776 $ 404,486 $ 576,670 Adjustment for: Net realized (gains) losses on investments - Fixed maturity and short-term investments(1) ................................................................................................................ 6,983 (3,274) 9,316 (4,140) (7,369) Net unrealized (gains) losses on investments - Fixed maturity and short-term investments(1) ................................................................................................................ 90,312 (7,227) 137,483 (70,496) (72,771) Net foreign exchange (gains) losses ............................................................................................ 1,188 (2,619) $ (719) $ 4,422 $ 5,985 Operating income (loss) attributable to common shareholders ............................................... $ 179,939 $ 123,080 $ 504,856 $ 334,272 $ 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 September 30, Nine Months Ended September 30, Year Ended ($ in thousands) 2026 2025 2026 2025 2025 Underwriting income (loss) ............................................................................................................. $ 15,527 $ 64,089 $ 102,221 $ 73,288 $ 148,823 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ......................................................................................................... 235,141 137,863 664,542 634,685 775,132 Net foreign exchange gains (losses) ............................................................................................ (1,188) 2,619 719 (4,422) (5,985) Corporate expenses ........................................................................................................................ (14,097) (15,347) (38,213) (41,168) (57,167) Amortization of intangible assets .................................................................................................. (3,762) (4,000) (11,482) (11,895) (15,709) Interest expense .............................................................................................................................. (4,801) (4,933) (14,339) (15,264) (20,189) Income tax (expense) benefit ........................................................................................................ 1,363 (3,866) (3,430) (9,748) 15,124 Net income (loss), prior to non-controlling interest ..................................................................... $ 228,183 $ 176,425 $ 700,018 $ 625,476 $ 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 September 30, Nine Months Ended September 30, Year Ended ($ in thousands) 2026 2025 2026 2025 2025 Third party fee income .................................................................................................................... $ 2,812 $ 4,169 $ 13,466 $ 13,845 $ 26,601 Other income (loss) ......................................................................................................................... $ 2,812 $ 4,169 $ 13,466 $ 13,845 $ 26,601

20 Three Months Ended September 30, Nine Months Ended September 30, Year Ended ($ in thousands) 2026 2025 2026 2025 2025 Other underwriting expenses ......................................................................................................... $ 60,861 $ 58,955 $ 165,140 $ 164,664 $ 221,743 Corporate expenses ........................................................................................................................ 14,097 15,347 38,213 41,168 57,167 General and administrative expenses .......................................................................................... $ 74,958 $ 74,302 $ 203,353 $ 205,832 $ 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 3Q 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 po sition, 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 materia lly 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 $2.6B 9M 2026 Gross Premiums Written (GPW) $149m FY 2025 $102m 9M 2026 Underwriting Income 92.9% FY 2025 94.1% 9M 2026 Combined Ratio $6.4B 3Q 2026 Cash & Invested Assets $2.9B 3Q 2026 Shareholders’ Equity $577m FY 2025 $359m 9M 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% 62% 60% 38% 37% 36% 33% 33% 34% 34% 106% 103% 90% 91% 93% 95% 94% 2021 2022 2023 2024 2025 9M 2025 9M 2026 $1,447 $1,647 $1,951 $2,423 $2,923 $2,254 $2,591 2021 2022 2023 2024 2025 9M 2025 9M 2026 Hamilton Group - Gross Premiums Written ($’m) Hamilton Group - Combined Ratio(2) Loss Ratio Expense Ratio (1) Compound annual growth rate, (2) Numbers may not add due to rounding.

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. carrier platform for domestically placed, wholesale only, small to mid-size property and casualty risks 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% 54% 56% 44% 43% 43% 39% 41% 41% 41% 108% 97% 95% 96% 95% 95% 97% 2021 2022 2023 2024 2025 9M 2025 9M 2026 $892 $933 $1,106 $1,308 $1,517 $1,095 $1,319 2021 2022 2023 2024 2025 9M 2025 9M 2026 International Segment - Gross Premiums Written ($’m) International Segment - Combined Ratio(2) Loss Ratio Expense Ratio (1) Compound annual growth rate, (2) Numbers may not add due to rounding.

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% 69% 65% 29% 29% 28% 27% 26% 27% 26% 104% 110% 85% 87% 91% 96% 91% 2021 2022 2023 2024 2025 9M 2025 9M 2026 $554 $713 $846 $1,114 $1,406 $1,159 $1,272 2021 2022 2023 2024 2025 9M 2025 9M 2026 Bermuda Segment - Gross Premiums Written ($’m) Bermuda Segment - Combined Ratio(2) Loss Ratio Expense Ratio (1) Compound annual growth rate, (2) Numbers may not add due to rounding.

Invested Assets

16 Investment Strategy Review – $6.4 Billion Invested Assets Investment Portfolio as of September 30, 2026 PRESERVATION OF CAPITAL LIQUIDITY DIVERSIFICATION ATTRACTIVE RETURNS RISK MANAGEMENT & GOVERNANCE A1 average credit quality 100% investment grade Highly liquid Market sector diversification 4.8% book yield As at 9/30/2026 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 13.5% 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% / $3.9B Two Sigma Hamilton Fund 39% / $2.5B *Investment management agreement

17 Fixed Income Investment Portfolio as of September 30, 2026 Invested Assets 58% 11% 11% 20% Corporate US Treasury US Agency Other $3.2B Corporate A3 US Treas. Aa1 US Agency Aa1 Other Aa1 Fixed income investments of $3.2 billion – Average rating of A1 and duration of 3.8 years Yield to Maturity: 5.6%

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 $90B 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 $2.5B TSHF as of September 30, 2026 13.5% Average annualized returns 2014-3Q 2026 Dedicated fund of one Allocation 70% equities 30% macro Highly liquid Investments TSHF Returns Since 2021 1.49 Sharpe Ratio since inception 17.7% 4.6% 7.6% 16.3% 16.0% 16.3% 2021 2022 2023 2024 2025 9M 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 $29.80 $2.00 3Q23 4Q23 1Q24 2Q24 3Q24 4Q24 1Q25 2Q25 3Q25 4Q25 1Q26 2Q26 3Q26 Book Value Per Share ("BVPS") + Accumulated Dividend Growth Since IPO BVPS Accumulated Dividends A Value Creation Engine: 83% 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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