Skyward/2025/FY/Annual report

Document info
Organization	Skyward
Year	2025
Period	FY
Period label	FY25
Document type	Annual report
Document name	Skyward Specialty Insurance Group 2025 Form 10-K
Publication date	2026-03-02
Language	English
Source	Original URL

This article presents Skyward's FY 2025 annual report — the cover and primary financial statements from its SEC Form 10-K.

Cover

USD ($)	12 Months Ended
—	Dec. 31, 2025	Feb. 26, 2026	Jun. 30, 2025
Cover [Abstract]	—	—	—
Document Type	10-K	—	—
Document Annual Report	true	—	—
Document Period End Date	Dec. 31, 2025	—	—
Current Fiscal Year End Date	--12-31	—	—
Document Transition Report	false	—	—
Entity File Number	001-41591	—	—
Entity Registrant Name	SKYWARD SPECIALTY INSURANCE GROUP, INC.	—	—
Entity Incorporation, State or Country Code	DE	—	—
Entity Tax Identification Number	14-1957288	—	—
Entity Address, Address Line One	800 Gessner Road	—	—
Entity Address, Address Line Two	Suite 600	—	—
Entity Address, City or Town	Houston	—	—
Entity Address, State or Province	TX	—	—
Entity Address, Postal Zip Code	77024-4284	—	—
City Area Code	713	—	—
Local Phone Number	935-4800	—	—
Title of 12(b) Security	Common stock, par value $0.01	—	—
Trading Symbol	SKWD	—	—
Security Exchange Name	NASDAQ	—	—
Entity Well-known Seasoned Issuer	No	—	—
Entity Voluntary Filers	No	—	—
Entity Current Reporting Status	No	—	—
Entity Interactive Data Current	Yes	—	—
Entity Filer Category	Large Accelerated Filer	—	—
Entity Small Business	false	—	—
Entity Emerging Growth Company	false	—	—
ICFR Auditor Attestation Flag	true	—	—
Document Financial Statement Error Correction [Flag]	false	—	—
Entity Shell Company	false	—	—
Entity Public Float	—	—	2,165,161,643
Entity Common Stock, Shares Outstanding	—	44,467,084	—
Documents Incorporated by Reference	Portions of the Registrant’s Proxy Statement relating to the 2026 annual meeting of stockholders (the “2026 Proxy Statement”), which will be filed within 120 days of December 31, 2025, are incorporated by reference into Part III of this Form 10-K.	—	—
Entity Central Index Key	0001519449	—	—
Amendment Flag	false	—	—
Document Fiscal Year Focus	2025	—	—
Document Fiscal Period Focus	FY	—	—

Audit Information

	12 Months Ended
—	Dec. 31, 2025
Audit Information [Abstract]	—
Auditor Name	Ernst & Young LLP
Auditor Location	Houston, Texas
Auditor Firm ID	42

Consolidated balance sheets

USD ($) $ in Thousands	Dec. 31, 2025	Dec. 31, 2024
Investments:	—	—
Fixed maturity securities, available-for-sale, at fair value (net of allowance for credit losses of $7,000 and $0, respectively) (amortized cost of $1,848,755 and $1,320,266, respectively)	1,856,303	1,292,218
Fixed maturity securities, held-to-maturity, at amortized cost (net of allowance for credit losses of $468 and $243, respectively)	32,822	39,153
Equity securities, at fair value	1,174	106,254
Mortgage loans, at fair value	9,902	26,490
Equity method investments	77,365	98,594
Other long-term investments	58,650	33,182
Short-term investments, at fair value	264,299	274,929
Total investments	2,300,515	1,870,820
Cash and cash equivalents	168,544	121,603
Restricted cash	30,570	35,922
Premiums receivable, net	544,217	321,641
Reinsurance recoverables, net	1,119,880	857,876
Ceded unearned premium	238,948	203,901
Deferred policy acquisition costs	136,100	113,183
Deferred income taxes	27,865	30,486
Goodwill and intangible assets, net	88,040	87,348
Other assets	137,173	86,698
Total assets	4,791,852	3,729,478
Liabilities:	—	—
Reserves for losses and loss adjustment expenses	2,318,894	1,782,383
Unearned premiums	774,035	637,185
Deferred ceding commission	46,453	40,434
Reinsurance and premium payables	279,888	177,070
Funds held for others	128,003	102,665
Accounts payable and accrued liabilities	115,034	76,206
Carrying Value	100,411	100,000
Subordinated debt, net of debt issuance costs	19,569	19,536
Total liabilities	3,782,287	2,935,479
Stockholders’ equity	—	—
Common stock, $0.01 par value, 500,000,000 shares authorized, 40,511,222 and 40,127,908 shares issued and outstanding, respectively	405	401
Additional paid-in capital	730,555	718,598
Accumulated other comprehensive income (loss)	11,457	-22,120
Retained earnings	267,148	97,120
Total stockholders’ equity	1,009,565	793,999
Total liabilities and stockholders’ equity	4,791,852	3,729,478

Consolidated balance sheets (parenthetical)

USD ($) $ in Thousands	Dec. 31, 2025	Dec. 31, 2024
Statement of Financial Position [Abstract]	—	—
Available-for-sale allowance for credit losses	7,000	0
Amortized cost	1,848,755	1,320,266
Allowance for credit losses	468	243
Common stock, par value (in dollar per share)	0.01	0.01
Common stock, shares authorized (in shares)	500,000,000	500,000,000
Common stock, shares issued (in shares)	40,511,222	40,127,908
Common stock, shares outstanding (in shares)	40,511,222	40,127,908

Consolidated statements of operations and comprehensive income

USD ($) $ in Thousands	12 Months Ended
—	Dec. 31, 2025	Dec. 31, 2024	Dec. 31, 2023
Revenues:	—	—	—
Net earned premiums	1,304,505	1,056,722	829,143
Commission and fee income	6,855	6,703	6,064
Net investment income	83,619	80,600	40,340
Net investment gains	22,149	6,342	11,054
Other loss	-587	-167	-632
Total revenues	1,416,541	1,150,200	885,969
Expenses:	—	—	—
Losses and loss adjustment expenses	795,022	669,809	515,237
Underwriting, acquisition and insurance expenses	377,359	311,757	243,444
Transaction costs	14,019	0	0
Interest expense	7,919	9,496	10,024
Amortization expense	1,636	2,007	1,798
Other expenses	4,162	4,392	5,364
Total expenses	1,200,117	997,461	775,867
Income before income taxes	216,424	152,739	110,102
Income tax expense	46,396	33,911	24,118
Net income	170,028	118,828	85,984
Net income attributable to participating securities	0	0	1,677
Net income attributable to common stockholders	170,028	118,828	84,307
Comprehensive income	—	—	—
Net income	170,028	118,828	85,984
Unrealized gains and losses on investments:	—	—	—
Net change in unrealized gains on investments, net of tax	33,092	9,792	25,516
Reclassification adjustment for gains (losses) on securities no longer held, net of tax	485	-8,959	-4,984
Total other comprehensive income	33,577	833	20,532
Comprehensive income	203,605	119,661	106,516
Per share data:	—	—	—
Basic earnings per share (in dollar per share)	4.21	2.97	2.34
Diluted earnings per share (in dollar per share)	4.07	2.87	2.24
Weighted-average common shares outstanding	—	—	—
Basic (in shares)	40,407,310	40,056,475	36,031,907
Diluted (in shares)	41,808,046	41,377,460	38,317,534

Consolidated statements of stockholders’ equity

USD ($) $ in Thousands	Total	Preferred stocks:	Common stock:	Treasury stock:	Additional paid-in capital:	Stock notes receivable:	Accumulated other comprehensive income (loss):	Retained earnings (accumulated deficit):	Retained earnings (accumulated deficit): Period of adoption, adjustment
Preferred shares balance at beginning of period (in shares) at Dec. 31, 2022	—	1,969,660	—	—	—	—	—	—	—
Increase (Decrease) in Stockholders' Equity [Roll Forward]	—	—	—	—	—	—	—	—	—
Preferred stock conversion to common shares (in shares)	—	-1,969,660	16,305,113	—	—	—	—	—	—
Preferred shares balance at ending of period (in shares) at Dec. 31, 2023	—	0	—	—	—	—	—	—	—
Common shares balance at beginning of period (in shares) at Dec. 31, 2022	—	—	16,599,666	—	—	—	—	—	—
Increase (Decrease) in Stockholders' Equity [Roll Forward]	—	—	—	—	—	—	—	—	—
Issuance of shares (in shares)	—	—	6,958,977	—	—	—	—	—	—
Common shares balance at ending of period (in shares) at Dec. 31, 2023	—	—	39,863,756	—	—	—	—	—	—
Stockholders' equity beginning balance at Dec. 31, 2022	—	20	168	-2	577,289	-6,911	-43,485	-105,417	-2,275
Increase (Decrease) in Stockholders' Equity [Roll Forward]	—	—	—	—	—	—	—	—	—
Preferred stock conversion to common shares	—	-20	161	2	-143	—	—	—	—
Issuance of common stock/Employee equity transactions	—	—	22	—	9,213	1,349	—	—	—
Proceeds from equity offerings, net	—	—	48	—	124,496	—	—	—	—
Other comprehensive income, net of tax	20,532	—	—	—	—	—	20,532	—	—
Net income	85,984	—	—	—	—	—	—	85,984	—
Stockholders' equity ending balance at Dec. 31, 2023	661,031	0	399	0	710,855	-5,562	-22,953	-21,708	0
Increase (Decrease) in Stockholders' Equity [Roll Forward]	—	—	—	—	—	—	—	—	—
Preferred stock conversion to common shares (in shares)	—	0	0	—	—	—	—	—	—
Preferred shares balance at ending of period (in shares) at Dec. 31, 2024	—	0	—	—	—	—	—	—	—
Increase (Decrease) in Stockholders' Equity [Roll Forward]	—	—	—	—	—	—	—	—	—
Issuance of shares (in shares)	—	—	264,152	—	—	—	—	—	—
Common shares balance at ending of period (in shares) at Dec. 31, 2024	40,127,908	—	40,127,908	—	—	—	—	—	—
Increase (Decrease) in Stockholders' Equity [Roll Forward]	—	—	—	—	—	—	—	—	—
Preferred stock conversion to common shares	—	0	0	0	0	—	—	—	—
Issuance of common stock/Employee equity transactions	—	—	2	—	7,743	5,562	—	—	—
Proceeds from equity offerings, net	—	—	0	—	0	—	—	—	—
Other comprehensive income, net of tax	833	—	—	—	—	—	833	—	—
Net income	118,828	—	—	—	—	—	—	118,828	—
Stockholders' equity ending balance at Dec. 31, 2024	793,999	0	401	0	718,598	0	-22,120	97,120	0
Increase (Decrease) in Stockholders' Equity [Roll Forward]	—	—	—	—	—	—	—	—	—
Preferred stock conversion to common shares (in shares)	—	0	0	—	—	—	—	—	—
Preferred shares balance at ending of period (in shares) at Dec. 31, 2025	—	0	—	—	—	—	—	—	—
Increase (Decrease) in Stockholders' Equity [Roll Forward]	—	—	—	—	—	—	—	—	—
Issuance of shares (in shares)	—	—	383,314	—	—	—	—	—	—
Common shares balance at ending of period (in shares) at Dec. 31, 2025	40,511,222	—	40,511,222	—	—	—	—	—	—
Increase (Decrease) in Stockholders' Equity [Roll Forward]	—	—	—	—	—	—	—	—	—
Preferred stock conversion to common shares	—	0	0	0	0	—	—	—	—
Issuance of common stock/Employee equity transactions	—	—	4	—	11,957	0	—	—	—
Proceeds from equity offerings, net	—	—	0	—	0	—	—	—	—
Other comprehensive income, net of tax	33,577	—	—	—	—	—	33,577	—	—
Net income	170,028	—	—	—	—	—	—	170,028	—
Stockholders' equity ending balance at Dec. 31, 2025	1,009,565	0	405	0	730,555	0	11,457	267,148	—

Consolidated statements of cash flows

USD ($) $ in Thousands	12 Months Ended
—	Dec. 31, 2025	Dec. 31, 2024	Dec. 31, 2023
Cash flows from operating activities:	—	—	—
Net income	170,028	118,828	85,984
Net investment (gains) losses	-22,149	-6,342	-11,054
Depreciation and amortization expense	3,535	3,358	3,891
Stock-based compensation expense	11,960	9,395	8,525
Undistributed earnings (loss) from long-term investments	10,122	-6,252	6,730
Net change in fair value of derivatives	-34,857	0	0
Deferred income tax, net	-6,397	-8,708	9,383
Premiums receivable, net	-222,576	-142,406	-40,020
Reinsurance recoverables, net	-262,004	-261,542	-17,270
Ceded unearned premium	-35,047	-17,780	-28,476
Deferred policy acquisition costs	-22,917	-21,228	-23,017
Federal income taxes	1,797	4,500	-1,892
Losses and loss adjustment expenses	536,511	467,882	172,744
Unearned premiums	136,850	84,653	110,023
Deferred ceding commission	6,019	3,377	7,208
Reinsurance and premium payables	102,818	26,914	36,460
Funds held for others	25,338	44,077	21,730
Accounts payable and accrued liabilities	37,032	19,177	2,285
Other, net	-27,987	-12,788	-5,047
Net cash provided by operating activities	408,076	305,115	338,187
Cash flows from investing activities:	—	—	—
Purchase of fixed maturity securities, available-for-sale	-910,039	-617,606	-459,672
Purchase of illiquid investments	0	-75	-1,675
Purchase of equity securities	-13,213	-14,077	-26,009
Purchase of equity method investments and other long-term investments	-6,814	-32,173	0
Purchase of intangible assets and goodwill	-2,000	0	-50
Investment in direct and indirect loans	19,674	27,480	2,984
Purchase of property and equipment	-5,454	-4,224	-3,108
Proceeds from the sales of fixed maturity securities, available-for-sale	198,195	217,468	26,626
Maturities, calls, transfers and paydowns of fixed maturity securities, available-for-sale	183,951	122,694	48,957
Maturities, calls and paydowns of fixed maturity securities held-to-maturity	4,357	6,015	11,444
Proceeds from the sales of equity securities	126,738	37,534	40,201
Sales of and distributions from equity method and other long-term investments	11,902	14,073	3,572
Change in short-term investments	10,626	-4,799	-149,068
Change in receivable/payable for securities	11,928	34	76
Cash provided by deposit accounting	3,251	3,962	11,913
Net cash used in investment activities	-366,898	-243,694	-493,809
Cash flows from financing activities:	—	—	—
Employee share purchases	0	0	1,350
Repayment of stock notes receivable	0	5,562	0
Proceeds from long term borrowings	43,411	107,000	50,000
Payments on long term borrowings and trust preferred	-43,000	-116,794	-50,000
Proceeds from initial public offering	0	0	129,597
Net cash provided by (used in) financing activities	411	-4,232	130,947
Net increase (decrease) in cash and cash equivalents and restricted cash	41,589	57,189	-24,675
Cash and cash equivalents and restricted cash at beginning of period	157,525	100,336	125,011
Cash and cash equivalents and restricted cash at end of period	199,114	157,525	100,336
Supplemental disclosure of cash flow information:	—	—	—
Cash paid for interest	6,149	8,573	10,667