Form 8-K - Current report

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

May 8, 2024

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 May 8, 2024, Hamilton Insurance Group, Ltd. (the “Company”) issued a press release announcing its financial results for the quarter ended March 31, 2024 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.

As provided in General Instruction B.2 of Form 8-K, the information and exhibits in this report are being “furnished” and shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to liability under that section, nor shall they be deemed to be incorporated by reference into any filing or other document under the Securities Act of 1933, as amended, or the Exchange Act, except as shall be expressly set forth by specific reference in such filing or document.

Item 9.01 - Financial Statements and Exhibits

(d):The following exhibits are being filed herewith:


Exhibit No.						Description
99.1						Press Release, dated May 8, 2024, issued by Hamilton Insurance Group, Ltd.
99.2						Supplementary Financial Information - March 31, 2024
99.3						Investor Presentation - March 31, 2024
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: May 8, 2024.


			HAMILTON INSURANCE GROUP, LTD.

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

Hamilton Reports 2024 First Quarter Results

Net Income of $157 Million; Six Consecutive Quarters of Underwriting Income

PEMBROKE, Bermuda, May 8, 2024 – Hamilton Insurance Group, Ltd. (NYSE: HG; “Hamilton” or “the Company”) today announced financial results for the first quarter ended March 31, 2024.

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

“I am very proud of Hamilton’s financial results for the first quarter. Not only did we generate strong underwriting and investment returns but also, this quarter marks our sixth consecutive quarter of underwriting profitability. I am also extremely pleased about our ability to take advantage of market opportunities with another quarter of double-digit growth, a momentum we expect will be enhanced by our recent AM Best ratings upgrade.”

Consolidated Highlights – First Quarter

•Net income of $157.2 million;

•Annualized return on average equity of 29.5%;

•Gross premiums written of $721.9 million, an increase of 34.1% compared to the first quarter of 2023;

•Net premiums earned of $385.3 million, an increase of 35.7% compared to the first quarter of 2023;

•Combined ratio of 91.5%;

•Underwriting income of $32.5 million;

•Net investment income of $147.8 million, comprised of Two Sigma Hamilton Fund returns of $142.7 million and fixed income, short term, cash and cash equivalent returns of $5.2 million; and

•Corporate expenses of $11.5 million, which includes $3.7 million of compensation costs related to the Value Appreciation Pool.


	For the Three Months Ended
($ in thousands, except for per share amounts and percentages)	March 31, 2024		March 31, 2023		Change
Gross premiums written	$	721,941	$	538,164	$	183,777
Net premiums written	514,880		348,498		166,382
Net premiums earned	385,303		283,902		101,401
Underwriting income (loss)	$	32,522	$	34,063	$	(1,541)
Combined ratio	91.5%		87.9%		3.6 pts

Net income (loss) attributable to common shareholders	$	157,174	$	51,492	$	105,682
Income (loss) per share attributable to common shareholders - diluted	$	1.38	$	0.49
Book value per common share	$	19.90	$	16.55
Change in book value per common share	7.1%		2.5%

Return on average common equity - annualized	29.5%		12.2%


	For the Three Months Ended
Key Ratios	March 31, 2024		March 31, 2023		Change
Attritional loss ratio - current year	57.2	%	49.1	%	8.1	pts
Attritional loss ratio - prior year	3.1	%	0.6	%	2.5	pts
Catastrophe loss ratio - current year	0.0	%	1.8	%	(1.8	pts)
Catastrophe loss ratio - prior year	0.0	%	0.8	%	(0.8	pts)
Loss and loss adjustment expense ratio	60.3	%	52.3	%	8.0	pts
Acquisition cost ratio	21.9	%	22.9	%	(1.0	pts)
Other underwriting expense ratio	9.3	%	12.7	%	(3.4	pts)
Combined ratio	91.5	%	87.9	%	3.6	pts

•Gross premiums written increased by $183.8 million, or 34.1%, to $721.9 million with an increase of $73.7 million, or 29.8% in the International Segment, and $110.1 million, or 37.8% in the Bermuda Segment.

•Net premiums written increased by $166.4 million, or 47.7%, to $514.9 million with an increase of $63.0 million, or 51.6% in the International Segment, and $103.4 million, or 45.6% in the Bermuda Segment.

•Net premiums earned increased by $101.4 million, or 35.7%, to $385.3 million with an increase of $47.3 million, or 31.6% in the International Segment, and $54.1 million, or 40.3% in the Bermuda Segment.

•The attritional loss ratio (current year), net of reinsurance, was 57.2%. The increase of 8.1 points compared to the same period in 2023 was primarily driven by losses of $37.9 million, or 9.8 points, arising from the Francis Scott Key Baltimore Bridge collapse, corresponding to the high end of the industry loss estimates that range from $1 billion to $3 billion.

•Net unfavorable attritional prior year reserve development, net of reinsurance, was $11.9 million, primarily driven by two specific large losses on our specialty insurance and reinsurance classes.

•Catastrophe losses (current and prior year), net of reinsurance, were $0.2 million.

•The acquisition cost ratio decreased by 1.0 point compared to same period in 2023.

•The other underwriting expense ratio decreased 3.4 points compared to the same period in 2023, primarily driven by an increase in net premiums earned.

Segment Underwriting Results – First Quarter


International Segment	For the Three Months Ended
($ in thousands, except for percentages)	March 31, 2024			March 31, 2023			Change
Gross premiums written	$	320,841		$	247,114		$	73,727
Net premiums written	185,033			122,019			63,014
Net premiums earned	196,814			149,515			47,299
Underwriting income (loss)	$	5,315		$	16,370		$	(11,055)

Key Ratios
Attritional loss ratio - current year	56.0		%	49.9		%	6.1		pts
Attritional loss ratio - prior year	2.9		%	(4.2		%)	7.1		pts
Catastrophe loss ratio - current year	0.0		%	0.0		%	0.0		pts
Catastrophe loss ratio - prior year	0.1		%	1.4		%	(1.3		pts)
Loss and loss adjustment expense ratio	59.0		%	47.1		%	11.9		pts
Acquisition cost ratio	24.2		%	24.9		%	(0.7		pts)
Other underwriting expense ratio	14.0		%	17.1		%	(3.1		pts)
Combined ratio	97.2		%	89.1		%	8.1		pts

•Gross premiums written increased by $73.7 million, or 29.8%, to $320.8 million, primarily driven by growth and improved pricing in specialty reinsurance and casualty and property insurance classes.

•The attritional loss ratio (current year), net of reinsurance, was 56.0%. The increase of 6.1 points compared to the same period in 2023 was primarily driven by net losses of $11.8 million, or 6.0 points, arising from the Baltimore Bridge collapse.

•Net unfavorable attritional prior year reserve development, net of reinsurance, was $5.8 million, primarily driven by two specific large losses on our specialty insurance class.

•Catastrophe losses (current and prior year), net of reinsurance, were $0.2 million.

•The acquisition cost ratio decreased by 0.7 points compared to the same period in 2023.

•The other underwriting expense ratio decreased by 3.1 points compared to the same period in 2023, primarily driven by an increase in net premiums earned.


Bermuda Segment	For the Three Months Ended
($ in thousands, except for percentages)	March 31, 2024			March 31, 2023			Change
Gross premiums written	$	401,100		$	291,050		$	110,050
Net premiums written	329,847			226,479			103,368
Net premiums earned	188,489			134,387			54,102
Underwriting income (loss)	$	27,207		$	17,693		$	9,514

Key Ratios
Attritional loss ratio - current year	58.4		%	48.1		%	10.3		pts
Attritional loss ratio - prior year	3.2		%	6.1		%	(2.9		pts)
Catastrophe loss ratio - current year	0.0		%	3.9		%	(3.9		pts)
Catastrophe loss ratio - prior year	0.0		%	0.1		%	(0.1		pts)
Loss and loss adjustment expense ratio	61.6		%	58.2		%	3.4		pts
Acquisition cost ratio	19.5		%	20.8		%	(1.3		pts)
Other underwriting expense ratio	4.4		%	7.9		%	(3.5		pts)
Combined ratio	85.5		%	86.9		%	(1.4		pts)

•Gross premiums written increased by $110.1 million, or 37.8%, to $401.1 million, primarily attributable to new business, increased participation on existing business and a strong rate environment across multiple classes of business.

•The attritional loss ratio (current year), net of reinsurance, was 58.4%. The increase of 10.3 points compared to the same period in 2023 was primarily driven by net losses of $26.1 million, or 13.8 points, arising from the Baltimore Bridge collapse.

•Net unfavorable attritional prior year reserve development, net of reinsurance, was $6.1 million, primarily driven by a specific large loss in our specialty reinsurance class.

•Catastrophe losses (current and prior year), net of reinsurance, were $Nil.

•The acquisition cost ratio decreased by 1.3 points compared to the same period in 2023.

•The other underwriting expense ratio decreased by 3.5 points compared to the same period in 2023. The decrease was primarily driven by an increase in net premiums earned and by performance based management fees generated by our third party capital manager.

Investments and Shareholders’ Equity as of March 31, 2024

•Total invested assets and cash of $4.2 billion compared to $4.0 billion at December 31, 2023.

•Total shareholders’ equity of $2.2 billion compared to $2.0 billion at December 31, 2023.

•Book value per share of $19.90 compared to $18.58 at December 31, 2023, an increase of 7.1%.

Conference Call Details and Additional Information

Conference Call Information

Hamilton will host a conference call to discuss its financial results on Thursday, May 9, 2024, at 10:00 a.m. ET. The conference call can be accessed by dialing 1-888-350-3870 (US toll free), or 1-646-960-0308, and entering the conference ID 6439207.

A live, audio webcast of the conference call will also be available through the Investors portal of the Company’s website at investors.hamiltongroup.com.

For access to either the conference call or webcast, please dial in/login a few minutes in advance to complete any necessary registration.

A replay of the audio conference call will be available at investors.hamiltongroup.com or by dialing 1-800-770-2030 (US toll free) and entering the conference ID 6439207.

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

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

Consolidated Balance Sheet


($ in thousands)	March 31, 2024		December 31, 2023
Assets
Fixed maturity investments, at fair value (amortized cost 2024: $1,926,329; 2023: $1,867,499)	$	1,877,130	$	1,831,268
Short-term investments, at fair value (amortized cost 2024: $351,035; 2023: $427,437)	352,068		428,878
Investments in Two Sigma Funds, at fair value (cost 2024: $753,967; 2023: $770,191)	953,659		851,470
Total investments	3,182,857		3,111,616
Cash and cash equivalents	1,085,038		794,509
Restricted cash and cash equivalents	95,565		106,351
Premiums receivable	856,111		658,363
Paid losses recoverable	169,469		145,202
Deferred acquisition costs	190,883		156,895
Unpaid losses and loss adjustment expenses recoverable	1,167,504		1,161,077
Receivables for investments sold	17,777		42,419
Prepaid reinsurance	285,984		194,306
Intangible assets	92,651		90,996
Other assets	205,186		209,621
Total assets	$	7,349,025	$	6,671,355

Liabilities, non-controlling interest, and shareholders' equity
Liabilities
Reserve for losses and loss adjustment expenses	$	3,148,782	$	3,030,037
Unearned premiums	1,132,477		911,222
Reinsurance balances payable	367,123		272,310
Payables for investments purchased	55,071		66,606
Term loan, net of issuance costs	149,859		149,830
Accounts payable and accrued expenses	155,684		186,887
Payables to related parties	75,797		6,480
Total liabilities	5,084,793		4,623,372

Non-controlling interest – TS Hamilton Fund	54,727		133

Shareholders’ equity
Common shares:
Class A, authorized (2024 and 2023: 28,644,807), par value $0.01; issued and outstanding (2024 and 2023: 28,644,807)	286		286
Class B, authorized (2024 and 2023: $72,337,352), par value $0.01; issued and outstanding (2024 $56,813,977 and 2023: 56,036,067)	568		560
Class C, authorized (2024 and 2023: 25,544,229), par value $0.01; issued and outstanding (2024 and 2023: 25,544,229)	255		255
Additional paid-in capital	1,255,055		1,249,817
Accumulated other comprehensive loss	(4,441)		(4,441)
Retained earnings	957,782		801,373
Total shareholders' equity	2,209,505		2,047,850

Total liabilities, non-controlling interest, and shareholders' equity	$	7,349,025	$	6,671,355

Consolidated Statement of Operations


	Three Months Ended
	March 31,
($ in thousands, except per share information)	2024		2023
Revenues
Gross premiums written	$	721,941	$	538,164
Reinsurance premiums ceded	(207,061)		(189,666)
Net premiums written	514,880		348,498

Net change in unearned premiums	(129,577)		(64,596)
Net premiums earned	385,303		283,902

Net realized and unrealized gains (losses) on investments	255,371		35,133
Net investment income (loss)	12,618		2,359
Total net realized and unrealized gains (losses) on investments and net investment income (loss)	267,989		37,492


Other income (loss)	7,478		3,033
Net foreign exchange gains (losses)	(2,125)		(2,046)
Total revenues	658,645		322,381

Expenses
Losses and loss adjustment expenses	232,352		148,561
Acquisition costs	84,554		65,140
General and administrative expenses	54,855		45,806

Amortization of intangible assets	3,252		2,770
Interest expense	5,708		5,529
Total expenses	380,721		267,806

Income (loss) before income tax	277,924		54,575
Income tax expense (benefit)	592		1,573
Net income (loss)	277,332		53,002

Net income (loss) attributable to non-controlling interest	120,158		1,510

Net income (loss) and other comprehensive income (loss) attributable to common shareholders	$	157,174	$	51,492

Per share data
Basic income (loss) per share attributable to common shareholders	$	1.42	$	0.50
Diluted income (loss) per share attributable to common shareholders	$	1.38	$	0.49

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 are considered non-GAAP financial measures under SEC rules and regulations. In this press release, we present underwriting income (loss), a non-GAAP financial measure as defined in Item 10(e) of SEC Regulation S-K. We believe that 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 comparable GAAP figures 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 following table reconciles underwriting income (loss) to net income (loss), the most comparable GAAP financial measure:


	For the Three Months Ended
($ in thousands)	March 31, 2024		March 31, 2023
Underwriting income (loss)	$	32,522	$	34,063
Total net realized and unrealized gains (losses) on investments and net investment income (loss)	267,989		37,492

Other income (loss), excluding third party fee income	—		29
Net foreign exchange gains (losses)	(2,125)		(2,046)
Corporate expenses	(11,502)		(6,664)

Amortization of intangible assets	(3,252)		(2,770)
Interest expense	(5,708)		(5,529)
Income tax (expense) benefit	(592)		(1,573)
Net income (loss), prior to non-controlling interest	$	277,332	$	53,002

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 fees earned by the International Segment for management services provided to third party syndicates and consortia and by the Bermuda Segment for performance based management fees generated by our third party capital manager, Ada Capital Management Limited. 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 comparable GAAP financial measure:


	For the Three Months Ended
($ in thousands)	March 31, 2024		March 31, 2023
Third party fee income	$	7,478	$	3,004
Other income (loss), excluding third party fee income	—		29
Other income (loss)	$	7,478	$	3,033

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 comparable GAAP financial measure:


	For the Three Months Ended
($ in thousands)	March 31, 2024		March 31, 2023
Other underwriting expenses	$	43,353	$	39,142
Corporate expenses	11,502		6,664
General and administrative expenses	$	54,855	$	45,806

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,” 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 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, 2023 (the “Form 10-K”) and other subsequent periodic reports filed with the Securities and Exchange Commission and the following:

•our results of operations and financial condition could be adversely affected by unpredictable catastrophic events, global climate change or emerging claim and coverage issues;

•our business could be materially adversely affected if we do not accurately assess our underwriting risk, our reserves are inadequate to cover our actual losses, our models or assessments and pricing of risks are incorrect or we lose important broker relationships;

•the insurance and reinsurance business is historically cyclical and the pricing and terms for our products may decline, which would affect our profitability and ability to maintain or grow premiums;

•we have significant foreign operations that expose us to certain additional risks, including foreign currency risks and political risk;

•we do not control the allocations to and/or the performance of the Two Sigma Hamilton Fund, LLC ("TS Hamilton Fund")’s investment portfolio, and its performance depends on the ability of its investment manager, Two Sigma Investments, LP ("Two Sigma"), to select and manage appropriate investments and we have a limited ability to withdraw our capital accounts;

•Two Sigma Principals, LLC, Two Sigma and their respective affiliates have potential conflicts of interest that could adversely affect us;

•the historical performance of Two Sigma is not necessarily indicative of the future results of the TS Hamilton Fund’s investment portfolio or of our future results;

•our ability to manage risks associated with macroeconomic conditions resulting from geopolitical and global economic events, including public health crises, current or anticipated military conflicts, terrorism, sanctions, rising energy prices, inflation and interest rates and other global events;

•our ability to compete successfully with more established competitors and risks relating to consolidation in the reinsurance and insurance industries;

•downgrades, potential downgrades or other negative actions by rating agencies;

•our dependence on key executives, including the potential loss of Bermudian personnel as a result of Bermuda employment restrictions, and the inability to attract qualified personnel, particularly in very competitive hiring conditions;

•our dependence on letter of credit facilities that may not be available on commercially acceptable terms;

•our potential need for additional capital in the future and the potential unavailability of such capital to us on favorable terms or at all;

•the suspension or revocation of our subsidiaries’ insurance licenses;

•risks associated with our investment strategy, including such risks being greater than those faced by competitors;

•changes in the regulatory environment and the potential for greater regulatory scrutiny of the Company going forward;

•a cyclical downturn of the reinsurance industry;

•operational failures, failure of information systems or failure to protect the confidentiality of customer information, including by service providers, or losses due to defaults, errors or omissions by third parties or our affiliates;

•we are a holding company with no direct operations, and our insurance and reinsurance subsidiaries’ ability to pay dividends and other distributions to us is restricted by law;

•risks relating to our ability to identify and execute opportunities for growth or our ability to complete transactions as planned or realize the anticipated benefits of our acquisitions or other investments;

•our potentially becoming subject to U.S. federal income taxation, Bermuda taxation or other taxes as a result of a change of tax laws or otherwise;

•the potential characterization of us and/or any of our subsidiaries as a passive foreign investment company, or PFIC;

•our potentially becoming subject to U.S. withholding and information reporting requirements under the U.S. Foreign Account Tax Compliance Act, or FATCA, provisions;

•our costs will increase as a result of operating as a public company, and our management will be required to devote substantial time to complying with public company regulations;

•if we were to identify a material weakness and were unable to remediate such material weakness, or fail to achieve and maintain effective internal controls, our operating results and financial condition could be impacted and the market price of our Class B common shares may be negatively affected;

•the lack of a prior public market for our Class B common shares means our share price may be volatile and anti-takeover provisions contained in our organizational documents could delay management changes;

•the potential that the market price of our Class B common shares could decline due to future sales of shares by our existing shareholders;

•applicable insurance laws, which could make it difficult to effect a change of control of our company; and

•investors may have difficulties in serving process or enforcing judgments against us in the United States.

There may be other factors that could cause our actual results to differ materially from the forward-looking statements, including factors disclosed under the sections entitled “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” in the Form 10-K. 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 contacts:

Jon Levenson & Darian Niforatos

Investor.Relations@hamiltongroup.com

Media contact:

Kelly Corday Ferris

kelly.ferris@hamiltongroup.com

Hamilton Insurance Group, Ltd. Supplementary Financial Information March 31, 2024 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 .................................................................................................................................................................. 12 5Q Underwriting Results - International ............................................................................................................................................................................... 13 5Q Underwriting Results - Bermuda ..................................................................................................................................................................................... 14 V. Other Information Modeled Exposure to Catastrophe Losses (PML) ............................................................................................................................................................. 15 Non-GAAP Measures .............................................................................................................................................................................................................. 16

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 information is being provided for informational purposes only. It should be read in conjunction with the documents filed by Hamilton Insurance Group, Inc. ("Hamilton") with the U.S Securities and Exchange Commission, including its Form 10-Q. 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,” 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 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, 2023 (the “Form 10-K”) and other subsequent periodic reports filed with the Securities and Exchange Commission and the following: • our results of operations and financial condition could be adversely affected by unpredictable catastrophic events, global climate change or emerging claim and coverage issues; • our business could be materially adversely affected if we do not accurately assess our underwriting risk, our reserves are inadequate to cover our actual losses, our models or assessments and pricing of risks are incorrect or we lose important broker relationships; • the insurance and reinsurance business is historically cyclical and the pricing and terms for our products may decline, which would affect our profitability and ability to maintain or grow premiums; • we have significant foreign operations that expose us to certain additional risks, including foreign currency risks and political risk; • we do not control the allocations to and/or the performance of the Two Sigma Hamilton Fund, LLC ("TS Hamilton Fund")’s investment portfolio, and its performance depends on the ability of its investment manager, Two Sigma Investments, LP (“Two Sigma”), to select and manage appropriate investments and we have a limited ability to withdraw our capital accounts; • Two Sigma Principals, LLC, Two Sigma and their respective affiliates have potential conflicts of interest that could adversely affect us; • the historical performance of Two Sigma is not necessarily indicative of the future results of the TS Hamilton Fund’s investment portfolio or of our future results;

2 Basis of Presentation (continued) Special Note Regarding Forward-Looking Statements (continued) • our ability to manage risks associated with macroeconomic conditions resulting from geopolitical and global economic events, including public health crises, current or anticipated military conflicts, terrorism, sanctions, rising energy prices, inflation and interest rates and other global events; • our ability to compete successfully with more established competitors and risks relating to consolidation in the reinsurance and insurance industries; • downgrades, potential downgrades or other negative actions by rating agencies; • our dependence on key executives, including the potential loss of Bermudian personnel as a result of Bermuda employment restrictions, and the inability to attract qualified personnel, particularly in very competitive hiring conditions; • our dependence on letter of credit facilities that may not be available on commercially acceptable terms; • our potential need for additional capital in the future and the potential unavailability of such capital to us on favorable terms or at all; • the suspension or revocation of our subsidiaries’ insurance licenses; • risks associated with our investment strategy, including such risks being greater than those faced by competitors; • changes in the regulatory environment and the potential for greater regulatory scrutiny of the Company going forward; • a cyclical downturn of the reinsurance industry; • operational failures, failure of information systems or failure to protect the confidentiality of customer information, including by service providers, or losses due to defaults, errors or omissions by third parties or our affiliates; • we are a holding company with no direct operations, and our insurance and reinsurance subsidiaries’ ability to pay dividends and other distributions to us is restricted by law; • risks relating to our ability to identify and execute opportunities for growth or our ability to complete transactions as planned or realize the anticipated benefits of our acquisitions or other investments; • our potentially becoming subject to U.S. federal income taxation, Bermuda taxation or other taxes as a result of a change of tax laws or otherwise; • the potential characterization of us and/or any of our subsidiaries as a passive foreign investment company, or PFIC; • our potentially becoming subject to U.S. withholding and information reporting requirements under the U.S. Foreign Account Tax Compliance Act, or FATCA, provisions; • our costs will increase as a result of operating as a public company, and our management will be required to devote substantial time to complying with public company regulations; • if we were to identify a material weakness and were unable to remediate such material weakness, or fail to achieve and maintain effective internal controls, our operating results and financial condition could be impacted and the market price of our Class B common shares may be negatively affected; • the lack of a prior public market for our Class B common shares means our share price may be volatile and anti-takeover provisions contained in our organizational documents could delay management changes; • the potential that the market price of our Class B common shares could decline due to future sales of shares by our existing shareholders; • applicable insurance laws, which could make it difficult to effect a change of control of our company; and • investors may have difficulties in serving process or enforcing judgments against us in the United States. There may be other factors that could cause our actual results to differ materially from the forward-looking statements, including factors disclosed under the sections entitled “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” in the Form 10-K and other subsequent periodic reports filed with the Securities and Exchange Commission. You should evaluate all forward-looking statements made herein in the context of these risks and uncertainties.

3 Basis of Presentation (continued) Special Note Regarding Forward-Looking Statements (continued) 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 March 31, ($ in thousands) 2024 2023 Net income (loss) attributable to common shareholders ........................................................................................................................................... $ 157,174 $ 51,492 Underwriting income (loss) Gross premiums written .................................................................................................................................................................................................. $ 721,941 $ 538,164 Net premiums written ....................................................................................................................................................................................................... 514,880 348,498 Net premiums earned ...................................................................................................................................................................................................... 385,303 283,902 Underwriting income (loss) ............................................................................................................................................................................................. $ 32,522 $ 34,063 Key Ratios: Attritional loss ratio - current year .................................................................................................................................................................................. 57.2% 49.1% Attritional loss ratio - prior year development .............................................................................................................................................................. 3.1% 0.6% Catastrophe loss ratio - current year ............................................................................................................................................................................. 0.0% 1.8% Catastrophe loss ratio - prior year development ......................................................................................................................................................... 0.0% 0.8% Loss and loss adjustment expense ratio ...................................................................................................................................................................... 60.3% 52.3% Acquisition cost ratio ........................................................................................................................................................................................................ 21.9% 22.9% Other underwriting expense ratio................................................................................................................................................................................... 9.3% 12.7% Combined ratio ................................................................................................................................................................................................................. 91.5% 87.9% Investments Total assets ....................................................................................................................................................................................................................... $ 7,349,025 $ 6,114,260 Total cash and invested assets(1) ................................................................................................................................................................................... 4,195,642 3,482,726 Total investment return(2) ................................................................................................................................................................................................. $ 147,831 $ 35,982 Two Sigma Hamilton Fund Total net realized and unrealized gains (losses) on investments and net investment income (loss) - TSHF ................................................... $ 262,821 $ 10,064 Net income (loss) attributable to non-controlling interest - TSHF ............................................................................................................................. 120,158 1,510 $ 142,663 $ 8,554 Two Sigma Hamilton Fund return, net of investment management fees and performance incentive allocations ............................................ 8.3% 0.5% 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 ..................................................... $ 5,168 $ 27,428 (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 March 31, ($ in thousands, except per share amounts) 2024 2023 Income (loss) per share attributable to common shareholders - basic ............................................................................................................... $ 1.42 $ 0.50 Income (loss) per share attributable to common shareholders - diluted ............................................................................................................. $ 1.38 $ 0.49 Weighted average common shares outstanding - basic ........................................................................................................................................ 110,921 103,732 Weighted average common shares outstanding - diluted ..................................................................................................................................... 114,246 104,625 Return on average common shareholders' equity - annualized ........................................................................................................................... 29.5% 12.2% At March 31, 2024 At December 31, 2023 Closing common shareholders' equity less intangible assets ............................................................................................................................... $ 2,116,854 $ 1,956,854 Closing common shareholders' equity ...................................................................................................................................................................... $ 2,209,505 $ 2,047,850 Tangible book value per common share ................................................................................................................................................................... $ 19.07 $ 17.75 Book value per common share .................................................................................................................................................................................. $ 19.90 $ 18.58 Year-to-date change in tangible book value per common share .......................................................................................................................... 7.4% 16.0% Year-to-date change in book value per common share ......................................................................................................................................... 7.1% 15.1% Financial Highlights Key Operating and Financial Metrics

6 Three Months Ended March 31, ($ in thousands, except per share amounts) 2024 2023 Revenues Gross premiums written .................................................................................................................................................................................................. $ 721,941 $ 538,164 Reinsurance premiums ceded ....................................................................................................................................................................................... (207,061) (189,666) Net premiums written ....................................................................................................................................................................................................... 514,880 348,498 Net change in unearned premiums ............................................................................................................................................................................... (129,577) (64,596) Net premiums earned ...................................................................................................................................................................................................... 385,303 283,902 Net realized and unrealized gains (losses) on investments ...................................................................................................................................... 255,371 35,133 Net investment income (loss) ......................................................................................................................................................................................... 12,618 2,359 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ................................................................. 267,989 37,492 Third party fee income ..................................................................................................................................................................................................... 7,478 3,004 Other income (loss), excluding third-party fee income ............................................................................................................................................... — 29 Net foreign exchange gains (losses) ............................................................................................................................................................................. (2,125) (2,046) Total revenues ................................................................................................................................................................................................................ 658,645 322,381 Expenses Losses and loss adjustment expenses ......................................................................................................................................................................... 232,352 148,561 Acquisition costs ............................................................................................................................................................................................................... 84,554 65,140 Other underwriting expenses ......................................................................................................................................................................................... 43,353 39,142 Corporate expenses ........................................................................................................................................................................................................ 11,502 6,664 Amortization of intangible assets ................................................................................................................................................................................... 3,252 2,770 Interest expense ............................................................................................................................................................................................................... 5,708 5,529 Total expenses ................................................................................................................................................................................................................ 380,721 267,806 Income (loss) before income tax .................................................................................................................................................................................... 277,924 54,575 Income tax expense (benefit) ......................................................................................................................................................................................... 592 1,573 Net income (loss) ........................................................................................................................................................................................................... 277,332 53,002 Net income (loss) attributable to non-controlling interest ........................................................................................................................................... 120,158 1,510 Net income (loss) and other comprehensive income (loss) attributable to common shareholders ....................................................... $ 157,174 $ 51,492 Per share data Income (loss) per share attributable to common shareholders - basic .................................................................................................................... $ 1.42 $ 0.50 Income (loss) per share attributable to common shareholders - diluted ................................................................................................................. $ 1.38 $ 0.49 Return on average common shareholders' equity - annualized ............................................................................................................................... 29.5% 12.2% Summary Consolidated Results Statements of Operations

7 At March 31, At December 31, At September 30, At June 30, At March 31, ($ in thousands) 2024 2023 2023 2023 2023 Assets Fixed maturity investments, at fair value (amortized cost March 31, 2024: 1,926,329) .......... $ 1,877,130 $ 1,831,268 $ 1,631,471 $ 1,451,249 $ 1,377,937 Short-term investments, at fair value (amortized cost March 31, 2024: 351,035) .................... 352,068 428,878 348,968 336,587 387,826 Investments in Two Sigma Funds, at fair value (cost March 31, 2024: 753,967) ..................... 953,659 851,470 979,986 868,486 656,643 Total investments ................................................................................................................................ 3,182,857 3,111,616 2,960,425 2,656,322 2,422,406 Cash and cash equivalents ............................................................................................................... 1,085,038 794,509 804,548 818,522 945,610 Restricted cash and cash equivalents ............................................................................................. 95,565 106,351 98,979 106,696 139,205 Premiums receivable .......................................................................................................................... 856,111 658,363 689,042 756,275 659,722 Paid losses recoverable ..................................................................................................................... 169,469 145,202 138,314 132,528 72,091 Deferred acquisition costs ................................................................................................................. 190,883 156,895 151,314 145,280 136,094 Unpaid losses and loss adjustment expenses recoverable ......................................................... 1,167,504 1,161,077 1,157,123 1,162,940 1,192,283 Receivables for investments sold ..................................................................................................... 17,777 42,419 19,044 36 33,618 Prepaid reinsurance ............................................................................................................................ 285,984 194,306 232,211 251,818 251,727 Intangible assets ................................................................................................................................. 92,651 90,996 89,589 88,770 87,026 Other assets ......................................................................................................................................... 205,186 209,621 164,015 161,364 174,478 Total assets ........................................................................................................................................ $ 7,349,025 $ 6,671,355 $ 6,504,604 $ 6,280,551 $ 6,114,260 Liabilities, non-controlling interest, and shareholders' equity Liabilities Reserve for losses and loss adjustment expenses ....................................................................... $ 3,148,782 $ 3,030,037 $ 2,948,822 $ 2,899,100 $ 2,891,512 Unearned premiums ........................................................................................................................... 1,132,477 911,222 951,596 924,723 871,333 Reinsurance balances payable ......................................................................................................... 367,123 272,310 367,954 381,678 313,286 Payables for investments purchased ............................................................................................... 55,071 66,606 117,836 18,670 53,889 Term loan, net of issuance costs ...................................................................................................... 149,859 149,830 149,801 149,772 149,744 Accounts payable and accrued expenses ...................................................................................... 155,684 186,887 159,681 149,833 113,832 Payables to related parties ................................................................................................................ 75,797 6,480 9,060 4,497 4,104 Total liabilities .................................................................................................................................... 5,084,793 4,623,372 4,704,750 4,528,273 4,397,700 Non-controlling interest - TS Hamilton Fund ............................................................................ 54,727 133 129 124 120 Shareholders' equity Common shares: Class A, authorized (March 31, 2024: 28,644,807), par value 0.01; issued and outstanding (March 31, 2024: 28,644,807) ........................................................................................................... 286 286 305 305 305 Class B, authorized (March 31, 2024: 72,337,352), par value 0.01; issued and outstanding (March 31, 2024: 56,813,977) ........................................................................................................... 568 560 427 426 427 Class C, authorized (March 31, 2024: 25,544,229), par value 0.01; issued and outstanding (March 31, 2024: 25,544,229) ........................................................................................................... 255 255 305 305 305 Additional paid-in-capital .................................................................................................................... 1,255,055 1,249,817 1,128,553 1,124,566 1,121,334 Accumulated other comprehensive loss.......................................................................................... (4,441) (4,441) (4,441) (4,441) (4,441) Retained earnings ............................................................................................................................... 957,782 801,373 674,576 630,993 598,510 Total shareholders' equity .............................................................................................................. 2,209,505 2,047,850 1,799,725 1,752,154 1,716,440 Total liabilities, non-controlling interest, and shareholders' equity ................................... $ 7,349,025 $ 6,671,355 $ 6,504,604 $ 6,280,551 $ 6,114,260 Summary Consolidated Results Consolidated Balance Sheets

8 At March 31, 2024 ($ in thousands) Consolidated GAAP Balance Sheet Two Sigma Hamilton Fund Balances Unconsolidated Balance Sheet(1) Assets Fixed maturity investments, at fair value ......................................................................................................................................................................... $ 1,877,130 $ - $ 1,877,130 Short-term investments, at fair value ............................................................................................................................................................................... 352,068 (348,155) 3,913 Investments in Two Sigma Funds, at fair value ............................................................................................................................................................. 953,659 911,182 1,864,841 Total investments ................................................................................................................................................................................................................. 3,182,857 563,027 3,745,884 Cash and cash equivalents ................................................................................................................................................................................................ 1,085,038 (706,969) 378,069 Restricted cash and cash equivalents ............................................................................................................................................................................. 95,565 - 95,565 Premiums receivable .......................................................................................................................................................................................................... 856,111 - 856,111 Paid losses recoverable ..................................................................................................................................................................................................... 169,469 - 169,469 Deferred acquisition costs .................................................................................................................................................................................................. 190,883 - 190,883 Unpaid losses and loss adjustment expenses recoverable .......................................................................................................................................... 1,167,504 - 1,167,504 Receivables for investments sold ..................................................................................................................................................................................... 17,777 (13,868) 3,909 Prepaid reinsurance ............................................................................................................................................................................................................ 285,984 - 285,984 Intangible assets .................................................................................................................................................................................................................. 92,651 - 92,651 Other assets ......................................................................................................................................................................................................................... 205,186 (1,024) 204,162 Total assets ......................................................................................................................................................................................................................... $ 7,349,025 $ (158,834) $ 7,190,191 Liabilities, non-controlling interest, and shareholders' equity Liabilities Reserve for losses and loss adjustment expenses ........................................................................................................................................................ $ 3,148,782 $ - $ 3,148,782 Unearned premiums ........................................................................................................................................................................................................... 1,132,477 - 1,132,477 Reinsurance balances payable ......................................................................................................................................................................................... 367,123 - 367,123 Payables for investments purchased ............................................................................................................................................................................... 55,071 (28,132) 26,939 Term loan, net of issuance costs ...................................................................................................................................................................................... 149,859 - 149,859 Accounts payable and accrued expenses ....................................................................................................................................................................... 155,684 (178) 155,506 Payables to related parties ................................................................................................................................................................................................ 75,797 (75,797) - Total liabilities .................................................................................................................................................................................................................... 5,084,793 (104,107) 4,980,686 Non-controlling interest - TS Hamilton Fund ............................................................................................................................................................ 54,727 (54,727) - Shareholders' equity Common shares: Class A, par value $0.01 .................................................................................................................................................................................................... 286 - 286 Class B, par value $0.01 .................................................................................................................................................................................................... 568 - 568 Class C, par value $0.01 .................................................................................................................................................................................................... 255 - 255 Additional paid-in-capital .................................................................................................................................................................................................... 1,255,055 - 1,255,055 Accumulated other comprehensive loss .......................................................................................................................................................................... (4,441) - (4,441) Retained earnings ............................................................................................................................................................................................................... 957,782 - 957,782 Total shareholders' equity .............................................................................................................................................................................................. 2,209,505 - 2,209,505 Total liabilities, non-controlling interest, and shareholders' equity ................................................................................................................... $ 7,349,025 $ (158,834) $ 7,190,191 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 March 31, ($ in thousands) 2024 2023 Net realized gains (losses) on investments ............................................................................................................................................................ $ 149,445 $ (37,651) Fixed maturities and short-term investments ............................................................................................................................................................ (2,942) (5,681) TS Hamilton Fund .......................................................................................................................................................................................................... 152,387 (31,970) Change in net unrealized gains (losses) on investments ................................................................................................................................... 105,926 72,784 Fixed maturities and short-term investments ............................................................................................................................................................ (12,991) 22,557 TS Hamilton Fund .......................................................................................................................................................................................................... 118,917 50,227 Net realized and unrealized gains (losses) on investments ............................................................................................................................... 255,371 35,133 Net investment income (loss): Fixed maturities ................................................................................................................................................................................................................ 16,950 8,155 Short-term investments ................................................................................................................................................................................................... (1) 153 TS Hamilton Fund ............................................................................................................................................................................................................ 3,015 3,888 Cash and cash equivalents ............................................................................................................................................................................................ 4,115 2,309 Other................................................................................................................................................................................................................................... 752 423 Interest and other ........................................................................................................................................................................................................... 24,831 14,928 Management fees ........................................................................................................................................................................................................... (11,950) (12,333) Fixed maturities and short-term investments ............................................................................................................................................................ (591) (394) TS Hamilton Fund .......................................................................................................................................................................................................... (11,359) (11,939) Other expenses ............................................................................................................................................................................................................... (263) (236) Fixed maturities and short-term investments ............................................................................................................................................................ (124) (94) TS Hamilton Fund .......................................................................................................................................................................................................... (139) (142) Net investment income (loss) ..................................................................................................................................................................................... 12,618 2,359 Total net realized and unrealized gains (losses) on investments and net investment income (loss) .................................................... 267,989 37,492 Net income attributable to non-controlling interest ..................................................................................................................................................... 120,158 1,510 Total net realized and unrealized gains (losses) on investments and net investment income (loss), net of non-controlling interest .............................................................................................................................................................................................................................. $ 147,831 $ 35,982 Fixed income, short-term investments and cash and cash equivalents return ...................................................................................................... $ 5,168 $ 27,428 TS Hamilton Fund return(1) .............................................................................................................................................................................................. 142,663 8,554 Summary Consolidated Results Net Investment Return (1) Net of non-controlling interest performance incentive allocation

10 At March 31, 2024 At December 31, 2023 ($ 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 ....................................................................... $ 621,251 28% Aaa $ 708,250 31% Aaa U.S. states, territories and municipalities ................................................ 4,228 —% Aa2 4,370 —% Aa2 Non-U.S. sovereign governments and supranationals ......................... 61,989 3% Aa1 56,246 2% Aa2 Corporate ..................................................................................................... 901,383 41% A2 863,876 39% A3 Residential mortgage-backed securities - Agency ................................. 217,781 10% Aaa 168,513 7% Aaa Residential mortgage-backed securities - Non-agency ........................ 5,422 —% Aaa 4,984 —% Aaa Commercial mortgage-backed securities - Non-agency ....................... 32,470 1% Aaa 10,423 1% Aa1 Other asset-backed securities .................................................................. 32,606 1% Aaa 14,606 1% Aaa Total fixed maturities ................................................................................... 1,877,130 84% Aa3 1,831,268 81% Aa3 Short-term investments ................................................................................ 352,068 16% Aaa 428,878 19% Aaa Total fixed maturities and short-term investments ................................. $ 2,229,198 100% Aa2 $ 2,260,146 100% Aa2 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) At March 31, 2024 At December 31, 2023 Average credit quality ................................................................................... Aa3 Aa3 Average yield to maturity .............................................................................. 4.9% 4.5% Book yield ....................................................................................................... 3.7% 3.6% Expected average duration (in years) ........................................................ 3.3 3.3 (1) Includes $348.2 million and $428.9 million of short-term investments, at March 31, 2024 and December 31, 2023, 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 March 31, 2024 Three Months Ended March 31, 2023 ($ in thousands) International Bermuda Total International Bermuda Total Gross premiums written ......................................................................... $ 320,841 $ 401,100 $ 721,941 $ 247,114 $ 291,050 $ 538,164 Net premiums written .............................................................................. 185,033 329,847 514,880 122,019 226,479 348,498 Net premiums earned ............................................................................. 196,814 188,489 385,303 149,515 134,387 283,902 Third party fee income ............................................................................ 3,586 3,892 7,478 2,902 102 3,004 Losses and loss adjustment expenses ................................................ 116,162 116,190 232,352 70,393 78,168 148,561 Acquisition costs ...................................................................................... 47,720 36,834 84,554 37,193 27,947 65,140 Other underwriting expenses ................................................................ 31,203 12,150 43,353 28,461 10,681 39,142 Underwriting income (loss) .................................................................... $ 5,315 $ 27,207 $ 32,522 $ 16,370 $ 17,693 $ 34,063 Key Ratios: Attritional loss ratio - current year ......................................................... 56.0% 58.4% 57.2% 49.9% 48.1% 49.1% Attritional loss ratio - prior year development ..................................... 2.9% 3.2% 3.1% (4.2%) 6.1% 0.6% Catastrophe loss ratio - current year .................................................... 0.0% 0.0% 0.0% 0.0% 3.9% 1.8% Catastrophe loss ratio - prior year development ................................ 0.1% 0.0% 0.0% 1.4% 0.1% 0.8% Loss and loss adjustment expense ratio ............................................. 59.0% 61.6% 60.3% 47.1% 58.2% 52.3% Acquisition cost ratio ............................................................................... 24.2% 19.5% 21.9% 24.9% 20.8% 22.9% Other underwriting expense ratio ......................................................... 14.0% 4.4% 9.3% 17.1% 7.9% 12.7% Combined ratio ........................................................................................ 97.2% 85.5% 91.5% 89.1% 86.9% 87.9% Segment Results Consolidated Underwriting Results

12 Three Months Ended Year Ended March 31, December 31, September 30, June 30, March 31, December 31, ($ in thousands) 2024 2023 2023 2023 2023 2023 Gross premiums written ......................................................................... $ 721,941 $ 433,791 $ 474,123 $ 504,960 $ 538,164 $ 1,951,038 Net premiums written .............................................................................. 514,880 363,666 383,566 384,708 348,498 1,480,438 Net premiums earned ............................................................................. 385,303 366,135 337,036 331,460 283,902 1,318,533 Third party fee income ............................................................................ 7,478 10,480 2,301 2,449 3,004 18,234 Losses and loss adjustment expenses ................................................ 232,352 195,049 191,577 179,416 148,561 714,603 Acquisition costs ...................................................................................... 84,554 88,615 78,537 76,856 65,140 309,148 Other underwriting expenses ................................................................ 43,353 56,923 44,357 42,743 39,142 183,165 Underwriting income (loss) .................................................................... $ 32,522 $ 36,028 $ 24,866 $ 34,894 $ 34,063 $ 129,851 Key Ratios: Attritional loss ratio - current year ......................................................... 57.2% 53.2% 54.8% 51.0% 49.1% 52.2% Attritional loss ratio - prior year development ..................................... 3.1% (1.7%) (0.1%) (1.6%) 0.6% (0.8%) Catastrophe loss ratio - current year .................................................... 0.0% 1.9% 3.9% 5.0% 1.8% 3.2% Catastrophe loss ratio - prior year development ................................ 0.0% (0.1%) (1.8%) (0.3%) 0.8% (0.4%) Loss and loss adjustment expense ratio ............................................. 60.3% 53.3% 56.8% 54.1% 52.3% 54.2% Acquisition cost ratio ............................................................................... 21.9% 24.2% 23.3% 23.2% 22.9% 23.4% Other underwriting expense ratio .......................................................... 9.3% 12.7% 12.5% 12.2% 12.7% 12.5% Combined ratio ........................................................................................ 91.5% 90.2% 92.6% 89.5% 87.9% 90.1% Segment Results 5Q Consolidated Underwriting Results - Group

13 Three Months Ended Year Ended March 31, December 31, September 30, June 30, March 31, December 31, ($ in thousands) 2024 2023 2023 2023 2023 2023 Gross premiums written ......................................................................... $ 320,841 $ 273,472 $ 307,140 $ 277,796 $ 247,114 $ 1,105,522 Net premiums written .............................................................................. 185,033 216,712 234,621 197,047 122,019 770,399 Net premiums earned ............................................................................. 196,814 198,725 178,632 176,636 149,515 703,508 Third party fee income ............................................................................ 3,586 2,267 2,115 2,401 2,902 9,685 Losses and loss adjustment expenses ................................................ 116,162 106,349 97,820 87,575 70,393 362,137 Acquisition costs ...................................................................................... 47,720 55,009 47,236 47,260 37,193 186,698 Other underwriting expenses ................................................................ 31,203 37,767 31,634 29,540 28,461 127,402 Underwriting income (loss) .................................................................... $ 5,315 $ 1,867 $ 4,057 $ 14,662 $ 16,370 $ 36,956 Key Ratios: Attritional loss ratio - current year ......................................................... 56.0% 54.5% 54.6% 52.9% 49.9% 53.2% Attritional loss ratio - prior year development ..................................... 2.9% (1.4%) (5.3%) (3.3%) (4.2%) (3.5%) Catastrophe loss ratio - current year .................................................... 0.0% 0.0% 5.1% 0.9% 0.0% 1.5% Catastrophe loss ratio - prior year development ................................ 0.1% 0.4% 0.4% (0.9%) 1.4% 0.3% Loss and loss adjustment expense ratio ............................................. 59.0% 53.5% 54.8% 49.6% 47.1% 51.5% Acquisition cost ratio ............................................................................... 24.2% 27.7% 26.4% 26.8% 24.9% 26.5% Other underwriting expense ratio .......................................................... 14.0% 17.9% 16.5% 15.4% 17.1% 16.7% Combined ratio ........................................................................................ 97.2% 99.1% 97.7% 91.8% 89.1% 94.7% Segment Results 5Q Underwriting Results - International

14 Three Months Ended Year Ended March 31, December 31, September 30, June 30, March 31, December 31, ($ in thousands) 2024 2023 2023 2023 2023 2023 Gross premiums written ......................................................................... $ 401,100 $ 160,319 $ 166,983 $ 227,164 $ 291,050 $ 845,516 Net premiums written .............................................................................. 329,847 146,954 148,945 187,661 226,479 710,039 Net premiums earned ............................................................................. 188,489 167,410 158,404 154,824 134,387 615,025 Third party fee income ............................................................................ 3,892 8,213 186 48 102 8,549 Losses and loss adjustment expenses ................................................ 116,190 88,700 93,757 91,841 78,168 352,466 Acquisition costs ...................................................................................... 36,834 33,606 31,301 29,596 27,947 122,450 Other underwriting expenses ................................................................ 12,150 19,156 12,723 13,203 10,681 55,763 Underwriting income (loss) .................................................................... $ 27,207 $ 34,161 $ 20,809 $ 20,232 $ 17,693 $ 92,895 Key Ratios: Attritional loss ratio - current year ......................................................... 58.4% 51.8% 55.1% 48.9% 48.1% 51.1% Attritional loss ratio - prior year development ..................................... 3.2% (2.2%) 5.7% 0.3% 6.1% 2.3% Catastrophe loss ratio - current year .................................................... 0.0% 4.1% 2.6% 9.8% 3.9% 5.1% Catastrophe loss ratio - prior year development ................................ 0.0% (0.7%) (4.2%) 0.3% 0.1% (1.2%) Loss and loss adjustment expense ratio ............................................. 61.6% 53.0% 59.2% 59.3% 58.2% 57.3% Acquisition cost ratio ............................................................................... 19.5% 20.1% 19.8% 19.1% 20.8% 19.9% Other underwriting expense ratio .......................................................... 4.4% 6.5% 7.9% 8.5% 7.9% 7.7% Combined ratio ........................................................................................ 85.5% 79.6% 86.9% 86.9% 86.9% 84.9% Segment Results 5Q Underwriting Results - Bermuda

15 Region Peril Probability of Exceedance Group Net PML ($m)(1) % of Shareholders' Equity Florida U.S. Hurricane 1 in 100 $ 194.0 8.8% Northeast U.S. Hurricane 1 in 100 176.1 8.0% Gulf (TX - AL) U.S. Hurricane 1 in 100 164.4 7.4% California Earthquake 1 in 250 273.1 12.4% Pacific Northwest Earthquake 1 in 250 109.5 5.0% (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 April 1, 2024 ($ in millions)

16 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 are considered non-GAAP financial measures under SEC rules and regulations. In this Supplementary Financial Information, we present underwriting income (loss), a non-GAAP financial measure as defined in Item 10(e) of SEC Regulation S-K. We believe that 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 comparable GAAP figures 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 following table reconciles underwriting income (loss) to net income (loss), the most comparable GAAP financial measure: Three Months Ended March 31, ($ in thousands) 2024 2023 Underwriting income (loss) ............................................................................................................................................................................................ $ 32,522 $ 34,063 Total net realized and unrealized gains (losses) on investments and net investment income (loss) ................................................................ 267,989 37,492 Other income (loss), excluding third party fee income .............................................................................................................................................. — 29 Net foreign exchange gains (losses) ............................................................................................................................................................................ (2,125) (2,046) Corporate expenses ....................................................................................................................................................................................................... (11,502) (6,664) Amortization of intangible assets .................................................................................................................................................................................. (3,252) (2,770) Interest expense .............................................................................................................................................................................................................. (5,708) (5,529) Income tax (expense) benefit ........................................................................................................................................................................................ (592) (1,573) Net income (loss), prior to non-controlling interest .................................................................................................................................................... $ 277,332 $ 53,002 Three Months Ended March 31, ($ in thousands) 2024 2023 Third party fee income .................................................................................................................................................................................................... $ 7,478 $ 3,004 Other income (loss), excluding third party fee income .............................................................................................................................................. — 29 Other income (loss) ........................................................................................................................................................................................................ $ 7,478 $ 3,033 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 fees earned by the International Segment for management services provided to third party syndicates and consortia and by the Bermuda Segment for performance based management fees generated by our third party capital manager, Ada Capital Management Limited. We believe that this measure is a relevant component of our underwriting income (loss).

17 Three Months Ended March 31, ($ in thousands) 2024 2023 Other underwriting expenses ........................................................................................................................................................................................ $ 43,353 $ 39,142 Corporate expenses ....................................................................................................................................................................................................... 11,502 6,664 General and administrative expenses ......................................................................................................................................................................... $ 54,855 $ 45,806 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 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 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. 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. 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 Hamilton Insurance Group, Ltd. March 31, 2024

2 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,” 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 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, 2023 (the “Form 10-K”) and other subsequent periodic reports filed with the Securities and Exchange Commission and the following: • our results of operations and financial condition could be adversely affected by unpredictable catastrophic events, global climate change or emerging claim and coverage issues; • our business could be materially adversely affected if we do not accurately assess our underwriting risk, our reserves are inadequate to cover our actual losses, our models or assessments and pricing of risks are incorrect or we lose important broker relationships; • the insurance and reinsurance business is historically cyclical and the pricing and terms for our products may decline, which would affect our profitability and ability to maintain or grow premiums; • we have significant foreign operations that expose us to certain additional risks, including foreign currency risks and political risk; • we do not control the allocations to and/or the performance of the Two Sigma Hamilton Fund, LLC ("TS Hamilton Fund")’s investment portfolio, and its performance depends on the ability of its investment manager, Two Sigma Investments, LP (“Two Sigma”), to select and manage appropriate investments and we have a limited ability to withdraw our capital accounts; • Two Sigma Principals, LLC, Two Sigma and their respective affiliates have potential conflicts of interest that could adversely affect us; • the historical performance of Two Sigma is not necessarily indicative of the future results of the TS Hamilton Fund’s investment portfolio or of our future results • our ability to manage risks associated with macroeconomic conditions resulting from geopolitical and global economic events, including public health crises, current or anticipated military conflicts, terrorism, sanctions, rising energy prices, inflation and interest rates and other global events; • our ability to compete successfully with more established competitors and risks relating to consolidation in the reinsurance and insurance industries; • downgrades, potential downgrades or other negative actions by rating agencies; • our dependence on key executives, including the potential loss of Bermudian personnel as a result of Bermuda employment restrictions, and the inability to attract qualified personnel, particularly in very competitive hiring conditions; • our dependence on letter of credit facilities that may not be available on commercially acceptable terms; • our potential need for additional capital in the future and the potential unavailability of such capital to us on favorable terms or at all;

3 • the suspension or revocation of our subsidiaries’ insurance licenses; • risks associated with our investment strategy, including such risks being greater than those faced by competitors; • changes in the regulatory environment and the potential for greater regulatory scrutiny of the Company going forward; • a cyclical downturn of the reinsurance industry; • operational failures, failure of information systems or failure to protect the confidentiality of customer information, including by service providers, or losses due to defaults, errors or omissions by third parties or our affiliates; • we are a holding company with no direct operations, and our insurance and reinsurance subsidiaries’ ability to pay dividends and other distributions to us is restricted by law; • risks relating to our ability to identify and execute opportunities for growth or our ability to complete transactions as planned or realize the anticipated benefits of our acquisitions or other investments; • our potentially becoming subject to U.S. federal income taxation, Bermuda taxation or other taxes as a result of a change of tax laws or otherwise; • the potential characterization of us and/or any of our subsidiaries as a passive foreign investment company, or PFIC; • our potentially becoming subject to U.S. withholding and information reporting requirements under the U.S. Foreign Account Tax Compliance Act, or FATCA, provisions; • our costs will increase as a result of operating as a public company, and our management will be required to devote substantial time to complying with public company regulations; • if we were to identify a material weakness and were unable to remediate such material weakness, or fail to achieve and maintain effective internal controls, our operating results and financial condition could be impacted and the market price of our Class B common shares may be negatively affected; • the lack of a prior public market for our Class B common shares means our share price may be volatile and anti-takeover provisions contained in our organizational documents could delay management changes; • the potential that the market price of our Class B common shares could decline due to future sales of shares by our existing shareholders; • applicable insurance laws, which could make it difficult to effect a change of control of our company; and • investors may have difficulties in serving process or enforcing judgments against us in the United States. There may be other factors that could cause our actual results to differ materially from the forward-looking statements, including factors disclosed under the sections entitled “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” in the Form 10-K and other subsequent periodic reports filed with the Securities and Exchange Commission. 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. Special Note Regarding Forward-Looking Statements, continued

Introduction to Hamilton

5 Highly Entrepreneurial & Experienced Leadership Team Fostering an Attractive Culture Gemma Carreiro 20+ Years General Counsel Former: PartnerRe Pina Albo 30+ Years Group CEO Former: Munich Re Megan Thomas 20+ Years CEO, Hamilton Re Former: AIG Venkat Krishnamoorthy 30+ Years (IT Industry) Group CTO Former: Coleman Research Group Craig Howie 35+ Years Group CFO Former: Everest Anita Kuchma 35+ Years CEO, Hamilton Select Former: Munich Re Alex Baker 20+ Years Group Chief Risk Officer Former: Chubb Insurance Adrian Daws 20+ Years CEO, Hamilton Global Specialty Former: CNA Hardy Daniel Fisher 20+ Years Group Head of HR, Communications & Culture Former: Munich Re Executive Leadership In Good Company Management team with 230+ years of collective (re)insurance experience Highly Collaborative Service Oriented Open, Diverse and Inclusive Expertise Experienced Board of Directors

6 Hamilton – Overview and Results Annual Segmental Results Group Financial Highlights $4.2B Q1 2024 Cash & Invested Assets $2.2B Q1 2024 Shareholders’ Equity 550+ Employees “A” (Stable) AM Best Financial Strength Rating* $2.0B FY 2023 $722m 1Q 2024 Gross Premiums Written $130m FY 2023 $33m 1Q 2024 Underwriting Income 90.1% FY 2023 91.5% 1Q 2024 Combined Ratio $259m FY 2023 $157m 1Q 2024 Net Income R e p o rt in g S e g m e n ts International 2023 GPW $1.1B Bermuda 2023 GPW $846m 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 23 S e g m e n t C o m b in e d R at io 94.7% 84.9% *Ratings of Hamilton Re, Ltd. and Hamilton Insurance DAC.

7 ▪ Lloyd’s Syndicate 4000 ▪ Hamilton Insurance DAC (Ireland) ▪ HMGA Americas (In House US MGA) ▪ 90+ underwriters Insurance 57% Reinsurance 43% Insurance / Reinsurance GPW: $2.0B1 Casualty 46% Specialty 31% Property 23% Class of Business GPW: $2.0B1 International 57% Bermuda 43% Business Segments GPW: $2.0B1 Efficient Global Footprint A Scaled Global Operation – Managing Across Market Cycles Our 2023 business was diversified by (re)insurance, main classes of business, and segment Two Business Segments and Three Underwriting Platforms Hamilton Global Specialty Hamilton Select Hamilton Re ▪ Hamilton Select ▪ 40+ underwriters ▪ Hamilton Re ▪ Hamilton Re US ▪ 25+ underwriters International Bermuda Three complementary underwriting platforms to maximize returns through the cycle 1. Gross premiums written figures for the year ended December 31, 2023.

8 Hamilton is Guided by Four Business Imperatives • Data driven, disciplined underwriting & risk-management culture • Effectively managing volatility from natural catastrophe events Sustainable Underwriting Profitability • Three complementary underwriting platforms with expertise in cycle management • Double digit growth every year since 2018 reflecting cycle dynamicsStrategic Growth • Combination of proprietary and partner technology solutions • Enable data informed decisions, operational efficiency and digital automationTechnology Enablement • Attracting and retaining top talent in a highly competitive marketplace • Collaborative culture with high accountability and ownership mentalityMagnet for Talent You’re “In good company” with Hamilton 1 2 3 4

9 85% 71% 68% 60% 54% 52% 60% 41% 40% 38% 37% 36% 36% 31% 126% 111% 106% 96% 90% 88% 92% 2019 2020 2021 2022 2023 Q1 2023 Q1 2024 $731 $1,087 $1,447 $1,647 $1,951 $538 $722 2019 2020 2021 2022 2023 Q1 2023 Q1 2024 Hamilton Group – Strategic Growth and Sustainable Underwriting Profitability Hamilton Group - Gross Premiums Written ($’m) Hamilton Group - Combined Ratio (1) Loss Ratio Expense Ratio (2) 1) Numbers may not add due to rounding. 2) Excludes impact of Ukraine Conflict; Combined ratio including the Ukraine Conflict was 103%. Double digit top line growth with bottom line improvement

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 12% 45% 43% Property Casualty Specialty 2023 GPW Business Mix 90% 10% Insurance Reinsurance $1.1B Leading specialty insurance business with a track record of profitability and low volatility Specialized underwriters leading consortia on behalf of other brand name peers Ability to offer both Lloyd’s and company paper across multiple platforms Longstanding client & broker relationships fuel growth in core E&S markets Limited legacy exposures Hamilton Select: New US domiciled carrier writing SME hard-to-place E&S business Hamilton Select $78m / 7%

12 103% 65% 63% 50% 52% 47% 59% 50% 46% 44% 43% 43% 42% 38% 153% 111% 108% 93% 95% 89% 97% 2019 2020 2021 2022 2023 Q1 2023 Q1 2024(2) Hamilton made transformative acquisition of Pembroke Managing Agency in 2019 International Segment: Measured Growth Following Significant Acquisition in 2019 $277 $662 $892 $933 $1,106 $247 $321 2019 2020 2021 2022 2023 Q1 2023 Q1 2024 International Segment - Gross Premiums Written ($’m) International Segment - Combined Ratio (1) Loss Ratio Expense Ratio 1) Numbers may not add due to rounding. 2) Excludes impact of Ukraine Conflict; Combined ratio including the Ukraine Conflict was 103%.

13 Growing, scalable and diversified platform Underwriting profitability through portfolio optimization and cycle management Accelerate targeted growth in current favorable reinsurance market, complementing cat offerings with other lines of business Ability to write reinsurance business through both Bermuda and US underwriting teams Clear, consistent appetite and responsive service rewarded by clients and brokers Data-driven, digital approach supports underwriting and operational efficiencies Bermuda Segment: Well Diversified Writer of Property, Casualty and Specialty Classes Underwriting-focused operation with strong foundation to capture growth opportunities 38% 47% 15% Property Casualty Specialty 14% 86% Insurance Reinsurance 2023 GPW Business Mix $846m

14 Current portfolio mix has resulted in meaningful growth and improved underwriting results Bermuda Segment: Strategic Growth Following Portfolio Optimization 74% 81% 75% 72% 57% 58% 62% 36% 31% 29% 29% 28% 29% 24% 110% 111% 104% 101% 85% 87% 86% 2019 2020 2021 2022 2023 Q1 2023 Q1 2024 $454 $425 $554 $713 $846 $291 $401 2019 2020 2021 2022 2023 Q1 2023 Q1 2024 Bermuda Segment - Gross Premiums Written ($’m) Bermuda Segment - Combined Ratio (1) Loss Ratio Expense Ratio (2) 1) Numbers may not add due to rounding. 2) Excludes impact of Ukraine Conflict; Combined ratio including the Ukraine Conflict was 103%.

Invested Assets

16 Focused on delivering a combination of stable investment income and low-correlated absolute returns Hamilton Invested Assets $4.2 billion in invested assets at March 31, 2024 Two distinct investment portfolios: fixed income and total return Fixed income portfolio focuses on preservation of capital and high liquidity Total return portfolio provides uncorrelated returns with moderate volatility and high liquidity – TSHF return of 8.3% for Q1 2024 Portfolio mix of 56% fixed income and short-term / 44% total return at March 31, 2024

17 Two Sigma Hamilton FundFixed Income PortfolioA B Preservation of Capital 1 Liquidity 2 Diversification 3 Attractive Returns 4 Risk Management & Governance 5 ✓ Aa3 average credit quality 100% investment grade ✓ Highly liquid ✓ Market sector diversification ✓ 3.7% book yield, 1Q24 ✓ Investment guidelines from Investment Committee ✓ Low-correlation to equity markets; long- term positive returns ✓ Redeemable within 5 days ✓ 3 unique investment vehicles ✓ 12.9% annualized return since inception (2014) ✓ Hold lesser of $1.8B or 60% of Hamilton net tangible assets in TSHF; arms- length IMA with Two Sigma Review of Investment Strategy - $4.2 Billion Investment Portfolio Fixed Income and Short-Term 56% / $2.3B Two Sigma Hamilton Fund 44% / $1.9B

18 Fixed Income Investment Portfolio as of March 31, 2024 48% 33% 12% 7% Corporate US Treasury US Agency Other $1.9B Corporate A2 US Treas. Aaa US Agency Aaa Other Aa1 Fixed Income portfolio is managed by two external managers Fixed income investments of $1.9 billion – Average rating of Aa3, and duration of 3.3 years

19 Overview of Two Sigma and TSHF Diversified fund focused on liquid strategies in global equities, fixed income, futures, and FX markets ▪ Two Sigma Investment Management aims to deliver low-correlated absolute returns through the systematic application of fundamental, technical, alpha capture and event models ▪ Manages over $63B 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 2,000 employees of which ~1,000 are research and development professionals ▪ 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 fixed income, global equities, futures and FX markets Two Sigma Hamilton Fund $1.9B TSHF as of March 31, 2024 12.9% Average annualized returns 2014-1Q24 Dedicated- fund of one 3 portfolios 2 equity focused, 1 macro focused Highly liquid Investments TSHF Annual Returns Since 2018 Two Sigma Hamilton Fund, LLC (“TSHF”) 1.40 Sharpe Ratio since inception 19.9% 6.1% -4.6% 17.7% 4.6% 7.6% 2018 2019 2020 2021 2022 2023 1) TSHF Annual Returns correspond to Hamilton Fiscal Year which was Dec 1- Nov 30 until FY 2022.

Investing in Hamilton

21 5 A scaled, diversified, global specialty insurance and reinsurance operation Highly entrepreneurial & experienced leadership team fostering a distinctive and attractive culture Disciplined and data-driven underwriting approach to drive sustainable profitability Strong balance sheet with significant financial flexibility Proprietary technology infrastructure to support underwriting and operational efficiencies Differentiated asset management capabilities with Two Sigma to enhance investment returns Ability to grow profitably, navigating across all market cycles Poised to Deliver Significant Shareholder Value Hamilton Insurance Group - Who We Are Today

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

Cover	May 08, 2024
Cover [Abstract]
Document Type	8-K
Document Period End Date	May 08, 2024
Entity Registrant Name	Hamilton Insurance Group, Ltd.
Entity Incorporation, State or Country Code	D0
Entity File Number	001-41862
Entity Tax Identification Number	98-1153847
Entity Address, Address Line One	Wellesley House North, 1st Floor
Entity Address, Address Line Two	90 Pitts Bay Road
Entity Address, City or Town	Pembroke
Entity Address, Country	BM
Entity Address, Postal Zip Code	HM 08
City Area Code	441
Local Phone Number	405-5200
Written Communications	false
Soliciting Material	false
Pre-commencement Tender Offer	false
Pre-commencement Issuer Tender Offer	false
Title of 12(b) Security	Class B common shares, par value $0.01 per share
Trading Symbol	HG
Security Exchange Name	NYSE
Entity Emerging Growth Company	false
Amendment Flag	false
Entity Central Index Key	0001593275

Hamilton Insurance (NYSE:HG)
Historical Stock Chart
From Apr 2024 to May 2024

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Hamilton Insurance (NYSE:HG)
Historical Stock Chart
From May 2023 to May 2024

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