Form 8-K

8-K — Skyward Specialty Insurance Group, Inc.

Accession: 0001519449-26-000059

Filed: 2026-11-05

Period: 2026-11-05

CIK: 0001519449

SIC: 6331 (FIRE, MARINE & CASUALTY INSURANCE)

Item: Results of Operations and Financial Condition

Item: Financial Statements and Exhibits

Documents

8-K — skwd-20261105.htm (Primary)

EX-99.1 (earningsrelease-ex9913q2026.htm)

GRAPHIC (picture2.jpg)

XML — IDEA: XBRL DOCUMENT (R1.htm)

8-K

8-K (Primary)

Filename: skwd-20261105.htm · Sequence: 1

skwd-20261105

false000151944900015194492026-11-052026-11-05

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): November 5, 2026

___________________________________

Skyward Specialty Insurance Group, Inc.

(Exact name of registrant as specified in its charter)

___________________________________

Delaware

(State or other jurisdiction of

incorporation or organization)

001-41591

(Commission File Number)

14-1957288

(I.R.S. Employer Identification Number)

800 Gessner Road, Suite 600

Houston, Texas

77024-4284

(Address of principal executive offices and zip code)

(Zip Code)

(713) 935-4800

(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

Name of each exchange on which registered

Common stock, par value $0.01

SKWD

The Nasdaq Stock Market LLC

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

☐

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 November 5, 2026, Skyward Specialty Insurance Group, Inc. (the “Company”) issued a press release announcing the results of the Company’s operations for the quarter and fiscal period ended September 30, 2026. The press release is furnished as Exhibit 99.1 to this Report and is hereby incorporated by reference in this Item 2.02.

As provided in General Instruction B.2 of Form 8-K, the information and exhibits contained in this Form 8-K shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, nor shall they be deemed to be incorporated by reference in any filing under the Securities Act of 1933, as amended, except as shall be expressly set forth by specific reference in such a filing.

Forward-Looking Statements

Statements made in this Current Report on Form 8-K, other than those concerning historical information, should be considered forward-looking statements pursuant to the safe harbor provisions of the Securities Exchange Act of 1934 and the Private Securities Litigation Act of 1995. These forward-looking statements involve risks and uncertainties and are based on the beliefs and assumptions of management and on the information available to management at the time that this report was prepared. These statements can be identified by the use of words like “expect,” “anticipate,” “estimate,” and “believe,” variations of these words and other similar expressions. Readers should not place undue reliance on forward-looking statements as a number of important factors could cause actual results to differ materially from those in the forward-looking statements. Factors that might cause such a difference include, but are not limited to, changes in interest rate environment, management’s business strategy, national, regional, and local market conditions and legislative and regulatory conditions.

Item 9.01.

Financial Statements and Exhibits

(d)

Exhibits

Exhibit No.

Description

99.1

Press Release dated November 5, 2026

104.1

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.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

Date:

November 5, 2026

/s/ Mark Haushill

Mark Haushill

Chief Financial Officer

EX-99.1

Filename: earningsrelease-ex9913q2026.htm · Sequence: 2

Document

Exhibit 99.1

Skyward Group Reports Third Quarter 2026 Results

Houston, TX – November 5, 2026 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Group” or the “Company”) today reported third quarter 2026 results.

Summary Financial Data

($ in thousands, except per share amounts) Three months ended September 30, Nine months ended September 30,

unaudited 2026 2025 2026 2025

Managed premiums(1)

$ 1,320,600 $ 1,174,191 $ 3,346,984 $ 2,884,425

Gross written premiums(1)(2)

$ 803,485 $ 737,288 $ 2,211,743 $ 1,985,719

Fee generating gross written premiums(1)(2)

$ 517,115 $ 436,903 $ 1,135,241 $ 898,706

Net written premiums $ 501,778 $ 441,167 $ 1,420,277 $ 1,123,651

Net income $ 49,796 $ 45,901 $ 148,565 $ 126,798

Net operating income(3)

$ 58,486 $ 44,228 $ 174,577 $ 119,512

Diluted earnings per share $ 1.09 $ 1.10 $ 3.26 $ 3.03

Diluted operating earnings per share $ 1.28 $ 1.05 $ 3.83 $ 2.84

Annualized ROE (4)

15.7 % 19.7 % 17.3 % 19.3 %

Annualized operating ROE (5)

18.4 % 19.0 % 20.4 % 18.2 %

(1) Select third quarter 2025 metrics for the Skyward Group and Apollo are presented on a pro forma basis for comparative purposes only and are not necessarily indicative of the operating results that Skyward Group would have recognized had the acquisition actually been completed on January 1, 2025. Pro forma information is unaudited.

(2) Prior year pro forma gross written premiums are adjusted for the impact of the change in participations. See “Reconciliation of Non-GAAP Financial Measures”.

(3) See “Reconciliation of Non-GAAP Financial Measures”

(4) Annualized ROE is net income expressed on an annualized basis as a percentage of average beginning and ending stockholders' equity during the period.

(5) Annualized operating ROE is operating income expressed on an annualized basis as a percentage of average beginning and ending stockholders' equity during the period.

Highlights for the third quarter included:

•Managed premiums increased 12.5%(2) compared to 2025;

•Gross written premiums increased 9.0%(1)(2) compared to 2025;

•Fee-generating gross written premiums(1)(2) increased 18.4% compared to 2025;

•Combined ratio of 89.9%;

•Ex-Cat combined ratio of 88.1%;

•Annualized return on equity(4) and annualized operating return on equity(5) of 17.3% and 20.4%, respectively, for the nine months ended September 30, 2026; and,

•Book value per share of $28.74, an increase of 15.3% compared to December 31, 2025.

Skyward Group Chairman and CEO Andrew Robinson commented, “The outstanding quarter and year to date performance reflects the strength of the Skyward Group Rule Our NicheTM strategy and the benefits of the diversified portfolio we have built. Through the first nine months of the year, we have delivered an annualized operating ROE of over 20% while growing managed premiums by 16%. In the quarter, gross written premiums grew 9.0%, while fee-generating gross written premiums increased 18%. The diversity of our portfolio and the complementary strength of our capital-light, fee-based platform continue to be meaningful differentiators, providing multiple avenues for profitable growth and enabling us to remain disciplined in deploying capital toward the most compelling opportunities as market conditions evolve. Across Skyward Group, we continue to execute at a high level, and we remain well positioned to continue to deliver top-quartile financial returns for our shareholders.”

Results of Operations

Gross Written Premiums By Underwriting Division

($ in thousands) Three months ended September 30, Nine months ended September 30,

2026 2025 % Change 2026 2025 % Change

Skyward Specialty Segment

Accident & Health $ 99,131 $ 63,147 57.0 % $ 286,596 $ 186,805 53.4 %

Captives 50,185 67,956 (26.2) % 172,350 211,879 (18.7) %

Credit & Surety 67,210 52,785 27.3 % 195,143 152,944 27.6 %

Energy Solutions 55,646 66,576 (16.4) % 167,202 216,992 (22.9) %

Global Agriculture 192,161 159,057 20.8 % 406,452 296,853 36.9 %

Global Property 22,318 27,649 (19.3) % 127,944 158,327 (19.2) %

Professional Lines 31,323 34,637 (9.6) % 102,529 112,409 (8.8) %

Strategic Distribution Partners 109,565 82,771 32.4 % 315,773 231,401 36.5 %

Transactional E&S 40,745 50,950 (20.0) % 143,105 156,417 (8.5) %

Total continuing business $ 668,284 $ 605,528 10.4 % $ 1,917,094 $ 1,724,027 11.2 %

Exited business (2) 981

NM(1)

765 2,722

NM(1)

Total Skyward Specialty Segment gross written premiums $ 668,282 $ 606,509 10.2 % $ 1,917,859 $ 1,726,749 11.1 %

Apollo Segment(2)(3)

Syndicate 1969 67,520 61,105 10.5 % 191,959 160,164 19.9 %

Syndicate 1971 67,683 69,674 (2.9) % 101,925 98,806 3.2 %

Total Apollo Segment gross written premiums 135,203 130,779 3.4 % 293,884 258,970 13.5 %

Total gross written premiums(2)(3)

$ 803,485 $ 737,288 9.0 % $ 2,211,743 $ 1,985,719 11.4 %

(1) Not meaningful.

(2) Prior year information is pro forma.

(3) Prior year information is adjusted for the impact of the change in participations. See “Reconciliation of Non-GAAP Financial Measures”.

Effective in the third quarter, the Company renamed the Specialty Programs division to Strategic Distribution Partners (or “Strategic “Distribution”) to better reflect the breadth of its distribution model, the Company’s ownership interests in many of these distributors, and its ability to incorporate U.S. distribution activities related to ibott within the division.

Managed Premiums

Apollo provides managing agency services to nine syndicates within its Lloyd’s platform. The capital-aligned syndicates, Syndicate 1969, Syndicate 1971 and Syndicate 1972, are wholly managed and partly capitalized by Apollo with Apollo retaining a portion of the underwriting risk via its Lloyd's Corporate Member, Apollo No. 16. Platform Partner syndicates are managed by Apollo on behalf of third‑party partners and Apollo does not currently provide capital for underwriting of these syndicates. Because managed premiums are a key management operating metric intended to reflect the scale of business managed by Apollo, inter-syndicate reinsurance transactions, including those involving Syndicate 1972 and other Apollo-managed syndicates, are not eliminated in the calculation of managed premiums. Apollo receives managing agency fees and performance‑based income for its managing agency services from all syndicates on its Lloyd's platform.

($ in thousands) Three months ended September 30, Nine months ended September 30,

2026 2025 % Change 2026 2025 % Change

Total gross written premiums(1)(2)

$ 803,485 $ 737,288 9.0% $ 2,211,743 $ 1,985,719 11.4%

Fee generating gross written premiums(1)(2):

Aligned Syndicates(3)

401,468 369,548 8.6% 855,183 717,178 19.2%

Partner Syndicates(3)

115,647 67,355 71.7% 280,058 181,528 54.3%

Total fee generating gross written premiums $ 517,115 $ 436,903 18.4% $ 1,135,241 $ 898,706 26.3%

Total Skyward Group managed premiums $ 1,320,600 $ 1,174,191 12.5% $ 3,346,984 $ 2,884,425 16.0%

(1) Prior year information is pro forma.

(2) Prior year information is adjusted for the impact of the change in participations. See “Reconciliation of Non-GAAP Financial Measures”.

(3) During the third quarter of 2026, the Company reclassified fee generating gross written premiums attributable to Syndicate 1972 from Partner Syndicates to Aligned Syndicates. Year to date 2026 amounts have been reclassified to conform to the current period presentation.

Underwriting Results

($ in thousands) Three Months Ended September 30, 2026 Nine Months Ended September 30, 2026

Skyward Specialty Apollo Corporate Total Skyward Specialty Apollo Corporate Total

Revenues:

Net earned premiums $ 329,958 $ 76,906 $ — $ 406,864 $ 1,072,247 $ 213,096 $ — $ 1,285,343

Underwriting fee income — 11,000 — 11,000 — 33,666 — 33,666

Commission and fee income 3,118 — — 3,118 6,979 — — 6,979

Total revenues 333,076 87,906 — 420,982 1,079,226 246,762 — 1,325,988

Expenses:

Losses and loss adjustment expenses 206,413 44,623 — 251,036 671,611 121,389 — 793,000

Underwriting, acquisition and insurance expenses 88,051 24,986 4,965 118,002 279,145 72,506 14,246 365,897

Fee‑based service expenses — 4,075 — 4,075 — 12,807 — 12,807

Total expenses 294,464 73,684 4,965 373,113 950,756 206,702 14,246 1,171,704

Underwriting Income $ 38,612 $ 14,222 $ — $ 47,869 $ 128,470 $ 40,060 $ — $ 154,284

Combined Ratio

Non-cat loss and LAE

61.1 % 55.2 % — % 59.9 % 60.9 % 54.3 % — % 59.9 %

Cat loss and LAE

1.5 % 2.8 % — % 1.8 % 1.7 % 2.7 % — % 1.8 %

Loss Ratio 62.6 % 58.0 % — % 61.7 % 62.6 % 57.0 % — % 61.7 %

Net policy acquisition costs 14.2 % 19.0 % — % 15.2 % 14.2 % 19.4 % — % 14.9 %

Other operating and general expenses 12.4 % 13.5 % — % 12.6 % 11.9 % 14.6 % — % 12.4 %

Commission and fee income (0.9) % — % — % (0.8) % (0.7) % — % — % (0.5) %

Corporate expenses(1)

— % — % 1.2 % 1.2 % — % — % 1.1 % 1.1 %

Expense ratio 25.7 % 32.5 % 1.2 % 28.2 % 25.4 % 34.0 % 1.1 % 27.9 %

Combined ratio 88.3 % 90.5 % — % 89.9 % 88.0 % 91.0 % — % 89.6 %

Ex-Cat Combined Ratio 86.8 % 87.7 % — % 88.1 % 86.3 % 88.3 % — % 87.8 %

(1) Calculated using consolidated net earned premiums

($ in thousands) Three Months Ended September 30, 2025 Nine Months Ended September 30, 2025

Skyward Specialty Corporate Total Skyward Specialty Corporate Total

Revenues:

Net earned premiums $ 351,797 $ — $ 351,797 $ 947,705 $ — $ 947,705

Commission and fee income 1,904 — 1,904 6,440 — 6,440

Total revenues 353,701 — 353,701 954,145 — 954,145

Expenses:

Losses and loss adjustment expenses 213,780 — 213,780 582,351 — 582,351

Underwriting, acquisition and insurance expenses 98,079 3,597 101,676 263,083 10,740 273,823

Total expenses 311,859 3,597 315,456 845,434 10,740 856,174

Underwriting Income $ 41,842 $ — $ 38,245 $ 108,711 $ — $ 97,971

Combined Ratio

Non-cat loss and LAE

60.2 % — % 60.2 % 60.1 % — % 60.1 %

Cat loss and LAE

0.6 % — % 0.6 % 1.3 % — % 1.3 %

Loss Ratio 60.8 % — % 60.8 % 61.4 % — % 61.4 %

Net policy acquisition costs 13.9 % — % 14.0 % 14.6 % — % 14.6 %

Other operating and general expenses 13.9 % — % 13.9 % 13.2 % — % 13.2 %

Commission and fee income (0.5) % — % (0.5) % (0.7) % — % (0.7) %

Corporate expenses(1)

— % 1.0 % 1.0 % — % 1.1 % 1.1 %

Expense ratio 27.3 % 1.0 % 28.4 % 27.1 % 1.1 % 28.2 %

Combined ratio 88.1 % — % 89.2 % 88.5 % — % 89.6 %

Ex-Cat Combined Ratio 87.5 % — % 88.6 % 87.2 % — % 88.3 %

(1) Calculated using consolidated net earned premiums

The Skyward Specialty segment loss and LAE ratios for the third quarter and first nine months of 2026 increased 1.8 points and 1.2 points, respectively, when compared to the same 2025 periods primarily due to shifts in business mix driven by growth in the accident & health and global agriculture divisions. Both the Skyward Specialty and Apollo segments were impacted by catastrophe losses in the third quarter, predominantly convective storm activity.

The Skyward Group expense ratios for the third quarter and first nine months of 2026 improved when compared to the same 2025 periods. The Skyward Specialty segment’s expense ratios improved 1.6 points and 1.7 points, respectively, when compared to the same 2025 periods, driven by business mix shift, enhanced operating efficiencies, and scale as net earned premiums outpaced expense growth. In the first quarter of 2026, the Company revised its expense presentation to report corporate expenses separately from segment expenses following the closing of the Apollo acquisition. The prior year period has been recast to reflect this change.

Investment Results

Net Investment Income

$ in thousands Three months ended September 30, Nine months ended September 30,

(unaudited) 2026 2025 2026 2025

Short-term investments $ 2,381 $ 3,268 $ 7,338 $ 10,182

Cash and cash equivalents 2,690 695 6,932 2,595

Fixed income

30,338 20,806 87,013 55,358

Alternative & strategic investments

(1,530) (2,755) (9,622) (7,995)

Net investment income

$ 33,879 $ 22,014 $ 91,661 $ 60,140

Net unrealized gains (losses) on securities still held

$ 2,444 $ (8,987) $ 6,146 $ (6,677)

Net realized (losses) gains

(1,978) 16,034 (3,096) 23,564

Net investment gains $ 466 $ 7,047 $ 3,050 $ 16,887

In the first quarter of 2026, the Company revised its presentation of net investment income to (i) report short-term investments separately from cash and cash equivalents following the closing of the Apollo acquisition, and (ii) include equities in alternative & strategic investments after the sale of the majority of the equity portfolio in 2025. The prior year period has been recast to reflect this change.

Net investment income for the third quarter and first nine months of 2026 increased $11.9 million and $31.5 million, respectively, when compared to the same 2025 periods, driven by the addition of the Apollo portfolio, a higher yield, and a larger asset base. The increase in income from cash and cash equivalents was due to an overall increase in the invested asset base from the addition of Apollo when compared to the same 2025 periods.

The alternative & strategic investments portfolio continued to be impacted by the decline in the fair value of limited partnership investments.

Stockholders’ Equity

Stockholders’ equity was $1,276.3 million at September 30, 2026 which represented an increase of 0.7% when compared to stockholders' equity of $1,267.5 million at June 30, 2026. The increase in stockholders’ equity was primarily attributable to net income, partially offset by unrealized losses on available-for-sale investment securities.

Conference Call

At 10:00 a.m. eastern time tomorrow, November 6, 2026, Company management will hold a conference call to discuss quarterly results with insurance industry analysts. Interested parties may listen to the discussion at investors.skywardinsurance.com under Events & Presentations. Additionally, investors can access the earnings call via conference call by registering via the conference link available on our website. Users will receive dial-in information and a unique PIN to join the call upon registering.

Non-GAAP Financial Measures

This release contains certain financial measures and ratios that are not required by, or presented in accordance with, generally accepted accounting principles in the United States (“GAAP”). We refer to these measures as “non-GAAP financial measures.” The non-GAAP financial measures included in this release are operating income, basic and diluted operating earnings per share, annualized operating return on equity, underwriting income, tangible stockholders’ equity, annualized return on tangible equity, annualized operating return on tangible equity, adjusted pro forma gross written premiums and adjusted pro forma fee generating gross written premiums. This release also includes managed premiums, a key management operating metric representing the sum of gross written premiums and fee generating gross written premiums. We use these non-GAAP financial measures when planning, monitoring, and evaluating our performance.

We consider these non-GAAP financial measures to be useful metrics for our management and investors to facilitate operating performance comparisons from period to period. 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 a substitute for revenue or net income, in each case as recognized in accordance with GAAP. In addition, other companies, including companies in our industry, may calculate such measures differently, which reduces their usefulness as comparative measures. For more information regarding these non-GAAP financial measures and a reconciliation of such measures to comparable GAAP financial measures, see the section entitled “Reconciliation of Non-GAAP Financial Measures.”

About Skyward Specialty Insurance Group, Inc.

Skyward Group is the holding company brand for its U.S. and U.K. businesses, Skyward Specialty Insurance Group, Inc.® and Apollo, respectively, delivering a comprehensive suite of specialized insurance solutions across global specialty property and casualty markets. Focused on the specialty industry’s most niche, complex risks of today and the emerging challenges of tomorrow, Skyward Group leverages the forward-looking insight and disciplined execution of each organization to drive sustainable growth and long-term value for its shareholders, distribution partners, and other stakeholders.

For more information about Skyward Group, Skyward Specialty and Apollo, please visit skywardgroup.com.

Forward-Looking Statements

Except for historical information, this news release and statements made on the related conference call, contain consists of forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. The forward-looking statements are typically, but not always, identified through use of the words “believe,” “expect,” “enable,” “may,” “will,” “could,” “intends,” “estimate,” “anticipate,” “plan,” “predict,” “probable,” “potential,” “positioned,” “possible,” “should,” “continue,” and other words of similar meaning. These forward-looking statements are subject to risks and uncertainties that could cause actual results to differ materially from those projected, anticipated or implied. The most significant of these uncertainties are described in Skyward Group's most recent Annual Report on Form 10-K and Quarterly Reports on Form 10-Q filed with the Securities and Exchange Commission, and include (but are not limited to) legislative and regulatory changes in the U.S. at both the state and federal level and in the U.K., class action litigation involving the insurance industry and judicial decisions affecting claims, policy coverages and the general costs of doing business, the potential loss of key members of our management team or key employees and our ability to attract and retain personnel, the impact of competition on products and pricing, inflation in the costs of the products and services insurance pays for, product development, geographic spread of risk, weather and weather-related events, other types of catastrophic events, our ability to obtain reinsurance coverage at prices and on terms that allow us to transfer risk and adequately protect our company against financial loss, losses resulting from reinsurance counterparties failing to pay us on reinsurance claims, our ability to successfully integrate Apollo and realize the anticipated benefits of the acquisition, risks related to our Lloyd’s operations, including changes in syndicate participations and Lloyd’s regulatory requirements, changes in interest rates, credit markets and the value of our investment portfolio, and fluctuations in foreign currency exchange rate. These forward-looking statements speak only as of the date of this 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.

Skyward Specialty Insurance Group, Inc.

Investor Contact

Jordan Arnold

Skyward Specialty Insurance Group

346-215-0250

jarnold@skywardinsurance.com

Media Contact

Haley Doughty

Skyward Specialty Insurance Group

713-935-4944

hdoughty@skywardinsurance.com

Skyward Specialty Insurance Group, Inc.

Consolidated Balance Sheets

($ in thousands, except share and per share amounts)

(unaudited) September 30,

2026 December 31, 2025

Assets

Investments:

Fixed maturity securities, available-for-sale, at fair value (net of allowance for credit losses of $5,910 and $7,000, respectively) (amortized cost of $2,265,283 and $1,848,755, respectively) $ 2,191,576 $ 1,856,303

Fixed maturity securities, held-to-maturity, at amortized cost (net of allowance for credit losses of $4,228 and $468, respectively) 26,446 32,822

Equity securities, at fair value 1,088 1,174

Mortgage loans, at fair value 6,712 9,902

Equity method investments 62,686 77,365

Other long-term investments 66,847 58,650

Short-term investments, at fair value 531,449 264,299

Total investments 2,886,804 2,300,515

Cash and cash equivalents 187,615 168,544

Restricted cash 96,675 30,570

Funds at Lloyd’s 121,630 2,509

Options, at fair value 31,846 34,857

Premiums and commissions receivable, net 1,091,077 544,217

Reinsurance recoverables, net 1,460,189 1,119,880

Ceded unearned premium 389,749 238,948

Deferred policy acquisition costs and VOBA 190,373 136,100

Deferred tax assets 65,773 27,865

Goodwill and intangible assets, net 469,054 88,040

Other assets 155,661 99,807

Total assets $ 7,146,446 $ 4,791,852

Liabilities and stockholders’ equity

Liabilities:

Reserves for losses and loss adjustment expenses $ 3,208,137 $ 2,318,894

Unearned premiums 1,225,726 774,035

Deferred ceding commission 62,708 46,453

Reinsurance and premium payables 565,980 279,888

Funds held for others 151,163 128,003

Deferred tax liabilities 66,924 —

Accounts payable and accrued liabilities 152,910 115,034

Notes payable 417,037 100,411

Subordinated debt, net of debt issuance costs 19,593 19,569

Total liabilities 5,870,178 3,782,287

Stockholders’ equity

Common stock, $0.01 par value, 500,000,000 shares authorized, 44,846,532 shares issued and 44,413,449 shares outstanding at September 30, 2026; 40,511,222 shares issued and outstanding at December 31, 2025

448 405

Treasury stock, at cost, 433,083 and 0 shares, respectively

(19,552) —

Additional paid-in capital 933,877 730,555

Accumulated other comprehensive (loss) income (54,218) 11,457

Retained earnings 415,713 267,148

Total stockholders’ equity 1,276,268 1,009,565

Total liabilities and stockholders’ equity $ 7,146,446 $ 4,791,852

Skyward Specialty Insurance Group, Inc.

Condensed Consolidated Statements of Operations and Comprehensive Income

($ in thousands) Three months ended September 30, Nine months ended September 30,

(unaudited) 2026 2025 2026 2025

Revenues:

Net earned premiums

406,864

351,797

$ 1,285,343 $ 947,705

Underwriting fee income 11,000 — 33,666 —

Commission and fee income 3,118 1,904 6,979 6,440

Net investment income 33,879 22,014 91,661 60,140

Net investment gains 466 7,047 3,050 16,887

Other income (loss) 14 (236) 42 (216)

Total revenues 455,341 382,526 1,420,741 1,030,956

Expenses:

Losses and loss adjustment expenses 251,036 213,780 793,000 582,351

Underwriting, acquisition and insurance expenses 118,002 101,676 365,897 273,823

Fee‑based service expenses 4,075 — 12,807 —

Interest expense 6,997 1,919 23,528 5,629

Amortization expense 8,843 455 26,529 1,164

Other expenses 2,744 4,149 9,703 6,212

Total expenses 391,697 321,979 1,231,464 869,179

Income before income taxes 63,644 60,547 189,277 161,777

Income tax expense 13,848 14,646 40,712 34,979

Net income $ 49,796 $ 45,901 $ 148,565 $ 126,798

Comprehensive income:

Net income $ 49,796 $ 45,901 $ 148,565 $ 126,798

Other comprehensive (loss) income:

Unrealized gains and losses on investments:

Net change in unrealized (losses) gains on investments, net of tax (47,742) 6,740 (65,584) 30,000

Reclassification adjustment for gains on securities no longer held, net of tax 849 5,465 861 1,659

Foreign currency translation adjustment (234) — (952) —

Total other comprehensive (loss) income (47,127) 12,205 (65,675) 31,659

Comprehensive income $ 2,669 $ 58,106 $ 82,890 $ 158,457

Skyward Specialty Insurance Group, Inc.

Share and Per Share Data

($ in thousands, except share and per share amounts) Three months ended September 30, Nine months ended September 30,

(unaudited) 2026 2025 2026 2025

Weighted average basic shares 44,405,132 40,487,069 44,462,989 40,377,864

Weighted average diluted shares 45,799,617 41,868,449 45,618,514 41,784,976

Basic earnings per share $ 1.12 $ 1.13 $ 3.34 $ 3.14

Diluted earnings per share $ 1.09 $ 1.10 $ 3.26 $ 3.03

Basic operating earnings per share $ 1.32 $ 1.09 $ 3.93 $ 2.94

Diluted operating earnings per share $ 1.28 $ 1.05 $ 3.83 $ 2.84

Annualized ROE (1)

15.7 % 19.7 % 17.3 % 19.3 %

Annualized operating ROE (2)

18.4 % 19.0 % 20.4 % 18.2 %

Annualized ROTE (3)

23.0 % 21.8 % 22.1 % 21.4 %

Annualized operating ROTE (4)

27.0 % 21.0 % 25.9 % 20.2 %

September 30, December 31,

2026 2025

Shares outstanding 44,413,449 40,511,222

Fully diluted shares outstanding 46,573,658 42,292,371

Book value per share $ 28.74 $ 24.92

Fully diluted book value per share $ 27.40 $ 23.87

(1) Annualized ROE is net income expressed on an annualized basis as a percentage of average beginning and ending stockholders' equity during the period.

(2) Annualized operating ROE is operating income expressed on an annualized basis as a percentage of average beginning and ending stockholders' equity during the period.

(3) Annualized ROTE is net income expressed on an annualized basis as a percentage of average beginning and ending tangible stockholders' equity during the period.

(4) Annualized operating ROTE is operating income expressed on an annualized basis as a percentage of average beginning and ending tangible stockholders' equity during the period.

Skyward Specialty Insurance Group, Inc.

Reconciliation of Non-GAAP Financial Measures

Operating income – We define operating income as net income excluding the impact of certain items that may not be indicative of underlying business trends, operating results, or future outlook, net of tax impact. We use operating income as an internal performance measure in the management of our operations because we believe it gives our management and other users of our financial information useful insight into our results of operations and our underlying business performance. Operating income should not be viewed as a substitute for net income calculated in accordance with GAAP, and other companies may define operating income differently.

($ in thousands) Three months ended September 30, Nine months ended September 30,

(unaudited) 2026 2025 2026 2025

Pre-tax After-tax Pre-tax After-tax Pre-tax After-tax Pre-tax After-tax

Income as reported $ 63,644 $ 49,796 $ 60,547 $ 45,901 $ 189,277 $ 148,565 $ 161,777 $ 126,798

Less (add):

Net investment gains 466 365 7,047 5,342 3,050 2,394 16,887 13,236

Amortization expense (8,843) (6,919) (455) (345) (26,529) (20,823) (1,164) (912)

Other income (loss) 14 11 (236) (179) 42 33 (216) (169)

Other expenses (2,744) (2,147) (4,149) (3,145) (9,703) (7,616) (6,212) (4,869)

Operating income $ 74,751 $ 58,486 $ 58,340 $ 44,228 $ 222,417 $ 174,577 $ 152,482 $ 119,512

Underwriting income – We define underwriting income as net income before income taxes excluding net investment income, net realized and unrealized gains and losses on investments, impairment charges, interest expense, amortization expense and other income and expenses. Underwriting income represents the pre-tax profitability of our underwriting operations and allows us to evaluate our underwriting performance without regard to investment income. We use this metric as we believe it gives our management and other users of our financial information useful insight into our underlying business performance. Underwriting income should not be viewed as a substitute for pre-tax income calculated in accordance with GAAP, and other companies may define underwriting income differently.

($ in thousands) Three months ended September 30, Nine months ended September 30,

(unaudited) 2026 2025 2026 2025

Income before income taxes $ 63,644 $ 60,547 $ 189,277 $ 161,777

Add:

Interest expense 6,997 1,919 23,528 5,629

Amortization expense 8,843 455 26,529 1,164

Other expenses 2,744 4,149 9,703 6,212

Less:

Net investment income 33,879 22,014 91,661 60,140

Net investment gains 466 7,047 3,050 16,887

Other income 14 (236) 42 (216)

Underwriting income $ 47,869 $ 38,245 $ 154,284 $ 97,971

Skyward Specialty Insurance Group, Inc.

Reconciliation of Non-GAAP Financial Measures

Tangible Stockholders’ Equity – We define tangible stockholders’ equity as stockholders’ equity excluding goodwill and intangible assets and the related deferred tax impact. Our definition of tangible stockholders’ equity may not be comparable to that of other companies and should not be viewed as a substitute for stockholders’ equity calculated in accordance with GAAP. We use tangible stockholders’ equity internally to evaluate the strength of our balance sheet and to compare returns relative to this measure.

($ in thousands) September 30, December 31,

(unaudited) 2026 2025 2025

Stockholders’ equity

$ 1,276,268 $ 961,423 $ 1,009,565

Less: Goodwill and intangible assets 469,054 88,417 88,040

Add: Deferred tax impact 65,500 — —

Tangible stockholders’ equity

$ 872,714 $ 873,006 $ 921,525

Adjusted pro forma gross written premiums – We define adjusted pro forma gross written premiums as pro forma gross written premiums adjusted for the impact of changes in Apollo syndicate participation. We use this measure to evaluate premium growth trends on a consistent participation basis across periods. Adjusted pro forma gross written premiums is a non-GAAP financial measure and should not be considered a substitute for gross written premiums calculated in accordance with GAAP.

$ in thousands Three months ended September 30, 2025

Syndicate 1969 Syndicate 1971 Total Apollo Segment Total Skyward Group

Pro forma gross written premiums $ 73,525 $ 57,449 $ 130,974 $ 737,483

Impact of the change in participations (12,420) 12,225 (195) (195)

Adjusted pro forma gross written premiums

$ 61,105 $ 69,674 $ 130,779 $ 737,288

$ in thousands Nine months ended September 30, 2025

Syndicate 1969 Syndicate 1971 Total Apollo Segment Total Skyward Group

Pro forma gross written premiums $ 192,828 $ 86,727 $ 279,555 $ 2,006,304

Impact of the change in participations (32,664) 12,079 (20,585) (20,585)

Adjusted pro forma gross written premiums

$ 160,164 $ 98,806 $ 258,970 $ 1,985,719

Adjusted pro forma fee generating gross written premiums – We define adjusted pro forma fee generating gross written premiums as pro forma fee generating gross written premiums adjusted for the impact of changes in Apollo syndicate participation percentages. We believe this measure provides a more meaningful comparison of fee generating business on a consistent participation basis across periods. Adjusted pro forma fee generating gross written premiums is a non-GAAP financial measure and may not be comparable to similarly titled measures used by other companies.

$ in thousands Three months ended September 30, 2025

Aligned Syndicates Partner Syndicates Total

Pro forma fee generating gross written premiums $ 369,353 $ 67,355 $ 436,708

Impact of the change in participations 195 N/A 195

Adjusted pro forma fee generating gross written premiums

$ 369,548 $ 67,355 $ 436,903

Skyward Specialty Insurance Group, Inc.

Reconciliation of Non-GAAP Financial Measures

$ in thousands Nine months ended September 30, 2025

Aligned Syndicates Partner Syndicates Total

Pro forma fee generating gross written premiums $ 696,593 $ 181,528 $ 878,121

Impact of the change in participation(s) 20,585 N/A 20,585

Adjusted pro forma fee generating gross written premiums

$ 717,178 $ 181,528 $ 898,706

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