Form 8-K

8-K — Skyward Specialty Insurance Group, Inc.

Accession: 0001519449-26-000047

Filed: 2026-08-04

Period: 2026-08-04

CIK: 0001519449

SIC: 6331 (FIRE, MARINE & CASUALTY INSURANCE)

Item: Results of Operations and Financial Condition

Item: Financial Statements and Exhibits

Documents

8-K — skwd-20260804.htm (Primary)

EX-99.1 (earningsrelease-ex9912q2026.htm)

GRAPHIC (picture2.jpg)

XML — IDEA: XBRL DOCUMENT (R1.htm)

8-K

8-K (Primary)

Filename: skwd-20260804.htm · Sequence: 1

skwd-20260804

false000151944900015194492026-08-042026-08-04

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): August 4, 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 August 4, 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 June 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 August 4, 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:

August 4, 2026

/s/ Mark Haushill

Mark Haushill

Chief Financial Officer

EX-99.1

Filename: earningsrelease-ex9912q2026.htm · Sequence: 2

Document

Exhibit 99.1

Skyward Group Reports Second Quarter 2026 Results

Houston, TX – August 4, 2026 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Group” or the “Company”) today reported second quarter 2026 results.

Summary Financial Data

($ in thousands, except per share amounts) Three months ended June 30, Six months ended June 30,

unaudited 2026

2025(1)

2026

2025(1)

Managed Premiums $ 1,058,675 $ 900,849 $ 2,026,384 $ 1,710,234

Gross written premiums(2)

$ 740,554 $ 653,861 $ 1,408,258 $ 1,248,431

Fee generating gross written premiums(2)

$ 318,121 $ 246,988 $ 618,126 $ 461,803

Net written premiums $ 485,616 $ 339,213 $ 918,499 $ 682,484

Net income $ 49,038 $ 38,839 $ 98,769 $ 80,897

Net operating income(3)

$ 59,198 $ 37,496 $ 116,091 $ 75,233

Basic earnings per share $ 1.10 $ 0.96 $ 2.22 $ 2.01

Diluted operating earnings per share $ 1.30 $ 0.89 $ 2.55 $ 1.78

Annualized ROE (4)

15.7 % 17.7 % 17.3 % 19.1 %

Annualized operating ROE (5)

19.0 % 17.1 % 20.4 % 17.8 %

(1) Select second 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 second quarter included:

•Managed premiums increased 17.5%(2) compared to 2025;

•Gross written premiums increased 13.3%(1)(2) compared to 2025;

•Combined ratio of 89.5%;

•Ex-Cat combined ratio of 87.6%;

•Repurchased 223 thousand shares of common stock for $9.7 million and expanded the share repurchase authorization from $50 million to $100 million;

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

•Book value per share of $28.55, an increase of 14.6% compared to December 31, 2025.

Skyward Group Chairman and CEO Andrew Robinson commented, “We delivered another quarter of excellent results reflecting the strength, resilience and earnings power of our Rule Our Niche strategy, our uniquely diversified business portfolio, and disciplined execution. Diluted operating earnings per share of $1.30 increased 46% year over year, and our annualized operating return on equity of 20.4% for the first half of the year underscores our continued strong returns and outstanding earnings growth. Our combined ratio of 89.5%, inclusive of 1.9 points of catastrophe losses, again demonstrates the quality of our underwriting and disciplined risk management. Gross written premiums grew 13% and fee generating premiums grew 29% to $318 million in the quarter. Book value per share increased to $28.55 during the quarter. We believe we are exceptionally well positioned to continue to deliver top quartile results and long-term value for shareholders.”

Results of Operations

Gross Written Premiums By Underwriting Division

($ in thousands) Three months ended June 30, Six months ended June 30,

2026 2025 %

Change 2026 2025 % Change

Skyward Specialty Segment

Accident & Health $ 95,456 $ 60,489 57.8 % $ 187,465 $ 123,658 51.6 %

Captives 64,251 76,994 (16.6) % 122,165 143,923 (15.1) %

Credit & Surety 63,759 55,131 15.6 % 127,933 100,159 27.7 %

Energy Solutions 62,690 74,822 (16.2) % 111,556 150,416 (25.8) %

Global Agriculture 111,939 57,179 95.8 % 214,291 137,796 55.5 %

Global Property 71,109 83,992 (15.3) % 105,626 130,678 (19.2) %

Professional Lines 34,978 37,555 (6.9) % 71,206 77,772 (8.4) %

Specialty Programs 111,441 85,955 29.7 % 206,208 148,630 38.7 %

Transactional E&S 52,296 53,461 (2.2) % 102,360 105,467 (2.9) %

Total continuing business $ 667,919 $ 585,578 14.1 % $ 1,248,810 $ 1,118,499 11.7 %

Exited business (146) (664) (78.0) % 767 1,741 (55.9) %

Total Skyward Specialty Segment gross written premiums $ 667,773 $ 584,914 14.2 % $ 1,249,577 $ 1,120,240 11.5 %

Apollo Segment(1)(2)

Syndicate 1969 59,431 55,207 7.7 % 124,439 99,059 25.6 %

Syndicate 1971 13,350 13,740 (2.8) % 34,242 29,132 17.5 %

Total Apollo Segment gross written premiums 72,781 68,947 5.6 % 158,681 128,191 23.8 %

Total gross written premiums(1)(2)

$ 740,554 $ 653,861 13.3 % $ 1,408,258 $ 1,248,431 12.8 %

(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”.

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. Apollo receives managing agency fees and performance‑based income for their managing agency services from all syndicates on its Lloyd's platform.

($ in thousands) Three months ended June 30, Six months ended June 30,

2026 2025 % Change 2026 2025 % Change

Total gross written premiums(1)(2)

$ 740,554 $ 653,861 13.3% $ 1,408,258 $ 1,248,431 12.8%

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

Aligned Syndicates 217,196 191,527 13.4% 427,745 347,630 23.0%

Partner Syndicates 100,925 55,461 82.0% 190,381 114,173 66.7%

Total fee generating gross written premiums $ 318,121 $ 246,988 28.8% $ 618,126 $ 461,803 33.9%

Total Skyward Group managed premiums $ 1,058,675 $ 900,849 17.5% $ 2,026,384 $ 1,710,234 18.5%

(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”.

Underwriting Results

($ in thousands) Three Months Ended June 30, 2026 Six Months Ended June 30, 2026

Skyward Specialty Apollo Corporate Total Skyward Specialty Apollo Corporate Total

Revenues:

Net earned premiums $ 378,346 $ 66,126 $ — $ 444,472 $ 742,289 $ 136,190 $ — $ 878,479

Underwriting fee income — 12,588 — 12,588 — 22,666 — 22,666

Commission and fee income 2,334 — — 2,334 3,861 — — 3,861

Total revenues 380,680 78,714 — 459,394 746,150 158,856 — 905,006

Expenses:

Losses and loss adjustment expenses 236,967 39,774 — 276,741 465,198 76,766 — 541,964

Underwriting, acquisition and insurance expenses 94,131 24,778 4,372 123,281 191,094 47,520 9,281 247,895

Fee‑based service expenses — 4,562 — 4,562 — 8,732 — 8,732

Total expenses 331,098 69,114 4,372 404,584 656,292 133,018 9,281 798,591

Underwriting Income $ 49,582 $ 9,600 $ — $ 54,810 $ 89,858 $ 25,838 $ — $ 106,415

Combined Ratio

Non-cat loss and LAE

61.3 % 54.7 % — % 60.4 % 61.0 % 53.8 % — % 59.8 %

Cat loss and LAE

1.3 % 5.4 % — % 1.9 % 1.7 % 2.6 % — % 1.9 %

Loss Ratio 62.6 % 60.1 % — % 62.3 % 62.7 % 56.4 % — % 61.7 %

Net policy acquisition costs 14.0 % 27.6 % — % 16.0 % 14.0 % 19.7 % — % 14.8 %

Other operating and general expenses 10.9 % 9.9 % — % 10.7 % 11.7 % 15.2 % — % 12.3 %

Commission and fee income (0.6) % — % — % (0.5) % (0.5) % — % — % (0.4) %

Corporate expenses(1)

— % — % 1.0 % 1.0 % — % — % 1.1 % 1.1 %

Expense ratio 24.3 % 37.5 % 1.0 % 27.2 % 25.2 % 34.9 % 1.1 % 27.8 %

Combined ratio 86.9 % 97.6 % — % 89.5 % 87.9 % 91.3 % — % 89.5 %

Ex-Cat Combined Ratio 85.6 % 92.2 % — % 87.6 % 86.2 % 88.7 % — % 87.6 %

(1) Calculated using consolidated net earned premiums

($ in thousands) Three Months Ended June 30, 2025 Six Months Ended June 30, 2025

Skyward Specialty Corporate Total Skyward Specialty Corporate Total

Revenues:

Net earned premiums $ 295,542 $ —

$ 295,542 $ 595,908 $ — $ 595,908

Commission and fee income 2,560 — 2,560 4,536 — 4,536

Total revenues 298,102 — 298,102 600,444 — 600,444

Expenses:

Losses and loss adjustment expenses 181,262 — 181,262 368,571 — 368,571

Underwriting, acquisition and insurance expenses 82,366 3,230 85,596 165,004 7,143 172,147

Total expenses 263,628 3,230 266,858 533,575 7,143 547,200

Underwriting Income $ 34,474 $ —

$ 31,244 $ 66,869 $ — $ 59,726

Combined Ratio

Non-cat loss and LAE

59.9 % — % 59.9 % 60.1 % — % 60.1 %

Cat loss and LAE

1.4 % — % 1.4 % 1.8 % — % 1.8 %

Loss Ratio 61.3 % — % 61.3 % 61.9 % — % 61.9 %

Net policy acquisition costs 15.1 % — % 15.1 % 15.0 % — % 15.0 %

Other operating and general expenses 12.8 % — % 12.8 % 12.7 % — % 12.7 %

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

Corporate expenses(1)

— % 1.1 % 1.1 % — % 1.2 % 1.2 %

Expense ratio 27.0 % 1.1 % 28.1 % 26.9 % 1.2 % 28.1 %

Combined ratio 88.3 % — % 89.4 % 88.8 % — % 90.0 %

Ex-Cat Combined Ratio 86.9 % — % 88.0 % 87.0 % — % 88.2 %

(1) Calculated using consolidated net earned premiums

The Skyward Specialty segment loss and LAE ratios for the second quarter and first half of 2026 increased 1.3 points and 0.8 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. The Apollo segment loss and LAE ratios for the second quarter and first half of 2026 were impacted by catastrophe losses, primarily from the conflict in the Middle East.

The expense ratios for the second quarter and first half of 2026 improved 0.9 points and 0.3 points, respectively, when compared to the same 2025 periods. The Skyward Specialty segment’s expense ratio improved 2.7 points and 1.7 points, respectively, when compared to the same 2025 periods, primarily driven by business mix shift, enhanced operating efficiencies, and scale benefits 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 June 30, Six months ended June 30,

(unaudited) 2026 2025 2026 2025

Short-term investments $ 2,469 $ 3,713 $ 4,957 $ 6,914

Cash and cash equivalents 2,583 976 4,242 1,900

Fixed income

29,310 17,822 56,675 34,552

Alternative & strategic investments

(3,635) (3,807) (8,092) (5,240)

Net investment income

$ 30,727 $ 18,704 $ 57,782 $ 38,126

Net unrealized gains (losses) on securities still held

$ 1,927 $ (3,181) $ 3,702 $ 2,310

Net realized (losses) gains

(2,528) 6,271 (1,118) 7,530

Net investment (losses) gains $ (601) $ 3,090 $ 2,584 $ 9,840

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 second quarter and first half of 2026 increased $12.0 million and $19.7 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 $1,267.5 million at June 30, 2026 which represented an increase of 3.5% when compared to stockholders' equity of $1,224.9 million at March 31, 2026. The increase in stockholders’ equity was primarily attributable to net income, partially offset by repurchases of the Company’s common stock.

Conference Call

At 9:00 a.m. eastern time tomorrow, August 5, 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. 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.” 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, all other information in this news release 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,” “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 Form 10-K, and include (but are not limited to) legislative changes at both the state and federal level, state and federal regulatory rule making promulgations and adjudications, 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, and losses resulting from reinsurance counterparties failing to pay us on reinsurance claims. 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) June 30,

2026 December 31, 2025

Assets

Investments:

Fixed maturity securities, available-for-sale, at fair value (net of allowance for credit losses of $6,228 and $7,000, respectively) (amortized cost of $2,206,626 and $1,848,755, respectively) $ 2,192,183 $ 1,856,303

Fixed maturity securities, held-to-maturity, at amortized cost (net of allowance for credit losses of $2,256 and $468, respectively) 28,192 32,822

Equity securities, at fair value 1,141 1,174

Mortgage loans, at fair value 9,218 9,902

Equity method investments 62,725 77,365

Other long-term investments 52,295 58,650

Short-term investments, at fair value 392,634 264,299

Total investments 2,738,388 2,300,515

Cash and cash equivalents 219,221 168,544

Restricted cash 83,302 30,570

Funds at Lloyd’s 121,630 2,509

Options, at fair value 40,535 34,857

Premiums and commissions receivable, net 978,409 544,217

Reinsurance recoverables, net 1,411,648 1,119,880

Ceded unearned premium 337,180 238,948

Deferred policy acquisition costs and VOBA 186,491 136,100

Deferred tax assets 47,987 27,865

Goodwill and intangible assets, net 471,185 88,040

Other assets 145,163 99,807

Total assets $ 6,781,139 $ 4,791,852

Liabilities and stockholders’ equity

Liabilities:

Reserves for losses and loss adjustment expenses $ 3,070,598 $ 2,318,894

Unearned premiums 1,078,246 774,035

Deferred ceding commission 54,466 46,453

Reinsurance and premium payables 509,081 279,888

Funds held for others 169,051 128,003

Deferred tax liabilities 67,801 —

Accounts payable and accrued liabilities 127,154 115,034

Notes payable 417,620 100,411

Subordinated debt, net of debt issuance costs 19,585 19,569

Total liabilities 5,513,602 3,782,287

Stockholders’ equity

Common stock, $0.01 par value, 500,000,000 shares authorized, 44,827,499 shares issued and 44,396,493 shares outstanding at June 30, 2026; 40,511,222 shares issued and outstanding at December 31, 2025

448 405

Treasury stock, at cost, 431,006 and 0 shares, respectively

(19,427) —

Additional paid-in capital 927,690 730,555

Accumulated other comprehensive (loss) income (7,091) 11,457

Retained earnings 365,917 267,148

Total stockholders’ equity 1,267,537 1,009,565

Total liabilities and stockholders’ equity $ 6,781,139 $ 4,791,852

Skyward Specialty Insurance Group, Inc.

Condensed Consolidated Statements of Operations and Comprehensive Income

($ in thousands) Three months ended June 30, Six months ended June 30,

(unaudited) 2026 2025 2026 2025

Revenues:

Net earned premiums

444,472

295,542

$ 878,479 $ 595,908

Underwriting fee income 12,588 — 22,666 —

Commission and fee income 2,334 2,560 3,861 4,536

Net investment income 30,727 18,704 57,782 38,126

Net investment (losses) gains (601) 3,090 2,584 9,840

Other income 13 7 28 20

Total revenues 489,533 319,903 965,400 648,430

Expenses:

Losses and loss adjustment expenses 276,741 181,262 541,964 368,571

Underwriting, acquisition and insurance expenses 123,281 85,596 247,895 172,147

Fee‑based service expenses 4,562 — 8,732 —

Interest expense 8,812 1,876 16,531 3,710

Amortization expense 8,843 372 17,686 709

Other expenses 3,737 1,002 6,959 2,063

Total expenses 425,976 270,108 839,767 547,200

Income before income taxes 63,557 49,795 125,633 101,230

Income tax expense 14,519 10,956 26,864 20,333

Net income $ 49,038 $ 38,839 $ 98,769 $ 80,897

Comprehensive income:

Net income $ 49,038 $ 38,839 $ 98,769 $ 80,897

Other comprehensive income:

Unrealized gains and losses on investments:

Net change in unrealized (losses) gains on investments, net of tax (625) 11,005 (17,842) 23,260

Reclassification adjustment for (losses) gains on securities no longer held, net of tax (490) (3,624) 12 (3,806)

Foreign currency translation adjustment 150 — (718) —

Total other comprehensive (loss) income (965) 7,381 (18,548) 19,454

Comprehensive income $ 48,073 $ 46,220 $ 80,221 $ 100,351

Skyward Specialty Insurance Group, Inc.

Share and Per Share Data

($ in thousands, except share and per share amounts) Three months ended June 30, Six months ended June 30,

(unaudited) 2026 2025 2026 2025

Weighted average basic shares 44,521,162 40,445,391 44,492,608 40,322,051

Weighted average diluted shares 45,692,641 41,871,496 45,526,233 41,771,215

Basic earnings per share $ 1.10 $ 0.96 $ 2.22 $ 2.01

Diluted earnings per share $ 1.07 $ 0.93 $ 2.17 $ 1.94

Basic operating earnings per share $ 1.33 $ 0.92 $ 2.61 $ 1.85

Diluted operating earnings per share $ 1.30 $ 0.89 $ 2.55 $ 1.78

Annualized ROE (1)

15.7 % 17.7 % 17.3 % 19.1 %

Annualized operating ROE (2)

19.0 % 17.1 % 20.4 % 17.8 %

Annualized ROTE (3)

23.4 % 19.7 % 22.2 % 21.3 %

Annualized operating ROTE (4)

28.2 % 19.0 % 26.0 % 19.8 %

June 30, December 31,

2026 2025

Shares outstanding 44,396,493 40,511,222

Fully diluted shares outstanding 46,605,142 42,292,371

Book value per share $ 28.55 $ 24.92

Fully diluted book value per share $ 27.20 $ 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 June 30, Six months ended June 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 $ 63,557 $ 49,038 $ 49,795 $ 38,839 $ 125,633 $ 98,769 $ 101,230 $ 80,897

Less (add):

Net investment (losses) gains (601) (464) 3,090 2,410 2,584 2,031 9,840 7,864

Amortization expense (8,843) (6,823) (372) (290) (17,686) (13,904) (709) (567)

Other income 13 10 7 5 28 22 20 16

Other expenses (3,737) (2,883) (1,002) (782) (6,959) (5,471) (2,063) (1,649)

Operating income $ 76,725 $ 59,198 $ 48,072 $ 37,496 $ 147,666 $ 116,091 $ 94,142 $ 75,233

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 June 30, Six months ended June 30,

(unaudited) 2026 2025 2026 2025

Income before income taxes $ 63,557 $ 49,795 $ 125,633 $ 101,230

Add:

Interest expense 8,812 1,876 16,531 3,710

Amortization expense 8,843 372 17,686 709

Other expenses 3,737 1,002 6,959 2,063

Less:

Net investment income 30,727 18,704 57,782 38,126

Net investment (losses) gains (601) 3,090 2,584 9,840

Other income 13 7 28 20

Underwriting income $ 54,810 $ 31,244 $ 106,415 $ 59,726

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) June 30, December 31,

(unaudited) 2026 2025 2025

Stockholders’ equity

$ 1,267,537 $ 899,915 $ 1,009,565

Less: Goodwill and intangible assets 471,185 88,795 88,040

Add: Deferred tax impact 65,500 — —

Tangible stockholders’ equity

$ 861,852 $ 811,120 $ 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 June 30, 2025

Syndicate 1969 Syndicate 1971 Total Apollo Segment Total Skyward Group

Pro forma gross written premiums $ 65,854 $ 10,337 $ 76,191 $ 661,105

Impact of the change in participations (10,647) 3,403 (7,244) (7,244)

Adjusted pro forma gross written premiums

$ 55,207 $ 13,740 $ 68,947 $ 653,861

$ in thousands Six months ended June 30, 2025

Syndicate 1969 Syndicate 1971 Total Apollo Segment Total Skyward Group

Pro forma gross written premiums $ 119,303 $ 29,278 $ 148,581 $ 1,268,821

Impact of the change in participations (20,244) (146) (20,390) (20,390)

Adjusted pro forma gross written premiums

$ 99,059 $ 29,132 $ 128,191 $ 1,248,431

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 June 30, 2025

Aligned Syndicates Partner Syndicates Total

Pro forma fee generating gross written premiums $ 184,283 $ 55,461 $ 239,744

Impact of the change in participations 7,244 N/A 7,244

Adjusted pro forma fee generating gross written premiums

$ 191,527 $ 55,461 $ 246,988

Skyward Specialty Insurance Group, Inc.

Reconciliation of Non-GAAP Financial Measures

$ in thousands Six months ended June 30, 2025

Aligned Syndicates Partner Syndicates Total

Pro forma fee generating gross written premiums $ 327,240 $ 114,173 $ 441,413

Impact of the change in participation(s) 20,390 N/A 20,390

Adjusted pro forma fee generating gross written premiums

$ 347,630 $ 114,173 $ 461,803

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