8-K - BOW - Equibles

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

Date of Report (Date of earliest event reported): February 24, 2026

Bowhead Specialty Holdings Inc.

(Exact name of registrant as specified in its charter)

Delaware	001-42111	87-1433334
(State or other jurisdiction<br><br>of incorporation)	(Commission File Number)	(IRS Employer Identification No.)
	452 Fifth Avenue<br><br>New York, New York 10018
	(Address of principal executive offices)
	(212) 970-0269
	(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:

£ Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

£ Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

£ Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

£ 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(s)	Name of each exchange on which registered
Common Stock, par value $0.01 per share	BOW	New York Stock Exchange

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 under the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 under the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).

Emerging growth company T

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. £

Item 2.02 Results of Operations and Financial Condition.

On February 24, 2026, Bowhead Specialty Holdings Inc. (the "Company") issued a press release announcing its financial results for the three months and twelve months ended December 31, 2025. A copy of the press release is furnished as Exhibit 99.1 to this Current Report on Form 8-K.

Item 7.01 Regulation FD Disclosure.

On February 24, 2026, the Company made available to investors an investor presentation for the period ended December 31, 2025 (the "Investor Presentation"). The Investor Presentation is furnished as Exhibit 99.2 hereto. The Investor Presentation is also available on the Investors section of the Company's website, free of charge, at https://ir.bowheadspecialty.com.

Item 9.01. Financial Statements and Exhibits.

(d) Exhibits.

Exhibit No.	Description
99.1	Press Release of the Company, dated February 24, 2026
99.2	Bowhead Specialty Holdings Inc. Investor Presentation for the period ended December 3 1 , 2025
104	Cover Page Interactive Data File - the cover page XBRL tags are embedded within the Inline XBRL document

SIGNATURES

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

Dated: February 24, 2026

By:	/s/Brad Mulcahey
Name:	Brad Mulcahey
Title:	Chief Financial Officer and Treasurer

Document

Bowhead Specialty Holdings Inc. Reports Fourth Quarter and Full Year 2025 Results

NEW YORK, New York. (BusinessWire) – February 24, 2026 – Bowhead Specialty Holdings Inc. (NYSE: BOW), a specialty lines insurance group focused on providing casualty, professional liability and healthcare liability insurance products, delivered through complementary “craft” and “digital” underwriting models, today announced financial results for the fourth quarter and year ended December 31, 2025(1).

Fourth Quarter 2025 Highlights

•Gross written premiums increased 21.3% to $224.1 million.

•Net income of $14.8 million, or $0.44 per diluted share.

•Adjusted net income(2) of $15.5 million, or $0.47 per diluted share(2).

•Return on equity of 13.5% and adjusted return on equity(2) of 14.1%.

•Book value per share $13.70 and diluted book value per share of $13.45.

Full Year 2025 Highlights

•Gross written premiums increased 24.0% to $862.8 million.

•Net income of $53.8 million, or $1.59 per diluted share.

•Adjusted net income(2) of $55.6 million, or $1.65 per diluted share(2).

•Return on equity of 13.1% and adjusted return on equity(2) of 13.6%.

Bowhead Chief Executive Officer, Stephen Sills, commented, “Bowhead had a great year in 2025. Gross written premiums grew more than 21% in the fourth quarter, and 24% for the full year. At the start of the year, we expected a low 30s expense ratio for the full year of 2025 but achieved an expense ratio below 30% starting in the third quarter and for the full year of 2025. With these accomplishments, Bowhead’s adjusted net income for the year grew over 30%, adjusted return on equity was 13.6%, and diluted adjusted earnings per share was $1.65.”

“With a strong year behind us, I’m even more excited about Bowhead’s future. Over the past five years, we’ve built a highly effective “craft” underwriting model driven by experienced underwriters who excel at writing large and complex risks. In the second half of 2024, we supplemented this foundation by launching our complementary “digital” underwriting model, starting with Baleen, targeting small, harder-to-place risks with more restrictive coverage. In Baleen’s first full year, we generated over $21 million in premiums — an important milestone that validates our digital strategy. Since then, we’ve leveraged technology to streamline the submission, underwriting, and servicing of our existing Bowhead products, a capability we call “express”, to address small and mid-sized accounts, beginning with our small cyber liability products.”

“While we continue to expect a GWP growth of around 20% in 2026 driven by our Casualty division, our digital expansion marks a major step forward for Bowhead, positioning us well to deliver sustainable and profitable growth across market cycles.”

Underwriting Results

The 21.3% increase in gross written premiums to $224.1 million in the fourth quarter of 2025 was driven by our increasing renewal book, new business and the continued growth in our platform across all divisions:

•Our Casualty division led the growth with a 25.5% increase to $132.9 million;

•Professional Liability increased 4.2% to $47.9 million;

•Healthcare Liability increased 7.7% to $34.2 million; and

•Baleen Specialty increased 665.6% to $9.1 million.

Due to the timing of our independent actuarial review in fourth quarter of each year, we consider our full-year loss ratio a more meaningful metric. Our loss ratio for the year of 66.7% increased 2.3 points compared to 64.4% in 2024.

Our current accident year loss ratio increased 1.8 points due in part to higher expected loss ratios on certain reserves within Professional Liability and Healthcare Liability to align more closely with industry expected loss ratios and our own limited loss experience. The increase was also due to mix changes in our portfolio, where Casualty, which had comparatively higher expected loss ratios, comprised a larger proportion of our net earned premiums compared to the prior year.

Similar to previous quarters in 2025, the 0.5 point increase in our prior accident year loss ratio was due to expected loss ratios applied to audit premiums fully earned in the year, but associated with prior accident years. This increase was not based on actual losses settling for more than reserved, and did not represent an increase in estimated reserves on unresolved claims. We are simply putting loss reserves into the appropriate accident year regardless of when the premiums are billed and earned. As part of our annual independent actuarial reserve review, we also reallocated prior accident year loss reserves between accident years and by division, primarily from Casualty to Professional Liability, resulting in no prior accident year development on an aggregate basis.

Due to Bowhead’s limited loss experience, we continue to hold expected loss ratios that rely on development patterns and other inputs primarily based on industry data.

Our expense ratio decreased 1.0 point to 29.1% in the fourth quarter of 2025 and 1.6 points to 29.8% in for the year ended December 31, 2025. The full year decrease from 31.4% in 2024 was primarily driven by a reduction in our operating expense ratio, which was partially offset by the increase in our net acquisition ratio. The decrease in our operating expenses ratio was due to the continued scaling of our business, where net earned premiums grew at a higher rate than our expenses, as well as the prudent management of our expenses. The increase in our net acquisition costs ratio was driven by the increase in earned broker commissions due to changes in our portfolio mix and, to a lesser extent, the increase in the ceding fee we pay to American Family.

Investment Results

Net investment income increased 35.8% in the fourth quarter of 2025 to $16.6 million and 44.1% to $57.8 million for the year ended December 31, 2025, driven by a higher balance of investments and, to a lesser extent, higher yields on invested assets. Our investment portfolio, which included cash equivalents, had a book yield of 4.6% and a new money rate of 4.5% at the end of the year.

The weighted average effective duration of our investment portfolio, which included cash equivalents, was 3.0 years and had an average rating of “AA” at December 31, 2025.

__________________

(1)Comparisons in this release are made to December 31, 2024 financial results unless otherwise noted.

(2)Non-GAAP financial measure. See “Reconciliation of Non-GAAP Financial Measures” for a reconciliation of the non-GAAP financial measures to their most directly comparable U.S. GAAP measures.

Summary of Operating Results

The following table summarizes the Company’s results of operations for the three and twelve months ended December 31, 2025 and 2024:

	Three Months Ended December 31,							Twelve Months Ended December 31,
	2025		2024			% Change		2025			2024			% Change
	( in thousands, except percentages and per share data)
Gross written premiums			$	184,769		21.3	%	$	862,806		$	695,717		24.0	%
Ceded written premiums	(80,540)		(64,585)			24.7	%	(304,619)			(244,295)			24.7	%
Net written premiums			$	120,184		19.4	%	$	558,187		$	451,422		23.7	%
Revenues
Net earned premiums			$	106,864		25.7	%	$	491,677		$	385,111		27.7	%
Net investment income	16,553		12,193			35.8	%	57,827			40,121			44.1	%
Net realized investment gains (losses)	73		—			NM		43			(16)			368.8	%
Other insurance-related income	735		274			168.2	%	2,042			444			359.9	%
Total revenues	151,678		119,331			27.1	%	551,589			425,660			29.6	%
Expenses
Net losses and loss adjustment expenses	91,087		66,937			36.1	%	328,022			248,099			32.2	%
Net acquisition costs	13,166		9,130			44.2	%	46,513			32,397			43.6	%
Operating expenses	26,640		23,352			14.1	%	102,264			89,112			14.8	%
Non-operating expenses	95		622			(84.7)	%	1,425			2,807			(49.2)	%
Warrant expense	792		792			NM		3,142			1,917			63.9	%
Interest expense and financing fees	1,243		248			401.2	%	2,012			725			177.5	%
Loss on extinguishment of credit facility	862		—			NM		862			—			NM
Foreign exchange (gains) losses	(14)		1			NM		50			68			(26.5)	%
Total expenses	133,871		101,082			32.4	%	484,290			375,125			29.1	%
Income before income taxes	17,807		18,249			(2.4)	%	67,299			50,535			33.2	%
Income tax expense	(2,963)		(4,642)			(36.2)	%	(13,513)			(12,292)			9.9	%
Net income			$	13,607		9.1	%	$	53,786		$	38,243		40.6	%
Key Operating and Financial Metrics:
Adjusted net income(1)			$	14,099		10.2	%	$	55,598		$	42,686		30.2	%
Loss ratio	67.8	%	62.6		%			66.7		%	64.4		%
Expense ratio	29.1	%	30.1		%			29.8		%	31.4		%
Combined ratio	96.9	%	92.7		%			96.5		%	95.8		%
Return on equity(2)	13.5	%	14.8		%			13.1		%	13.6		%
Adjusted return on equity(1)(2)	14.1	%	15.3		%			13.6		%	15.2		%
Diluted earnings per share			$	0.41		7.3	%	$	1.59		$	1.29		23.3	%
Diluted adjusted earnings per share(1)			$	0.42		11.9	%	$	1.65		$	1.44		14.6	%

All values are in US Dollars.

__________________

NM - Percentage change is not meaningful.

(1)Non-GAAP financial measure. See “Reconciliation of Non-GAAP Financial Measures” for a reconciliation of the non-GAAP financial measures to their most directly comparable U.S. GAAP measures.

(2)For the three months ended December 31, 2025 and 2024, net income and adjusted net income are annualized to arrive at return on equity and adjusted return on equity.

Condensed Consolidated Balance Sheets

	December 31,<br>2024

Assets
Investments
Fixed maturity securities, available for sale, at fair value (amortized cost of 1,364,228 and 894,145, respectively)	$	879,989
Short-term investments, at amortized cost, which approximates fair value	9,997
Total investments	889,986
Cash and cash equivalents	97,476
Restricted cash and cash equivalents	124,582
Accrued investment income	7,520
Premium balances receivable	63,672
Reinsurance recoverable, net	255,072
Prepaid reinsurance premiums	152,567
Deferred policy acquisition costs	27,625
Property and equipment, net	6,845
Income taxes receivable	586
Deferred tax assets, net	20,340
Other assets	7,971
Total assets	$	1,654,242
Liabilities
Reserve for losses and loss adjustment expenses	$	756,859
Unearned premiums	446,850
Reinsurance balances payable	51,856
Debt	—
Income taxes payable	1,571
Accrued expenses	18,010
Other liabilities	8,654
Total liabilities	1,283,800
Commitments and contingencies (Note 14)
Mezzanine equity
Performance stock units	265
Stockholders' equity
Common stock	327
(0.01 par value; 400,000,000 shares authorized, 32,783,451 and 32,662,683 shares issued and outstanding at December 31, 2025 and December 31, 2024, respectively)
Additional paid-in capital	318,095
Accumulated other comprehensive income (loss)	(11,154)
Retained earnings	62,909
Total stockholders' equity	370,177
Total mezzanine equity and stockholders' equity	370,442
Total liabilities, mezzanine equity and stockholders' equity	$	1,654,242

All values are in US Dollars.

Gross Written Premiums

The following tables present gross written premiums by underwriting division for the three and twelve months ended December 31, 2025 and 2024:

	Three Months Ended December 31,
	2025	% of Total		2024		% of Total		Change	% Change
	( in thousands, except percentages)
Casualty		59.3	%	$	105,872	57.3	%		25.5	%
Professional Liability	47,928	21.4	%	46,010		24.9	%	1,918	4.2	%
Healthcare Liability	34,153	15.2	%	31,699		17.2	%	2,454	7.7	%
Baleen Specialty	9,095	4.1	%	1,188		0.6	%	7,907	665.6	%
Gross written premiums		100.0	%	$	184,769	100.0	%		21.3	%

All values are in US Dollars.

	Twelve Months Ended December 31,
	2025	% of Total		2024		% of Total		Change	% Change
	( in thousands, except percentages)
Casualty		63.8	%	$	431,817	62.1	%		27.5	%
Professional Liability	174,419	20.2	%	160,651		23.1	%	13,768	8.6	%
Healthcare Liability	116,290	13.5	%	101,619		14.6	%	14,671	14.4	%
Baleen Specialty	21,431	2.5	%	1,630		0.2	%	19,801	1214.8	%
Gross written premiums		100.0	%	$	695,717	100.0	%		24.0	%

All values are in US Dollars.

The following tables present gross written premiums by underwriting model(1) for the three and twelve months ended December 31, 2025 and 2024:

	Three Months Ended December 31,
	2025	% of Total		2024		% of Total		Change	% Change
	( in thousands, except percentages)
Craft		95.2	%	$	183,581	99.4	%		16.2	%
Digital
Baleen Specialty	9,095	4.1	%	1,188		0.6	%	7,907	665.6	%
Express	1,673	0.7	%	—		—	%	1,673	NM
Digital	10,768	4.8	%	1,188		0.6	%	9,580	806.4	%
Gross written premiums		100.0	%	$	184,769	100.0	%		21.3	%

All values are in US Dollars.

	Twelve Months Ended December 31,
	2025	% of Total		2024		% of Total		Change	% Change
	( in thousands, except percentages)
Craft		97.2	%	$	694,087	99.8	%		20.9	%
Digital
Baleen Specialty	21,431	2.5	%	1,630		0.2	%	19,801	1214.8	%
Express	2,370	0.3	%	—		—	%	2,370	NM
Digital	23,801	2.8	%	1,630		0.2	%	22,171	1360.2	%
Gross written premiums		100.0	%	$	695,717	100.0	%		24.0	%

All values are in US Dollars.

__________________

(1)Our products are delivered through two complementary underwriting models designed to support sustainable and profitable growth across market cycles: a “craft” model for large, complex, higher-severity risks, and a “digital” model, which includes Baleen Specialty and other small-business offerings (“express”), for smaller, simpler, scalable business.

Loss Ratio

The following tables summarize current and prior accident year loss ratios for the three and twelve months ended December 31, 2025 and 2024:

	Three Months Ended December 31,
	2025			2024
	Net Losses and Loss Adjustment Expenses	% of Net Earned Premiums		Net Losses and Loss Adjustment Expenses		% of Net Earned Premiums
	( in thousands, except percentages)
Current accident year		67.5	%	$	66,937	62.6	%
Prior accident year(1)	361	0.3	%	—		—	%
Total		67.8	%	$	66,937	62.6	%

All values are in US Dollars.

	Twelve Months Ended December 31,
	2025			2024
	Net Losses and Loss Adjustment Expenses	% of Net Earned Premiums		Net Losses and Loss Adjustment Expenses		% of Net Earned Premiums
	( in thousands, except percentages)
Current accident year		66.2	%	$	248,099	64.4	%
Prior accident year(1)	2,369	0.5	%	—		—	%
Total		66.7	%	$	248,099	64.4	%

All values are in US Dollars.

__________________

(1)Prior accident year loss ratios for the three and twelve months ended December 31, 2025 were driven by expected loss ratios applied to audit premiums fully earned in the period, but associated with prior accident years. This increase was not based on actual losses settling for more than reserved, and did not represent an increase in estimated reserves on unresolved claims.

Expense Ratio

The following tables summarize the components of our expense ratios for the three and twelve months ended December 31, 2025 and 2024:

	Three Months Ended December 31,
	2025			2024
	Expenses	% of Net Earned Premiums		Expenses		% of Net Earned Premiums
	( in thousands, except percentages)
Net acquisition costs		9.8	%	$	9,130	8.5	%
Operating expenses	26,640	19.8	%	23,352		21.9	%
Less: Other insurance-related income	(735)	(0.5)	%	(274)		(0.3)	%
Total		29.1	%	$	32,208	30.1	%

All values are in US Dollars.

	Twelve Months Ended December 31,
	2025					2024
	Expenses	% of Net Earned Premiums				Expenses		% of Net Earned Premiums
	( in thousands, except percentages)
Net acquisition costs		9.5	%			$	32,397	8.4	%
Operating expenses	102,264	20.8	%			89,112		23.1	%
Less: Other insurance-related income	(2,042)	(0.4)	%			(444)		(0.1)	%
Total		29.8	%	$	—	$	121,065	31.4	%

All values are in US Dollars.

Net Investment Income

The following table summarizes the sources of net investment income for the three and twelve months ended December 31, 2025 and 2024:

	Three Months Ended December 31,			Twelve Months Ended December 31,
	2025	2024		2025		2024
	( in thousands)
U.S. government and government agency		$	3,198	$	5,926	$	14,514
State and municipal	1,283	591		3,904		1,832
Commercial mortgage-backed securities	1,944	981		5,808		2,584
Residential mortgage-backed securities	3,903	2,399		13,060		6,517
Asset-backed securities	1,650	1,283		6,375		3,043
Corporate	5,247	2,154		17,459		5,768
Short-term investments	—	130		214		480
Cash and cash equivalents	1,964	1,700		6,244		6,193
Gross investment income	16,877	12,436		58,990		40,931
Investment expenses	(324)	(243)		(1,163)		(810)
Net investment income		$	12,193	$	57,827	$	40,121

All values are in US Dollars.

Reconciliation of Non-GAAP Financial Measures

This earnings release contains certain financial measures that are not presented in accordance with generally

accepted accounting principles in the United States (“U.S. GAAP”). We use these non-GAAP financial measures

when planning, monitoring and evaluating our performance. Management believes that each of the non-GAAP

financial measures described below provides useful insight into our underlying business performance.

•Adjusted net income is defined as net income excluding the impact of net realized investment gains (losses), non-operating expenses, loss on extinguishment of credit facility, foreign exchange losses (gains), and certain strategic initiatives. Adjusted net income excludes the impact of certain items that may not be indicative of underlying business trends, operating results, or future outlook, net of tax impact. We calculate the tax impact only on adjustments that would be included in calculating our income tax expense using the estimated tax rate at which we received a deduction for these adjustments.

•Adjusted return on equity is defined as adjusted net income as a percentage of average beginning and ending mezzanine equity and stockholders’ equity.

•Diluted adjusted earnings per share is defined as adjusted net income divided by the weighted average common shares outstanding for the period, reflecting the dilution that may occur if equity based awards are converted into common stock equivalents as calculated using the treasury stock method.

You should not rely on these non-GAAP financial measures as a substitute for any U.S. GAAP financial measure.

While we believe that these non-GAAP financial measures are useful in evaluating our business, this information

should be considered supplemental in nature and not as a replacement for or superior to the comparable U.S. GAAP

measures. In addition, other companies, including companies in our industry, may calculate such measures

differently, which reduces their usefulness as comparative measures.

Adjusted net income

Adjusted net income for the three and twelve months ended December 31, 2025 and 2024 reconciles to net income as follows:

	Three Months Ended December 31,
	2025			2024
	Before Income Taxes	After Income Taxes		Before Income Taxes		After Income Taxes
	( in thousands)
Income as reported		$	14,844	$	18,249	$	13,607
Adjustments:
Net realized investment (gains)	(73)	(73)		—		—
Non-operating expenses	95	95		622		622
Loss on extinguishment of credit facility	862	862		—		—
Foreign exchange (gains) losses	(14)	(14)		1		1
Tax impact	—	(183)		—		(131)
Adjusted net income		$	15,531	$	18,872	$	14,099

All values are in US Dollars.

	Twelve Months Ended December 31,
	2025			2024
	Before Income Taxes	After Income Taxes		Before Income Taxes		After Income Taxes
	( in thousands)
Income as reported		$	53,786	$	50,535	$	38,243
Adjustments:
Net realized investment (gains) losses	(43)	(43)		16		16
Non-operating expenses	1,425	1,425		2,807		2,807
Loss on extinguishment of credit facility	862	862		—		—
Foreign exchange losses	50	50		68		68
Strategic initiatives(1)	—	—		2,733		2,733
Tax impact	—	(482)		—		(1,181)
Adjusted net income		$	55,598	$	56,159	$	42,686

All values are in US Dollars.

_________________

(1)Strategic initiatives for the twelve months ended December 31, 2024 represents costs incurred to set up our Baleen Specialty division, which is recorded in operating expenses within the Consolidated Statements of Income and Comprehensive Income. The costs incurred primarily represent expenses to implement the new platform and processes supporting the Baleen Specialty division.

Adjusted return on equity

Adjusted return on equity for the three and twelve months ended December 31, 2025 and 2024 reconciles to return on equity as follows:

	Three Months Ended December 31,					Twelve Months Ended December 31,
	2025		2024			2025			2024
	( in thousands, except percentages)
Numerator: Adjusted net income(1)			$	56,395		$	55,598		$	42,686
Denominator: Average mezzanine equity and stockholders' equity	440,156		367,467			409,858			281,259
Adjusted return on equity	14.1	%	15.3		%	13.6		%	15.2		%

All values are in US Dollars.

_______________

(1)For the three months ended December 31, 2025 and 2024, net income and adjusted net income are annualized to arrive at return on equity and adjusted return on equity.

Diluted adjusted earnings per share

Diluted adjusted earnings per share for the three and twelve months ended December 31, 2025 and 2024 reconciles to diluted earnings per share as follows:

	Three Months Ended December 31,			Twelve Months Ended December 31,
	2025	2024		2025		2024
	( in thousands, except share and per share data)
Numerator: Adjusted net income		$	14,099	$	55,598	$	42,686
Denominator: Diluted weighted average shares outstanding	33,395,657	33,571,535		33,735,944		29,677,196
Diluted adjusted earnings per share		$	0.42	$	1.65	$	1.44

All values are in US Dollars.

About Bowhead Specialty Holdings Inc.

Bowhead Specialty is a growing specialty insurance business providing casualty, professional liability and healthcare liability insurance products. We were founded and are led by industry veteran Stephen Sills. The team is composed of highly experienced and respected industry veterans with decades of individual, successful underwriting and management experience. Our products are delivered through two complementary underwriting models designed to support sustainable and profitable growth across market cycles: a “craft” model for large, complex, higher-severity risks, and a “digital” model, which includes Baleen Specialty and other small-business offerings (“express”), for smaller, simpler, and scalable business.

We pride ourselves on the quality and experience of our people, who are committed to exceeding our partners’ expectations through excellent service and expertise. Our collaborative culture spans all functions of our business and allows us to provide a consistent, positive experience for all of our partners.

Conference Call

The Company will host a conference call to discuss its results on the same day, Tuesday, February 24, 2026, beginning at 8:30 a.m. Eastern Time. Interested parties may access the conference call through a live webcast, which can be accessed by going to https://bowhead-4q25-earnings-call.open-exchange.net/registration, or by visiting the Company’s Investor Relations website. A dial-in option for listen-only participants will be available after registering for the call. Please join the live webcast or dial in at least 10 minutes before the start of the call.

A replay of the event webcast will be available on the Company’s Investor Relations website for one year following the call.

Forward-Looking Statements

This press release contains forward-looking statements as that term is defined in the Private Securities Litigation Reform Act of 1995. All statements other than statements of historical facts contained in press release are forward-looking statements. In some cases, forward-looking statements can be identified by terms such as "anticipates," "believes," "estimates," "expects," "intends," "plans," "predicts," "projects," "seeks," "future," "outlook," "prospects" "will," "would," "should," "could," "may," "can have" or similar words. Forward-looking statements involve risks and uncertainties that could cause actual results to differ materially from those contemplated by the forward-looking statements. These risks include those described in the Company’s filings made with the Securities and Exchange Commission. Forward-looking statements speak only as of the date of this press release and the Company does not undertake any obligation to update or revise any forward-looking information to reflect changes in assumptions, the occurrence of unanticipated events or otherwise.

Investor Relations Contact:

Shirley Yap, Head of Investor Relations

investorrelations@bowheadspecialty.com

q42025bowheadinvestordec

Investor Presentation February 2026

COLOR PALETTE Text 50 56 62 Title bar/ Bullets 1 23 65 ACCEN TS 1 1 23 65 80 139 252 2 0 148 255 153 212 255 3 234 71 36 247 181 167 4 164 148 31 235 225 149 5 121 26 104 229 135 213 6 83 161 209 186 217 237 Hyperlink 0 148 255 153 212 255 Followed Hyperlink 234 71 36 247 181 167 Line s 50 56 62 Highlights 1 23 65 TABL E 2 Forward-Looking Statements and Other Notices This presentation has been prepared by Bowhead Specialty Holdings Inc. (“we,” “us,” “our,” “Bowhead” or the “Company”) on a confidential basis for the exclusive use of the party to whom Bowhead delivers this presentation. This presentation has been prepared by Bowhead for informational purposes only and not for any other purpose. Nothing contained in this presentation is, or should be construed as, a recommendation, promise or representation by the presenter or Bowhead or any officer, director, employee, agent or advisor of Bowhead. This presentation does not purport to be all inclusive or to contain all of the information you may desire. Information provided in this presentation speaks only as of the date hereof. Bowhead assumes no obligation to update any information or statement after the date of this presentation as a result of new information, subsequent events, or any other circumstances. We request that you keep any information at this meeting confidential and that you do not disclose any of the information to any other parties without the Company's prior express written permission. This presentation contains “forward-looking statements” within the meaning of the Private Securities Litigation Reform Act of 1995. All statements other than statements of historical facts contained in this presentation, including statements regarding our future results of operations or financial condition, business strategy and plans, and objectives of management for future operations are forward-looking statements. Some of the forward-looking statements can be identified by the use of terms such as “believes”, “expects”, “may”, “will”, “should”, “could”, “seeks”, “intends”, “plans”, “estimates”, “anticipates” or other comparable terms. However, not all forward-looking statements contain these identifying words. These forward-looking statements include all matters that are not related to present facts or current conditions or that are not historical facts. They appear in a number of places throughout this presentation and include statements regarding our intentions, beliefs or current expectations concerning, among other things, our consolidated results of operations, financial condition, liquidity, prospects and growth strategies and the industries in which we operate, and include, without limitation, statements relating to our future performance. Forward-looking statements are subject to known and unknown risks and uncertainties, many of which are beyond our control. Our actual results may differ materially from those expressed in, or implied by, the forward-looking statements included in this presentation as a result of various factors, including, among others, the factors discussed under the heading “Risk Factors” in our Annual Report on Form 10-K for the year ended December 31, 2024 and our Quarterly Report on the Form 10-Q for the three months ended March 31, 2025, as well as our other filings with the Securities and Exchange Commission. The forward-looking statements made in this presentation relate only to events as of the date on which the statements are made. We undertake no obligation to update any forward-looking statements made in this presentation to reflect events or circumstances after the date of this presentation or to reflect new information or the occurrence of unanticipated events, except as required by law. We may not actually achieve the plans, intentions, or expectations disclosed in our forward-looking statements, and you should not place undue reliance on our forward-looking statements. Unless otherwise indicated, information contained in this presentation concerning our industry and the markets in which we operate, including our general expectations, market position and market opportunity, is based on our management’s estimates and research, as well as industry and general publications and research, surveys and studies conducted by third parties. Industry publications, studies and surveys generally state that they have been obtained from sources believed to be reliable, although they do not guarantee the accuracy or completeness of such information. We believe that the information from these third-party publications, research, surveys and studies included in this presentation is reliable. Management’s estimates are derived from publicly available information, their knowledge of our industry and their assumptions based on such information and knowledge, which we believe to be reasonable. This data involves a number of assumptions and limitations which are necessarily subject to a high degree of uncertainty and risk due to a variety of factors. These and other factors could cause our future performance to differ materially from our assumptions and estimates. This presentation contains references to our trademarks and service marks and to those belonging to other entities. Solely for convenience, trademarks and trade names referred to in this presentation may appear without the ® or ™ symbols, but such references are not intended to indicate, in any way, that we will not assert, to the fullest extent under applicable law, our rights or the rights of the applicable licensor to these trademarks and trade names. We do not intend our use or display of other companies’ trade names, trademarks or service marks to imply a relationship with, or endorsement or sponsorship of us by, any other companies. “Non-admitted” or excess and surplus (“E&S”) lines refers to policies generally not subject to regulations governing premium rates or policy language. We also consider business written on (i) a facultative reinsurance basis or (ii) an admitted basis through either the New York Free Trade Zone or similar commercial deregulation exemptions available in certain jurisdictions, to be E&S business since such business is generally free of rate and form restrictions. This presentation contains certain financial measures that are not presented in accordance with generally accepted accounting principles in the United States (“U.S. GAAP”). Under U.S. securities laws, these measures are called “non-GAAP financial measures.” We use these non-GAAP financial measures when planning, monitoring and evaluating our performance. We believe these non-GAAP financial measures give our management and other users of our financial information useful insight into our underlying business performance. You should not rely on these non-GAAP financial measures as a substitute for any U.S. GAAP financial measure. While we believe that these non-GAAP financial measures are useful in evaluating our business, this information should be considered supplemental in nature and is not meant to be an alternative to our reported results prepared in accordance with U.S. GAAP. In addition, other companies, including companies in our industry, may calculate such measures differently, which reduces their usefulness as comparative measures. For a reconciliation of such non-GAAP financial measures to the most directly comparable U.S. GAAP financial measures, see the Appendix of this presentation.

9 Business Mix vs. Specialty Peers GWP CAGR (2021-2024) Source: Company filings, S&P Global. 1 Represents statutory premium for each company's SNL P&C Group. Long-Tail lines include Commercial Multi Peril, Fidelity & Surety, Medical Professional Liability, Other/Product Liability, and Workers’ Compensation. Short-Tail lines include Accident & Health, Aircraft, Commercial Auto, Financial & Mortgage Guaranty, Fire & Allied, Homeowners/Farmowners, Marine Lines, Other Commercial, and Private Auto. 2024 Long-Tail Premium as a % of Total Premium1 1 78.4%95.1% 76.8%3-Year Average Combined Ratio 92.3%85.7%90.1% 95.2% 91.2% 2024 Long-Tail Premium as a % of Total Premium Bowhead writes a low volatility book of business that produces consistent and profitable results 100% 71% 67% 61% 53% 52% 51% 31%

DRAFT: 3/1/2024 Financials

DRAFT: 3/1/2024 Appendix