What changed in this filing

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Item 1. Financial Statements

2026-05-11 compared with 2025-11-06 · 458 added, 350 removed, 608 unchanged (57% of the section changed)

3 unchanged sentences

CONDENSED CONSOLIDATED BALANCE SHEETS (UNAUDITED)

September 30, 2025 December 31, 2024

March 31, 2026 December 31, 2025

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

11 unchanged sentences

Restricted cash 60,521 30,570

Premiums receivable, net 583,148 321,641

Funds at Lloyd’s 108,846 2,509

Options, at fair value 24,401 34,857

Premiums and commissions receivable, net 830,509 544,217

Reinsurance recoverables, net 1,336,937 1,119,880

Ceded unearned premium 314,850 238,948

Deferred policy acquisition costs 144,932 113,183

Deferred income taxes 28,022 30,486

Deferred policy acquisition costs and VOBA 193,703 136,100

Deferred tax assets 44,138 27,865

Goodwill and intangible assets, net 473,316 88,040

7 unchanged sentences

Funds held for others 157,380 128,003

Deferred tax liabilities 68,466 —

Accounts payable and accrued liabilities 148,737 115,034

3 unchanged sentences

Stockholders’ equity

Common stock, $ 0.01 par value, 500,000,000 shares authorized, 40,487,365 and 40,127,908 shares issued and outstanding, respectively

Common stock, $ 0.01 par value, 500,000,000 shares authorized, 44,728,087 shares issued and 44,543,065 shares outstanding at March 31, 2026;

40,511,222 shares issued and outstanding at December 31, 2025

Treasury stock, at cost, 185,022 and 0 shares, respectively

Additional paid-in capital 922,311 730,555

Accumulated other comprehensive income (loss) 9,539 ( 22,120 )

Accumulated other comprehensive (loss) income ( 6,126 ) 11,457

Retained earnings 316,879 267,148

6 unchanged sentences

AND COMPREHENSIVE INCOME (UNAUDITED)

Three months ended September 30, Nine months ended September 30,

Three months ended March 31,

($ in thousands, except share and per share amounts) 2026 2025

Net earned premiums $ 434,007 $ 300,366

Underwriting fee income 10,078 —

Commission and fee income 1,527 1,976

1 unchanged sentence

Net investment gains 3,185 6,750

Other loss ( 236 ) ( 195 ) ( 216 ) ( 202 )

Other income 15 13

Total revenues 475,867 328,527

1 unchanged sentence

Underwriting, acquisition and insurance expenses 124,614 86,551

Fee‑based service expenses 4,170 —

Interest expense 7,719 1,834

7 unchanged sentences

Net income $ 49,731 $ 42,058

Other comprehensive income:

Other comprehensive (loss) income:

Unrealized gains and losses on investments:

Net change in unrealized gains on investments, net of tax 6,740 31,396 30,000 24,527

Net change in unrealized (losses) gains on investments, net of tax ( 17,217 ) 12,255

Reclassification adjustment for gains (losses) on securities no longer held, net of tax 502 ( 182 )

Total other comprehensive income 12,205 29,433 31,659 21,250

Foreign currency translation adjustment ( 868 ) —

Total other comprehensive (loss) income ( 17,583 ) 12,073

Comprehensive income $ 32,148 $ 54,131

9 unchanged sentences

CONDENSED CONSOLIDATED STATEMENTS OF STOCKHOLDERS’ EQUITY (UNAUDITED)

Three months ended September 30,

($ in thousands, except share amounts) 2025 2024

Common shares:

Balance at beginning of period 40,486,656 40,096,132

Issuance of shares 709 3,799

Balance at September 30 40,487,365 40,099,931

Common stock:

Balance at beginning of period $ 405 $ 401

Issuance of common stock — —

Balance at September 30 $ 405 $ 401

Additional paid-in capital:

Balance at beginning of period $ 724,159 $ 713,542

Issuance of common stock 3,402 2,553

Balance at September 30 $ 727,561 $ 716,095

Stock notes receivable:

Balance at beginning of period $ — $ ( 5,233 )

Employee equity transactions — 5,233

Balance at September 30 $ — $ —

Accumulated other comprehensive income (loss):

Balance at beginning of period $ ( 2,666 ) $ ( 31,136 )

Other comprehensive income, net of tax 12,205 29,433

Balance at September 30 $ 9,539 $ ( 1,703 )

Retained earnings:

Balance at beginning of period $ 178,017 $ 46,046

Net income 45,901 36,668

Balance at September 30 $ 223,918 $ 82,714

Total stockholders’ equity $ 961,423 $ 797,507

The accompanying notes are an integral part of the consolidated financial statements.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

CONDENSED CONSOLIDATED STATEMENTS OF STOCKHOLDERS’ EQUITY (UNAUDITED)

Nine months ended September 30,

Three months ended March 31,

($ in thousands, except share amounts) 2026 2025

2 unchanged sentences

Issuance of shares 4,031,843 274,971

Balance at September 30 40,487,365 40,099,931

Balance at March 31, 44,543,065 40,402,879

Treasury shares:

Balance at beginning of year — —

Shares acquired 185,022 —

Balance at March 31, 185,022 —

Common stock:

1 unchanged sentence

Issuance of common stock 79 3

Balance at September 30 $ 405 $ 401

Balance at March 31, $ 484 $ 404

Treasury stock:

Balance at beginning of year $ — $ —

Treasury stock acquired ( 8,665 ) —

Balance at March 31, $ ( 8,665 ) $ —

Additional paid-in capital:

1 unchanged sentence

Issuance of common stock 191,756 2,588

Balance at September 30 $ 727,561 $ 716,095

Stock notes receivable:

Balance at beginning of year $ — $ ( 5,562 )

Employee equity transactions — 5,562

Balance at September 30 $ — $ —

Accumulated other comprehensive income (loss):

Balance at March 31, $ 922,311 $ 721,186

Accumulated other comprehensive loss:

Balance at beginning of year $ 11,457 $ ( 22,120 )

Other comprehensive income, net of tax 31,659 21,250

Balance at September 30 $ 9,539 $ ( 1,703 )

Retained earnings (accumulated deficit):

Other comprehensive (loss) income, net of tax ( 17,583 ) 12,073

Balance at March 31, $ ( 6,126 ) $ ( 10,047 )

Retained earnings:

Balance at beginning of year $ 267,148 $ 97,120

Net income 49,731 42,058

Balance at September 30 $ 223,918 $ 82,714

Balance at March 31, $ 316,879 $ 139,178

Total stockholders’ equity $ 1,224,883 $ 850,721

3 unchanged sentences

CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS (UNAUDITED)

Nine months ended September 30,

Three months ended March 31,

($ in thousands) 2026 2025

4 unchanged sentences

Cash flows from investing activities:

Net cash paid in acquisition ( 303,035 ) —

Purchase of fixed maturity securities, available-for-sale ( 269,921 ) ( 126,827 )

1 unchanged sentence

Purchase of equity method investments and other long-term investments ( 283 ) ( 200 )

Purchase of intangible assets and goodwill ( 2,000 ) —

Investment in direct and indirect loans 442 13,829

Purchase of property and equipment ( 3,747 ) ( 3,148 )

Proceeds from the sales of (payments for the purchase of) property and equipment 1,654 ( 202 )

Proceeds from the sales of fixed maturity securities, available-for-sale 84,032 8,195

8 unchanged sentences

Cash flows from financing activities:

Repayment of stock notes receivable — 5,561

Proceeds from issuance of common stock 200 —

Proceeds from long term borrowings 371,089 —

Payments on long term borrowings and trust preferred — ( 116,794 )

Net cash used in financing activities — ( 4,233 )

Treasury stock acquired ( 8,665 ) —

Net cash provided by financing activities 362,624 —

Net increase in cash and cash equivalents and restricted cash 117,317 ( 4,019 )

5 unchanged sentences

Cash paid for interest $ 6,246 $ 1,805

Cash paid for income taxes $ 31,822 $ 22,968

(1) The sum of cash and cash equivalents and restricted cash from the consolidated balance sheets

2 unchanged sentences

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Summary of Significant Accounting Policies

12 unchanged sentences

Updates to Significant Accounting Policies

The following accounting policy has been updated to align with reporting of peer companies.

Available-for-sale

The allowance for credit losses is limited to the amount by which fair value is below amortized cost.

Prior to September 30, 2025, changes in the allowance for credit losses were recognized in net investment income on the consolidated statements of operations.

As of September 30, 2025, changes in the allowance for credit losses are recognized in net investment gains.

Prior periods have been updated to conform to the current period presentation.

Credit losses that are limited by the fair value of the security are recognized in stockholders’ equity, net of taxes, as a component of accumulated other comprehensive (loss) income.

Unrealized losses that are not credit-related continue to be recognized in stockholders’ equity, net of taxes, as a component of accumulated other comprehensive (loss) income.

Held to maturity

Investments in fixed maturity securities that are held-to-maturity are carried at amortized cost net of an allowance for credit losses.

The allowance for credit losses represents the current estimate of expected credit losses.

The Company develops a historical loss rate from Moody’s multi-year cumulative loss rates for asset backed securities.

The historical loss rate is adjusted for current conditions and reasonable and supportable forecasts.

Prior to September 30, 2025, changes in the allowance for credit losses were recognized in net investment income on the consolidated statements of operations.

As of September 30, 2025, changes in the allowance for credit losses are recognized in net investment gains.

Prior periods have been updated to conform to the current period presentation.

Consolidation

Variable interest entity

The Company consolidates an entity in which it has a controlling financial interest by first considering if an entity meets the definition of a variable interest entity ("VIE") for which the Company is deemed to be the primary beneficiary, or if the Company has the power to control an entity through a majority of voting interest or through other arrangements.

A VIE is an entity that either (i) lacks sufficient equity to finance its activities without additional subordinated financial support from other parties;

(ii) whose equity holders lack the characteristics of a controlling financial interest;

and/or (iii) is established with non-substantive voting rights.

The Company’s assessment may involve subjectivity in the determination of

The following accounting policies have been updated following the Apollo Group Holdings Limited (“Apollo”) acquisition on January 1, 2026.

Description of Business

Skyward Specialty Insurance Group, Inc.

(the “Company”), an insurance holding company, is a Delaware corporation that was organized in 2006.

It is a specialty insurance company operating in two segments delivering commercial property and casualty products insurance coverages.

The Company has four wholly owned insurance company subsidiaries based in the United States:

• Great Midwest Insurance Company (“GMIC”) underwrites insurance on an admitted basis and is a certified surety bond company listed with the U.S.

Department of the Treasury.

• Houston Specialty Insurance Company (“HSIC”), a subsidiary of GMIC, underwrites insurance on a non-admitted basis.

• Imperium Insurance Company (“IIC”), a subsidiary of HSIC, underwrites insurance on an admitted basis.

• Oklahoma Specialty Insurance Company (“OSIC”), a subsidiary of IIC, underwrites insurance on a non-admitted basis.

The Company has a wholly owned captive reinsurance company subsidiary, Skyward Re, that is domiciled in the Cayman Islands and assumed net reserves for certain divisions, related to a retroactive reinsurance contract, from the Company’s insurance companies and retroceded the net reserves to a third-party reinsurer.

The Company has three non-risk bearing wholly owned subsidiaries, (i) Skyward Underwriters Agency, Inc.

(“SUA”),a managing general insurance agent and reinsurance broker for property and casualty risks in specialty niche markets, (ii) Skyward Service Company an entity which provides various administrative services to the Company’s subsidiaries, and (iii) Skyward Specialty No.

1 Limited, a Lloyd’s corporate member authorized to invest in Lloyd’s syndicates.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO UNAUDITED CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

which activities most significantly affect the VIE’s performance, and estimates about current and future fair value of the assets held by the VIE and financial performance of the VIE.

In performing the related party analysis, the Company considers both qualitative and quantitative factors, including, but not limited to:

the characteristics and size of its investment relative to the related party;

the Company’s and the related party's ability to control or significantly influence key decisions of the VIE including consideration of involvement by de facto agents;

the obligation or likelihood for the Company or the related party to fund operating losses of the VIE;

and the similarity and significance of the VIE’s business activities to those of the Company and the related party.

The determination of whether an entity is a VIE, and whether the Company is the primary beneficiary, may involve significant judgment, and depends upon facts and circumstances specific to an entity at the time of the assessment.

At each reporting period, the Company reassesses whether changes in facts and circumstances cause a change in the status of an entity as a VIE, and/or a change in the Company's consolidation assessment.

Changes in consolidation status are applied prospectively.

An entity may be consolidated as a result of this reassessment, in which case, the assets, liabilities and noncontrolling interest in the entity are recorded at fair value upon initial consolidation.

Any existing equity interest held by the Company in the entity prior to the Company obtaining control will be remeasured at fair value, which may result in a gain or loss recognized upon initial consolidation.

The Company may also deconsolidate a subsidiary as a result of this reassessment, which may result in a gain or loss recognized upon deconsolidation depending on the carrying values of deconsolidated assets and liabilities compared to the fair value of any interests retained.

After performing the above assessments, the Company has determined one entity meets the definition of a VIE for which the Company is the primary beneficiary.

See Note 6 for further details and required disclosures.

The Company uses commodity derivatives to assume risk and manage its exposures in the insurance industry.

Commodity derivatives expose the Company to potentially unfavorable price changes to the underlying commodities.

The Company accounts for its derivatives in accordance with FASB ASC Topic 815, Derivatives and Hedging, which requires all derivatives to be recorded at fair value on the Company’s balance sheet as either assets or liabilities, depending on their rights or obligations, with changes in fair value reflected in current earnings.

The Company meets the criteria in the guidance to net the assets and liabilities, which the Company includes in “other assets” on the condensed consolidated balance sheets.

While the Company considers these exchange-traded futures and forward purchase and sale contracts to be effective economic hedges, the Company has not elected hedge accounting treatment.

The fair value of the Company’s derivatives is estimated by reference to quoted prices or broker quotes, where available, or in the absence of quoted prices or broker quotes, the use of industry or internal valuation models.

See Note 7 for further details and required disclosures.

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Summary of Significant Accounting Policies (continued)

On January 1, 2026, the Company completed its acquisition of Apollo Group Holdings Limited (“Apollo”), a Lloyd’s of London (“Lloyd’s”) specialist insurance and reinsurance group.

Apollo includes a Lloyd’s of London Managing Agency, Apollo Syndicate Management Limited (“ASML”), which provides managing agency services to nine Lloyd’s syndicates.

Syndicate 1969, underwrites a diversified specialty portfolio, Syndicate 1971 focuses on digital‑economy and technology‑enabled risks, and Syndicate 1972 provides reinsurance for Apollo managed syndicates and provides a quota share facility for Syndicates 1969 and 1971.

Apollo participates in its wholly managed syndicates through its corporate member company, Apollo No.

16 Limited (“Apollo No.

16”) which has a quota share agreement in place with Apollo Bermuda Limited.

Commission and Fee Income and Underwriting Fee Income

Managing Agency Fees and Profit Commission

ASML earns a fee for providing managing agency services (such as underwriting oversight, operational administration and regulatory compliance) to the syndicates it manages.

These managing agency fees are based on each syndicate’s annual capacity and are recognized over the period of services provided.

ASML may also earn profit commission under contractual arrangements with the capital providers to each syndicate.

Profit commission is contingent on syndicate profitability and is accrued in accordance with the contractual terms and the subsequent development of underwriting results at the balance sheet date.

Amounts are generally not payable until the underlying underwriting results have substantially matured (typically around 36 months after inception), unless interim profit distributions permit earlier payments on account.

Intra‑group managing agency fees and profit commission are eliminated on consolidation.

Other Revenue From Management Services

Apollo also earns other services revenue for other administrative and operational services performed for the syndicates it manages, including those supported primarily by third‑party capital providers.

Such revenue is measured at the fair value of consideration received or receivable and includes service fees and consortium income.

Consortium income represents fees charged to consortia members for whom ASML acts as consortium leader and is recognized at the point in time premiums are written;

amounts related to underwriting services provided over multi‑year periods are deferred accordingly.

Foreign Currency

The Company transacts business in numerous currencies through business units located around the world.

The functional currency for each business unit is determined by the local currency used for most economic activity in that area.

Movements in exchange rates related to transactions in currencies other than a business unit’s functional currency for monetary assets and liabilities are remeasured through the consolidated statements of operations and comprehensive income (loss) in other income (expense), except for currency movements related to available for sale fixed maturities securities, which are excluded from net income (loss) and accumulated in stockholder’s equity, net of deferred taxes.

The business units’ functional currency financial statements are translated to the Company’s reporting currency, U.S.

dollars, using the exchange rates at the end of period for the balance sheets and the average exchange rates in effect for the reporting period for the statements of operations and comprehensive income.

Gains and losses resulting from translating the foreign currency financial statements, net of deferred income taxes, are excluded from net income and accumulated as a separate component of accumulated other comprehensive income in stockholder’s equity.

Reclassifications

During the current period, the Company reclassified amounts previously included in “Other assets” to separate line items on the balance sheet for “Funds at Lloyd’s” and “Options, at fair value” to better reflect the nature of these balances.

Prior period amounts have been reclassified to conform to the current presentation.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

The following tables set forth the amortized cost and the fair value by investment category at September 30, 2025 and December 31, 2024:

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Goodwill and Intangible Assets

The following tables set forth the carrying amount and changes in the balance of goodwill by reporting unit at March 31, 2026 and 2025:

($ in thousands) Accident

and Health Credit & Surety Energy Solutions Apollo Other Total

Gross balance at December 31, 2025 $ 91,577 $ 6,781 $ 10,204 $ — $ 3,879 $ 112,441

Accumulated impairment at December 31, 2025 ( 44,821 ) — — — ( 1,886 ) ( 46,707 )

Additions — — — 125,408 — 125,408

Net balance at March 31, 2026 $ 46,756 $ 6,781 $ 10,204 $ 125,408 $ 1,993 $ 191,142

($ in thousands) Accident

and Health Credit & Surety Energy Solutions Other Total

Gross balance at December 31, 2024 $ 91,577 $ 6,781 $ 10,204 $ 3,879 $ 112,441

Accumulated impairment at December 31, 2024 ( 44,821 ) — — ( 1,886 ) ( 46,707 )

Net balance at March 31, 2025 $ 46,756 $ 6,781 $ 10,204 $ 1,993 $ 65,734

The following tables set forth the carrying amount and changes in the balance of other intangible assets at March 31, 2026 and 2025:

($ in thousands) Agent

Relationships Non-competes Trademarks Syndicate Capacity Licenses Total

Other Intangible Assets

Gross balance at December 31, 2025 $ 26,491 $ 1,117 $ 999 $ — $ 14,019 $ 42,626

Accumulated amortization at December 31, 2025 ( 19,203 ) ( 1,117 ) — — — ( 20,320 )

Additions 27,000 — 35,000 200,000 — 262,000

Amortization ( 1,257 ) — ( 875 ) — — ( 2,132 )

Net balance at March 31, 2026 $ 33,031 $ — $ 35,124 $ 200,000 $ 14,019 $ 282,174

($ in thousands) Agent

Relationships Non-competes Trademarks Licenses Total

Other Intangible Assets

Gross balance at December 31, 2024 $ 24,491 $ 1,117 $ 999 $ 14,019 $ 40,626

Accumulated amortization at December 31, 2024 ( 17,895 ) ( 1,117 ) — — ( 19,012 )

Amortization ( 259 ) — — — ( 259 )

Net balance at March 31, 2025 $ 6,337 $ — $ 999 $ 14,019 $ 21,355

The Company’s indefinite lived intangible assets relate to insurance licenses, trademarks and Lloyd’s syndicates capacity.

Its finite lived intangible assets, which relate to policy renewals, agency relationships, within agent relationships, finite syndicates capacity relationships and non-compete/exclusivity agreements, within non-competes, have a weighted average useful life of approximately 9 years as of March 31, 2026.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Goodwill and Intangible Assets (continued)

The Company recognized approximately $ 2.1 million and $ 0.3 million in amortization expense for the three months ended March 31, 2026 and 2025, respectively.

The following table sets forth the estimated future net amortization expense of intangible assets:

($ in thousands)

Remainder of 2026 $ 6,394

Year Ending December 31, 2027 8,525

Year Ending December 31, 2028 8,525

Year Ending December 31, 2029 8,233

Year Ending December 31, 2030 8,025

The following tables set forth the amortized cost and the fair value by investment category at March 31, 2026 and December 31, 2025:

($ in thousands) Amortized

Losses Allowance for Credit Losses Fair Value

September 30, 2025

March 31, 2026

Fixed maturity securities, available-for-sale:

government securities $ 160,144 $ 178 $ ( 774 ) $ — $ 159,548

Non U.S government securities 2,696 — ( 25 ) — 2,671

Corporate securities and miscellaneous 807,859 8,007 ( 8,881 ) ( 6,500 ) 800,485

7 unchanged sentences

Total fixed maturity securities, held-to-maturity $ 30,395 $ 4,196 $ — $ ( 301 ) $ 34,290

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Investments (continued)

($ in thousands) Amortized

12 unchanged sentences

Total fixed maturity securities, held-to-maturity $ 33,290 $ 829 $ ( 48 ) $ ( 468 ) $ 33,603

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Investments (continued)

The following table sets forth the amortized cost and fair value of available-for-sale fixed maturity securities by contractual maturity at September 30, 2025:

The following table sets forth the amortized cost and fair value of available-for-sale fixed maturity securities by contractual maturity at March 31, 2026:

($ in thousands) Amortized

9 unchanged sentences

Also, changing interest rates, tax considerations or other factors may result in portfolio sales prior to maturity.

The Company’s fixed maturity securities, held-to-maturity, at September 30, 2025 consisted entirely of asset backed securities that were not due at a single maturity date.

At September 30, 2025, the Company had U.S.

The Company’s fixed maturity securities, held-to-maturity, at March 31, 2026 consisted entirely of asset backed securities that were not due at a single maturity date.

At March 31, 2026, the Company had U.S.

government agencies mortgage-backed fixed maturity securities, with a carrying value of approximately $ 71.3 million pledged as collateral for a loan (the “FHLB Loan”) from the Federal Home Loan Bank of Dallas (“FHLB”) pursuant to an Advances and Security Agreement between the Company and FHLB (the “Advances and Security Agreement”).

In accordance with the terms of the FHLB Loan, the Company retains all rights regarding these pledged securities.

At September 30, 2025, the Company had assets with fair values of approximately $ 55.3 million pledged as collateral for performance obligations under reinsurance agreements.

At March 31, 2026, the Company had assets with fair values of approximately $ 77.5 million pledged as collateral for performance obligations under reinsurance agreements.

In accordance with the terms of the trust agreements, the Company retains all rights regarding these securities, of which $ 63.2 million are residential mortgage-backed securities, $ 12.1 million of cash and cash equivalents and other assets and $ 2.2 million of short-term investments.

The following tables set forth the gross unrealized losses and the corresponding fair values of investments, aggregated by length of time that individual securities had been in a continuous unrealized loss position as of September 30, 2025 and 2024:

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Investments (continued)

Less than 12 Months 12 Months or More Total

($ in thousands) Fair Value Gross Unrealized Losses Fair Value Gross Unrealized Losses Fair Value Gross Unrealized Losses

September 30, 2025

March 31, 2026

Fixed maturity securities, available-for-sale:

government securities $ 91,541 $ ( 769 ) $ 707 $ ( 5 ) $ 92,248 $ ( 774 )

government securities 2,671 ( 25 ) — — 2,671 ( 25 )

Corporate securities and miscellaneous 341,776 ( 4,883 ) 57,293 ( 3,998 ) 399,069 ( 8,881 )

3 unchanged sentences

Other asset-backed securities 328,244 ( 2,584 ) 7,783 ( 907 ) 336,027 ( 3,491 )

Total fixed maturity securities, available-for-sale 182,806 ( 1,104 ) 203,531 ( 17,403 ) 386,337 ( 18,507 )

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Investments (continued)

Total $ 929,701 $ ( 9,595 ) $ 163,373 $ ( 16,513 ) $ 1,093,074 $ ( 26,108 )

Less than 12 Months 12 Months or More Total

14 unchanged sentences

Total $ 234,953 $ ( 1,484 ) $ 185,663 $ ( 15,394 ) $ 420,616 $ ( 16,878 )

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Investments (continued)

The Company regularly monitors its available-for-sale fixed maturity securities that have fair values less than cost or amortized cost for signs of impairment, an assessment that requires significant management judgment regarding the evidence known.

1 unchanged sentence

Among the factors that management considers for fixed maturity securities are the financial condition of the issuer including receipt of scheduled principal and interest cash flows, and intent to sell, including if it is more likely than not that the Company will be required to sell the investments before recovery.

As of September 30, 2025, the Company had 515 lots of fixed maturity securities in an unrealized loss position.

As of March 31, 2026, the Company had 1,057 lots of fixed maturity securities in an unrealized loss position.

The Company does not have an intent to sell these securities and it is not more likely than not that the Company will be required to sell these securities before maturity or recovery of its cost basis.

The Company reviewed its investments at September 30, 2025 and determined that for two available-for-sale securities in the “corporate securities and miscellaneous” category, credit impairments existed, based on new recovery analysis that showed deteriorating conditions raising credit concerns.

The Company reviewed its investments at March 31, 2026 and determined that for two available-for-sale securities in the “corporate securities and miscellaneous” category, credit impairments existed, based on new recovery analysis that showed deteriorating conditions raising credit concerns.

Other than the securities discussed previously, the Company determined that no other credit impairment existed in the gross unrealized holding losses, due to the reasons discussed below:

5 unchanged sentences

Therefore, the Company does not consider these impaired securities.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Investments (continued)

• Corporate securities and miscellaneous :

9 unchanged sentences

Therefore, the Company does not consider these impaired securities.

The following table sets forth the changes in the allowance for credit losses on available-for-sale securities and held-to-maturity securities during the nine months ended September 30, 2025 and 2024:

The following table sets forth the changes in the allowance for credit losses on available-for-sale securities and held-to-maturity securities during the three months ended March 31, 2026 and 2025:

($ in thousands) Fixed Maturity Securities, Available-For-Sale Fixed Maturity Securities, Held-to-Maturity

Balance at December 31, 2025 $ 7,000 $ 468

Current period provision for credit losses — 7

Balance at March 31, 2025 $ — $ 250

Current period provision for credit losses 6,150 18

Balance at June 30, 2025 $ 6,150 $ 268

Current period provision for credit losses 850 —

Recoveries of amounts previously written off ( 500 ) ( 167 )

Balance at September 30, 2025 $ 7,000 $ 236

Balance at March 31, 2026 $ 6,500 $ 301

Fixed Maturity Securities, Held-to-Maturity

Balance at December 31, 2024 $ 243

Balance at March 31, 2024 $ 329

Recoveries of amounts previously written off ( 104 )

Balance at June 30, 2024 $ 225

Current period provision for credit losses 7

Balance at September 30, 2024 $ 239

Balance at March 31, 2025 $ 250

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Investments (continued)

The following table sets forth the components of net investment gains for the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30, Nine months ended September 30,

The following table sets forth the components of net investment gains for the three months ended March 31, 2026 and 2025:

($ in thousands) 2026 2025

2 unchanged sentences

Equity securities — 1,745

Other 109 62 709 170

Total 1,807 2,202

10 unchanged sentences

$ 3,185 $ 6,750

The following table sets forth the proceeds from sales of available-for-sale fixed maturity securities and equity securities for the nine months ended September 30, 2025 and 2024:

Nine months ended September 30,

The following table sets forth the proceeds from sales of available-for-sale fixed maturity securities and equity securities for the three months ended March 31, 2026 and 2025:

($ in thousands) 2026 2025

1 unchanged sentence

Equity securities — 8,748

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Investments (continued)

The following table sets forth the components of net investment income for the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30, Nine months ended September 30,

The following table sets forth the components of net investment income for the three months ended March 31, 2026 and 2025:

($ in thousands) 2026 2025

11 unchanged sentences

Net investment income $ 27,055 $ 19,422

The following table sets forth the change in net unrealized gains (losses) on the Company’s investment portfolio, net of deferred income taxes, included in other comprehensive loss for the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30, Nine months ended September 30,

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Investments (continued)

($ in thousands) 2026 2025

2 unchanged sentences

Total $ ( 17,583 ) $ 12,073

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Fair Value Measurements

28 unchanged sentences

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Fair Value Measurements (continued)

The following table sets forth the range of the discount rate as of September 30, 2025 and December 31, 2024:

September 30, 2025 December 31, 2024

The following table sets forth the range of the discount rate as of March 31, 2026 and December 31, 2025:

March 31, 2026 December 31, 2025

High 11.35 % 11.10 %

6 unchanged sentences

The spread represents the incremental cost of capital based on the borrower’s ability to make future payments and the value of the collateral relative to the loan balance and is subject to judgment and uncertainty.

The following table sets forth the range and weighted average, weighted by relative fair value, of the spread as of September 30, 2025 and December 31, 2024:

September 30, 2025 December 31, 2024

The following table sets forth the range and weighted average, weighted by relative fair value, of the spread as of March 31, 2026 and December 31, 2025:

March 31, 2026 December 31, 2025

High 8.09 % 8.34 %

6 unchanged sentences

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Fair Value Measurements (continued)

The following tables set forth the Company’s investments and derivatives within the fair value hierarchy at September 30, 2025 and December 31, 2024:

September 30, 2025

The following tables set forth the Company’s investments and derivatives within the fair value hierarchy at March 31, 2026 and December 31, 2025:

March 31, 2026

($ in thousands) Level 1 Level 2 Level 3 Total

1 unchanged sentence

government securities $ 159,548 $ — $ — $ 159,548

Non U.S government securities — 2,671 — 2,671

Corporate securities and miscellaneous — 658,638 141,847 800,485

8 unchanged sentences

Equity securities:

Common stocks — — — —

Preferred stocks — 1,140 — 1,140

Mutual funds — — — —

Total equity securities — 1,140 — 1,140

5 unchanged sentences

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Fair Value Measurements (continued)

14 unchanged sentences

Equity securities:

Common stocks 64,251 — — 64,251

Preferred stocks — 1,174 — 1,174

Mutual funds 40,839 — — 40,839

Total equity securities — 1,174 — 1,174

1 unchanged sentence

Short-term investments 264,299 — — 264,299

Derivatives 34,857 — — 34,857

Total $ 343,624 $ 1,662,092 $ 194,422 $ 2,200,138

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Fair Value Measurements (continued)

The following tables set forth the changes in the fair value of instruments carried at fair value with a Level 3 measurement during the nine months ended September 30, 2025 and 2024:

The following tables set forth the changes in the fair value of instruments carried at fair value with a Level 3 measurement during the three months ended March 31, 2026 and 2025:

($ in thousands) Fixed Maturity Securities, Available-For-Sale Mortgage Loans

1 unchanged sentence

Total losses for the period recognized in net investment gains ( 62 ) ( 814 )

Issuances — 5

Settlements — ( 10,417 )

Purchases 11,266 —

Sales/Disposals ( 334 ) —

Total unrealized gains for the period recognized in accumulated comprehensive income (loss) 682 —

Total unrealized losses for the period recognized in accumulated comprehensive (loss) income ( 2,337 ) —

Balance at March 31, 2026 $ 159,450 $ 9,088

Total losses for the period recognized in net investment gains attributable to the change in unrealized gains or losses relating to assets held as of period end $ — $ ( 84 )

Total (losses) gains for the period recognized in net investment gains ( 4,081 ) 330

Issuances — 8

Settlements — ( 6,182 )

Transfers into Level 3 6,144 —

Purchases 8,838 —

Sales/Disposals ( 237 ) —

Total unrealized gains for the period recognized in accumulated comprehensive income (loss) 747 —

Balance at June 30, 2025 $ 94,868 $ 10,168

Total gains for the period recognized in net investment gains attributable to the change in unrealized gains or losses relating to assets held as of period end $ — $ 92

($ in thousands) Fixed Maturity Securities, Available-For-Sale Mortgage Loans

Balance at December 31, 2024 $ 77,920 $ 26,490

Total losses for the period recognized in net investment gains ( 110 ) ( 66 )

Issuances — 5

Settlements — ( 10,417 )

2 unchanged sentences

Total unrealized gains for the period recognized in accumulated comprehensive income (loss) 682 —

Balance at September 30, 2025 $ 119,227 $ 9,998

Balance at March 31, 2025 $ 83,457 $ 16,012

Total losses for the period recognized in net investment gains attributable to the change in unrealized gains or losses relating to assets held as of period end $ — $ ( 84 )

1 unchanged sentence

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Fair Value Measurements (continued)

($ in thousands) Fixed Maturity Securities, Available-For-Sale Equity Securities Mortgage Loans

Balance at December 31, 2023 $ — $ — $ 50,070

Total gains for the period recognized in net investment gains (losses) — — 971

Issuances — — 187

Settlements — — ( 6,919 )

Balance at March 31, 2024 $ — $ — $ 44,309

Total gains for the period recognized in net investment gains (losses) attributable to the change in unrealized gains or losses relating to assets held as of period end $ — $ — $ 952

Total losses for the period recognized in net investment gains (losses) — — ( 1,030 )

Issuances — — 449

Settlements — — ( 58 )

Balance at June 30, 2024 $ — $ — $ 43,670

Total losses for the period recognized in net investment gains (losses) attributable to the change in unrealized gains or losses relating to assets held as of period end $ — $ — $ ( 1,031 )

Total (losses) gains for the period recognized in net investment gains (losses) ( 118 ) 246 866

Total unrealized gains for the period recognized in accumulated comprehensive income (loss) 1,592 — —

Transfers into Level 3 23,533 — —

Purchases 23,820 5,571 —

Sales/Disposals ( 153 ) — —

Issuances — — 8

Settlements — — ( 8,277 )

Balance at September 30, 2024 $ 48,674 $ 5,817 $ 36,267

Total gains for the period recognized in net investment gains (losses) attributable to the change in unrealized gains or losses relating to assets held as of period end $ — $ 246 $ 829

The transfers into Level 3 during the nine months ended September 30, 2025 were the result of securities that began receiving valuations from asset managers that utilized unobservable inputs at the end of the period.

The transfers into Level 3 during the three months ended March 31, 2026 were the result of securities that began receiving valuations from asset managers that utilized unobservable inputs at the end of the period.

The Company measures certain assets, including investments in indirect loans and loan collateral, equity method investments and other invested assets, at fair value on a nonrecurring basis only when they are deemed to be impaired.

7 unchanged sentences

Fixed maturity securities, held-to-maturity consists of senior and junior notes with target rates of return.

As of September 30, 2025, the Company determined the fair value of these instruments using the income approach utilizing inputs that are unobservable (Level 3).

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO(UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Fair Value Measurements (continued)

As of March 31, 2026, the Company determined the fair value of these instruments using the income approach utilizing inputs that are unobservable (Level 3).

Investment in RedBird Capital Partners:

Included in other long-term investments is an investment in a limited partnership with RedBird Capital Partners, which invests in Bishop Street Underwriters, LLC (“Bishop Street”), a managing general agent (MGA).

The investment had a fair value of $ 47.0 million at September 30, 2025, which was determined using the net asset value.

The investment had a fair value of $ 47.2 million at March 31, 2026, which was determined using the net asset value.

The Company employs procedures to assess the reasonableness of the fair value of the investment including obtaining and reviewing the audited financial statements.

The unfunded commitment related to the investment was $ 21.5 million at September 30, 2025.

The unfunded commitment related to the investment was $ 18.3 million at March 31, 2026.

The Company may sell its interest in the investment with the appropriate prior written notice and approval by the general partner.

6 unchanged sentences

The Company determines the fair value of these instruments using the income approach utilizing inputs that are observable (Level 2).

The following table sets forth the Company’s carrying and fair values of notes payable and subordinated debt as of September 30, 2025 and December 31, 2024:

September 30, 2025 December 31, 2024

The following table sets forth the Company’s carrying and fair values of notes payable and subordinated debt as of March 31, 2026 and December 31, 2025:

March 31, 2026 December 31, 2025

($ in thousands) Carrying

3 unchanged sentences

Revolving Credit Facility 114,500 114,500 114,500 114,500

Term Loan Facility, net of debt issuance costs 294,918 294,207 300,000 300,000

Notes payable $ 466,418 $ 465,819 $ 471,500 $ 471,958

3 unchanged sentences

Other financial instruments qualify as insurance-related products and are specifically exempted from fair value disclosure requirements.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Mortgage Loans

The Company has invested in Separately Managed Accounts (“SMA1” and “SMA2”).

As of September 30, 2025 and December 31, 2024, the Company held direct investments in mortgage loans from various creditors through SMA1 and SMA2.

As of March 31, 2026 and December 31, 2025, the Company held direct investments in mortgage loans from various creditors through SMA1 and SMA2.

The Company’s mortgage loan portfolios are primarily senior loans on real estate across the U.S.

1 unchanged sentence

The principal amounts of the loans are approximately 64 % of the property’s appraised value at the time the loans were made.

The following table sets forth the carrying value of the Company’s mortgage loans as of September 30, 2025 and December 31, 2024:

($ in thousands) September 30, 2025 December 31, 2024

The following table sets forth the carrying value of the Company’s mortgage loans as of March 31, 2026 and 2025:

($ in thousands) March 31, 2026 December 31, 2025

Commercial $ 2,468 $ 3,334

Retail — 10,032

Hospitality 6,620 6,568

$ 9,088 $ 9,902

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Mortgage Loans (continued)

The following table sets forth the Company’s gross investment income for mortgage loans for the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30, Nine months ended September 30,

The following table sets forth the Company’s gross investment income for mortgage loans for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

($ in thousands) 2026 2025

Commercial $ ( 824 ) $ 108

Retail — 513 304 1,473

Hospitality 159 249

2 unchanged sentences

The Company writes off the uncollectible amount in the period it was determined to be uncollectible.

There was no write-off for uncollectible amounts during the three and nine months ended September 30, 2025 and 2024, respectively.

As of September 30, 2025 and as of December 31, 2024, no mortgage loans were in the process of foreclosure and there were no mortgage loans that were not producing income for the previous 12 months.

There was no write-off for uncollectible amounts during the three months ended March 31, 2026 and 2025, respectively.

As of March 31, 2026 and as of December 31, 2025, $ 2.5 million mortgage loans were in the process of foreclosure and there was 1 mortgage loan that was not producing income for the previous 12 months.

Equity Method Investments and Other

The following table sets forth the carrying value and ownership percentage of the Company’s equity method investments as of September 30, 2025 and December 31, 2024:

($ in thousands) September 30, 2025 December 31, 2024

The following table sets forth the carrying value and ownership percentage of the Company’s equity method investments as of March 31, 2026 and 2025:

($ in thousands) March 31, 2026 December 31, 2025

Carrying Value Ownership % Carrying Value Ownership %

9 unchanged sentences

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Equity Method Investments and Other (continued)

The following table sets forth the components of net investment income (loss) from equity method investments for the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30, Nine months ended September 30,

The following table sets forth the components of net investment income (loss) from equity method investments for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

($ in thousands) 2026 2025

7 unchanged sentences

$ ( 1,297 ) $ ( 1,988 )

The following table sets forth the unfunded commitment of equity method investments as of September 30, 2025 and December 31, 2024:

($ in thousands) September 30, 2025 December 31, 2024

The following table sets forth the unfunded commitment of equity method investments as of March 31, 2026 and December 31, 2025:

($ in thousands) March 31, 2026 December 31, 2025

Brewer Lane Ventures Fund II LP units $ 2,650 $ 3,237

1 unchanged sentence

Hudson Ventures Fund 2 LP units 166 166

Red Bird Capital Partners LP units 21,506 24,400

$ 3,202 $ 3,789

3 unchanged sentences

The Company amortizes this difference over a 15 -year useful life.

The following table sets forth the Company’s recorded investment in RISCOM compared to its share of underlying equity as of September 30, 2025 and December 31, 2024:

($ in thousands) September 30, 2025 December 31, 2024

The following table sets forth the Company’s recorded investment in RISCOM compared to its share of underlying equity as of March 31, 2026 and December 31, 2025:

($ in thousands) March 31, 2026 December 31, 2025

Investment in RISCOM:

2 unchanged sentences

Recorded investment balance $ 4,026 $ 3,307

The following table sets forth the Company’s recorded investment in JVM Funds LLC compared to its share of underlying equity as of September 30, 2025 and December 31, 2024:

($ in thousands) September 30, 2025 December 31, 2024

The following table sets forth the Company’s recorded investment in JVM Funds LLC compared to its share of underlying equity as of March 31, 2026 and December 31, 2025:

($ in thousands) March 31, 2026 December 31, 2025

Investment in JVM Funds LLC:

2 unchanged sentences

Recorded investment balance $ 14,155 $ 14,911

Investment in Indirect Loans and Loan Collateral

As of March 31, 2026 and December 31, 2025, the Company held indirect investments in collateralized loans and loan collateral through SMA1 and SMA2.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Equity Method Investments and Other (continued)

Investment in Indirect Loans and Loan Collateral

As of September 30, 2025 and December 31, 2024, the Company held indirect investments in collateralized loans and loan collateral through SMA1 and SMA2.

The carrying value of the SMA1 and SMA2 as of September 30, 2025 and December 31, 2024 were as follows:

($ in thousands) September 30, 2025 December 31, 2024

The carrying value of the SMA1 and SMA2 as of March 31, 2026 and December 31, 2025 were as follows:

($ in thousands) March 31, 2026 December 31, 2025

SMA1 $ 13,823 $ 15,418

11 unchanged sentences

In addition, there is no recourse to the assets of HSIC-01 other than to satisfy associated liabilities.

The following table presents the assets of HSIC-01, included in the condensed consolidated balance sheet as of September 30, 2025.

The following table presents the assets of HSIC-01, included in the condensed consolidated balance sheet as of March 31, 2026.

The assets presented below only include third-party net assets and exclude any intercompany balances, which were eliminated upon consolidation.

($ in thousands) September 30, 2025

($ in thousands) March 31, 2026

Cash and cash equivalents 20,196

Other assets 16,843

Options, at fair value 24,401

Total assets $ 44,597

7 unchanged sentences

The Company has not elected hedge accounting for these derivatives.

The following table presents the notional amounts and fair value of derivative assets in the condensed consolidated balance sheets at September 30, 2025:

The following table presents the notional amounts and fair value of derivative assets in the condensed consolidated balance sheets at March 31, 2026:

($ in thousands) Derivative Assets

1 unchanged sentence

Economic hedges $ 188,191 $ 24,401

The Company presents the net gain (loss) recognized on derivative instruments in economic hedging relationships in “losses and loss adjustment expenses” on the condensed consolidated statements of operations.

For the three months ended March 31, 2026, the Company recognized $ 31.3 million, respectively, of pre-tax net losses in losses and loss adjustment expenses.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Derivatives (continued)

For the three and nine months ended September 30, 2025, the Company recognized $ 5.2 million, respectively, of pre-tax net gains in losses and loss adjustment expenses .

The Company has one reportable segment through which it offers a broad array of commercial property and casualty products and solutions on a non-admitted (or E&S) and admitted basis, predominantly in the United States.

The segment is made up of nine distinct underwriting divisions, or “continuing business,” and has dedicated underwriting leadership supported by high-quality technical staff with deep experience in their respective niches.

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Notes Payable & Subordinated Debt

On August 30, 2024, the Company entered into the FHLB Loan pursuant to the Advances and Security Agreement.

The FHLB Loan is a 4.5-year term loan in the principal amount of $ 57.0 million.

The FHLB Loan provides for interest-only payments during its term, with principal due in full at maturity.

The interest rate is fixed over the term of the loan at 4.00 %.

The FHLB Loan is fully secured by a pledge of specific investment securities of HSIC.

The Company used the proceeds to fund redemptions of the draws on its prior credit facility.

Term Loan Facility

During the fourth quarter of 2025, the Company entered into a Term Loan Credit Agreement (the “Term Loan Facility”) with a syndicate of participating banks.

The Term Loan Facility includes (a) an unsecured senior delayed draw term loan facility (“DDTL”) in the aggregate principal amount of $ 150.0 million (the “Tranche A DDTL”) and (b) an additional unsecured senior DDTL in the aggregate principal of $ 150.0 million (the “Tranche B DDTL” and together with the Tranche A DDTL, the “Term Loan Facility”).

The Term Loan Facility was used by the Company to fund a portion of the consideration of the Company’s acquisition of Apollo Group Holdings Limited (“Apollo”) and related transaction fees and expenses.

Amounts drawn under the Term Loan Facility bear interest at either term SOFR plus a margin, which ranges from 150 basis points to 190 basis points, or the base rate plus a margin, which ranges from 50 basis points to 90 basis points, each depending on the Company’s debt to capitalization ratio.

SOFR is calculated using a SOFR floor of 0.00 % and a credit spread adjustment of 0.10 %.

The base rate is the highest of (i) the Agent’s then-current prime lending rate, (ii) the Federal Funds Rate plus 0.50 %, (iii) SOFR plus 1.00 % and (iv) zero percent (0%).

In addition, the Company pays a fee ranging from 0.20 % to 0.35 % on average daily undrawn amounts under the Facility, depending on the Company’s debt to capitalization ratio.

The Tranche A DDTL matures on January 1, 2028 and the Tranche B DDTL matures on July 2, 2029.

On December 30, 2025, the Company drew $ 150 million of the Tranche A DDTL and $ 150 million of the Tranche B DDTL for the acquisition of Apollo on January 1, 2026.

The Term Loan Facility includes customary covenants, including certain limitations on the incurrence by the Company of additional indebtedness exceeding $ 10.0 million and on the Company’s ability to make distributions to its stockholders, or redeem, repurchase or retire shares of stock, upon the occurrence of certain events and certain financial covenants, including financial covenants relating to our minimum consolidated net worth, maximum total debt to capitalization, minimum A.M.

Best rating and minimum liquidity, as well as customary events of default.

As of March 31, 2026, the Company was in compliance with all covenants.

The Term Loan Facility is unsecured.

In connection with the Revolving Credit Facility (defined below), during the fourth quarter of 2025, the Company and the subsidiary guarantors party thereto, entered into a guaranty agreement, pursuant to which the Company’s obligations under the Term Loan Facility are guaranteed by the Company and its existing wholly-owned subsidiaries and subsequently acquired or organized subsidiaries, excluding insurance company subsidiaries and subject to certain other exceptions.

The Company reports debt related to the Term Loan Facility in its March 31, 2026 Condensed Consolidated Balance Sheet, net of debt issuance costs of approximately $ 5.1 million.

These deferred financing costs are presented as a direct deduction from the carrying amount of the debt.

Revolving Credit Facilities

During the fourth quarter of 2025, the Company, entered into a Credit Agreement (the “Revolving Credit Facility”) with a syndicate of participating banks.

The Revolving Credit Facility is unsecured and provided the Company with up to a initial maximum principal amount of $ 150.0 million which was increased to $ 250.0 million on the closing date of the Company’s acquisition of Apollo.

The Company initially drew $ 43.0 million, which was used to redeem the Company’s prior revolving credit facility (described below).

On December 30, 2025, the company drew an additional $ 71.5 million which was used for the consideration paid for the acquisition of Apollo.

The proceeds were used for the acquisition of Apollo on January 1, 2026.

Interest on the Revolving Credit Facility is payable quarterly.

Amounts drawn under the Facility bear interest at either term SOFR plus a margin, which ranges from 150 and 190 basis points, or the base rate plus a margin, which ranges from

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Notes Payable & Subordinated Debt (continued)

50 basis points to 90 basis points, each depending on the Company’s debt to capitalization ratio.

SOFR is calculated using a SOFR floor of 0.00 % and a credit spread adjustment of 0.10 %.

The base rate is the highest of (i) the Agent’s then current prime lending rate, (ii) the Federal Funds Rate plus 0.50 %, (iii) SOFR plus 1.00 % and (iv) zero percent (0%).

In addition, the Company pays a fee ranging from 0.20 % to 0.35 % on average daily undrawn amounts under the Facility, depending on the Company’s debt to capitalization ratio.

The availability period under the Facility will terminate on November 12, 2030.

The Company is subject to covenants on the Revolving Credit Facility based on minimum net worth, maximum debt to capital ratio, minimum A.M.

Best Rating and minimum liquidity, as well as customary events of default.

As of March 31, 2026, the Company was in compliance with all covenants.

In May 2019, the Company entered into an agreement to issue unsecured subordinated notes (the “Notes”) with an aggregate principal amount of $ 20.0 million.

Interest on the Notes is fixed at 7.25 % for the first 8 years and fixed at 8.25 % thereafter.

Early retirement of the debt ahead of 8 year commitment requires all interest payments to be paid in full as well as the return of outstanding principal.

Principal is due at maturity on May 24, 2039 and interest is payable quarterly.

The Notes have junior priority to all previously issued debt.

The Company reports debt related to the Notes in its March 31, 2026 Condensed Consolidated Balance Sheet and its December 31, 2025 Consolidated Balance Sheet, net of debt issuance costs of approximately $ 0.4 million.

These deferred financing costs are presented as a direct deduction from the carrying amount of the subordinated debt.

The Company has two reportable segments, the Skyward Specialty segment and the Apollo segment, through which it offers a broad array of commercial property and casualty products and solutions on a non-admitted (or E&S) and admitted basis, predominantly in the United States.

The Company defines its segment on the basis of the way in which internally reported financial information is regularly reviewed by the Chief Operating Decision Maker (“CODM”) to analyze financial performance, make decisions and allocate resources.

The Company’s CODM is the chief executive officer.

The accounting policies of the segment are the same as those described in Note 1 “Summary of Significant Accounting Policies” of the Company’s Annual Report on Form 10-K for the year ended December 31, 2024.

The CODM assesses performance for the segment and decides how to allocate resources based on gross written premiums by net underwriting division, underwriting income, and income before income taxes that also is reported on the condensed consolidated statements of operations as consolidated income before income taxes.

The measure of segment assets is reported on the balance sheet as total consolidated assets.

Gross written premiums by underwriting division, net underwriting income, and consolidated net income are used to monitor budget versus actual results.

The chief operating decision maker also uses net underwriting income, annualized return on equity and growth in book value per share in competitive analysis by benchmarking to the Company’s competitors.

The competitive analysis along with the monitoring of budgeted versus actual results are used in assessing performance of the segment and in establishing management’s compensation.

The following table presents gross written premiums by underwriting division for the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30, Nine months ended September 30,

The accounting policies of the segments are the same as those used for the preparation of the Company’s consolidated financial statements.

Intersegment business is allocated to the segment accountable for the underwriting results.

The Skyward Specialty segment is made up of nine distinct underwriting divisions, or “continuing business,” and has dedicated underwriting leadership supported by high-quality technical staff with deep experience in their respective niches.

The Apollo segment consists of the operations of Apollo, a Lloyd’s‑based specialty insurance platform acquired by the Company on January 1, 2026, structured around two core divisions that collectively support its underwriting, specialty‑risk, and managing‑agency activities.

Apollo operates within the Lloyd’s of London market, leveraging Lloyd’s global licensing, centralized underwriting infrastructure, and long‑standing distribution networks to access niche and emerging specialty classes across international markets.

The accounting policies of the segments are the same as those described in Note 1 “Summary of Significant Accounting Policies” of the Company’s Annual Report on Form 10-K for the year ended December 31, 2025.

The CODM assesses performance for the segments and allocates resources based primarily on gross written premiums, managed premiums and underwriting contribution.

The Company does not manage assets by segment, with the exception of goodwill and intangible assets.

Investment results, interest expense, amortization expense, corporate expenses and other income and expenses are not allocated to the underwriting segments.

Gross written premiums by underwriting division, managed premiums and underwriting contribution are used to monitor budget versus actual results.

The CODM also uses underwriting contribution in competitive analysis by benchmarking to the Company’s competitors.

The competitive analysis along with the monitoring of budgeted versus actual results are used in assessing performance of the segments and in establishing management’s compensation.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Segments (continued)

The following table presents gross written premiums by underwriting division for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

($ in thousands) 2026 2025

Skyward Specialty Segment

Accident & Health $ 92,009 $ 63,169

Agriculture and Credit (Re)insurance 168,105 17,044 327,525 96,957

Captives 57,914 66,929

Construction & Energy Solutions 66,576 70,309 215,760 222,745

Credit & Surety 64,174 45,028

Energy Solutions 48,866 75,594

Global Agriculture 102,352 80,617

Global Property 34,517 46,686

1 unchanged sentence

Specialty Programs 94,767 62,675

Surety 43,737 34,592 122,272 106,076

Transactional E&S 50,064 52,006

1 unchanged sentence

Exited business 913 2,405

Total Skyward Specialty Segment gross written premiums 581,804 535,326

Apollo Segment

Syndicate 1969 65,008 —

Syndicate 1971 20,892 —

Total Apollo Segment gross written premiums 85,900 —

Total gross written premiums $ 667,704 $ 535,326

The following table sets forth the Apollo segment’s managed premiums for the three months ended March 31, 2026:

Three months ended March 31,

Aligned Syndicates 210,549

Partner Syndicates 89,456

Total managed premiums $ 300,005

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Segment (continued)

The following table presents information about reported segment net underwriting income, significant segment expenses and a reconciliation of net underwriting income to net income for the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30, Nine months ended September 30,

($ in thousands) 2025 2024 2025 2024

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Segments (continued)

Three months ended March 31, 2026 2025

($ in thousands) Skyward Specialty Apollo Total Skyward Specialty Total

Underwriting income

Net earned premiums $ 363,943 $ 70,064 $ 434,007 $ 300,366 $ 300,366

Underwriting fee income — 10,078 10,078 — —

Commission and fee income 1,527 — 1,527 1,976 1,976

3 unchanged sentences

Other operating and general expenses 45,904 14,185 60,089 38,148 38,148

Corporate expenses — — 4,909 — 3,913

Fee‑based service expenses — 4,170 4,170 — —

Total underwriting expenses 325,194 63,904 394,007 269,947 273,860

Net underwriting income $ 38,245 $ 21,037 $ 97,971 $ 69,620

Reconciliation of net underwriting income to net income:

Net underwriting income $ 38,245 $ 21,037 $ 97,971 $ 69,620

Underwriting income $ 40,276 $ 16,238 $ 51,605 $ 32,395 $ 28,482

Reconciliation of underwriting income to net income:

Underwriting income $ 51,605 $ 28,482

Net investment income 27,055 19,422

Net investment gains 3,185 6,750

Other loss ( 236 ) ( 195 ) ( 216 ) ( 202 )

Other income 15 13

Interest expense 7,719 1,834

4 unchanged sentences

Net income $ 49,731 $ 42,058

The following table presents annualized return on equity for the three and nine months ended September 30, 2025 and 2024 and book value per share as of September 30, 2025 and December 31, 2024:

Three months ended September 30, Nine months ended September 30,

2025 2024 2025 2024

Annualized return on equity 19.7 % 19.3 % 19.3 % 19.1 %

September 30, 2025 December 31, 2024

Book value per share $ 23.75 $ 19.79

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

The following table sets forth the Company’s income tax expense and effective tax rates for the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30, Nine months ended September 30,

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

The following table sets forth the Company’s income tax expense and effective tax rates for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

($ in thousands) 2026 2025

1 unchanged sentence

Effective tax rate 19.9 % 18.2 %

The effective tax rate will differ from the statutory rate of 21 percent due to permanent differences for disallowed expenses for tax and beneficial adjustments for tax-exempt income, dividends-received deduction, non-deductible expenses and discrete items.

The effective tax rate for the three and nine months ended September 30, 2025 increased 2.5 % and decreased 0.6 %, respectively, when compared to the same 2024 periods.

The effective tax rate for the three months ended September 30, 2025 was primarily impacted by a permanent tax item related to non-deductible acquisition expenses, which increased the effective tax rate by 1.1 %.

The Company paid income taxes of $ 11.0 million and $ 31.8 million during the three and nine months ended September 30, 2025, respectively, and $ 8.5 million and $ 23.0 million during the three and nine months ended September 30, 2024, respectively.

On July 4, 2025, the One Big Beautiful Bill Act (“OBBBA”) was enacted in the U.S.

The OBBA includes significant provisions, such as the permanent extension of certain expiring provisions of the Tax Cuts and Jobs Act, modifications to the international tax framework and the restoration of favorable tax treatment for certain business provisions.

The legislation has multiple effective dates, with certain provisions effective in 2025 and others implemented through 2027.

These legislative changes did not and are not expected to have a material impact on the Company’s third quarter or future effective tax rates.

The Company has included the estimated impact of the OBBBA in its third quarter financial results, the period of enactment.

The effective tax rate will differ from the statutory rate of 21 percent due to tax charges associated with the effect of foreign operations, permanent differences for disallowed expenses for tax and beneficial adjustments for tax-exempt income, dividends-received deduction, and discrete items.

The effect of foreign operations is primarily related to income of our foreign operations taxed at statutory tax rates of 15 % in Bermuda and 25 % in UK.

The effective tax rate for three months ended March 31, 2026 was impacted by certain discrete tax items, primarily tax benefits from stock-based compensation, which reduced the effective tax rate by 3.1 %.

The Company paid income taxes of $ 2.9 million during the three months ended March 31, 2026.

Losses and Loss Adjustment Expenses

The following table sets forth the reconciliation of unpaid losses and loss adjustment expenses (“LAE”) as reported in the condensed consolidated balance sheets as of and for the nine months ended September 30, 2025 and 2024:

Nine months ended September 30,

Three months ended March 31,

($ in thousands) 2026 2025

15 unchanged sentences

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Commission and Fee Income

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Commission and Fee Income and Underwriting Fee Income

Skyward Underwriters Agency, Inc.

1 unchanged sentence

Commission and fee income is primarily generated from SUA for the placement of insurance policies on either a third-party insurance or reinsurance company.

The following table sets forth the Company’s disaggregated revenues from contracts with customers for the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30, Nine months ended September 30,

The following table sets forth the Company’s disaggregated revenues from contracts with customers for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

($ in thousands) 2026 2025

1 unchanged sentence

SUA fee income 455 1,177

Other ( 525 ) ( 645 ) ( 1,036 ) 335

Total commission and fee income $ 1,904 $ 1,818 $ 6,440 $ 5,897

The Company’s contract assets from commission and fee income as of September 30, 2025 and December 31, 2024 were $ 2.6 million and $ 1.4 million, respectively.

Total commission and fee revenue 3,329 3,024

Commission and fee expenses ( 1,802 ) ( 1,048 )

Net commission and fee income $ 1,527 $ 1,976

The Company’s contract assets from commission and fee income as of March 31, 2026 and December 31, 2025 were $ 0.7 million and $ 1.0 million, respectively.

Through its Apollo subsidiary ASML, the Company earns revenue for services performed in its capacity as managing agent to both its wholly owned and third‑party capitalized Lloyd’s syndicates.

These revenues primarily consist of managing agency fees, which compensate the Company for underwriting oversight, operational administration, and regulatory and compliance support, as well as profit commission, which is contingent upon the underwriting performance of certain syndicates.

ASML receives managing agency fees from managed syndicates, including 1969, 1971 and 1972 (collectively the “Managed Syndicates”) at a rate of 0.9 % of the managed stamp capacity and for SPA1925 at 1.0 %, which is fully recognized over the period the services are rendered.

ASML receives profit commission at a rate of 17.5 % for Syndicate 1969 and 20.0 % for Syndicate 1971, subject to a two-year deficit clause.

No profit commission has been recognized for SPA1925 or Syndicate 1972.

ASML also receives a share of the leader’s fee for managing consortium arrangements.

Managing agency fees and services revenue are recognized over time as services are rendered, while profit commission is recognized only when it becomes probable that no significant reversal will occur.

This revenue is disclosed in underwriting fee income.

The following table sets forth the Apollo’s revenues from contracts with customers for the three months ended March 31, 2026:

Three months ended March 31,

($ in thousands) 2026

Managing agents fees $ 3,527

Profit commission & consortium overrider charged to Managed Syndicates 6,551

Underwriting fee income $ 10,078

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Underwriting, Acquisition and Insurance Expenses

The following table sets forth the components of underwriting, acquisition and insurance expenses for the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30, Nine months ended September 30,

The following table sets forth the components of underwriting, acquisition and insurance expenses for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

($ in thousands) 2026 2025

1 unchanged sentence

Other operating and general expenses 60,089 38,148

Corporate expenses 4,909 3,913

Total underwriting, acquisition and insurance expenses $ 124,614 $ 86,551

2 unchanged sentences

The Company remains obligated for amounts ceded in the event that the reinsurers do not meet their obligations.

The following tables set forth the effects of reinsurance on written and earned premiums and losses and loss adjustment expenses for the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30,

($ in thousands) Written Earned Written Earned

Direct premiums $ 414,475 $ 417,896 $ 347,444 $ 349,980

Assumed premiums 192,034 117,008 52,570 69,436

Ceded premiums ( 165,342 ) ( 183,107 ) ( 131,692 ) ( 149,859 )

Net premiums $ 441,167 $ 351,797 $ 268,322 $ 269,557

Ceded losses and LAE incurred $ 126,632 $ 108,152

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Reinsurance (continued)

Nine months ended September 30,

The following tables set forth the effects of reinsurance on written and earned premiums and losses and loss adjustment expenses for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

($ in thousands) Written Earned Written Earned

4 unchanged sentences

Ceded losses and LAE incurred $ 152,573 $ 135,467

The following table sets forth the components of reinsurance recoverables and ceded unearned premium as of September 30, 2025 and December 31, 2024:

($ in thousands) September 30, 2025 December 31, 2024

The following table sets forth the components of reinsurance recoverables and ceded unearned premium as of March 31, 2026 and December 31, 2025:

($ in thousands) March 31, 2026 December 31, 2025

Ceded unpaid losses and LAE $ 1,109,909 $ 921,165

Ceded paid losses and LAE 229,323 201,010

Loss portfolio transfer — 22,662

Allowance for credit losses ( 2,295 ) ( 2,295 )

3 unchanged sentences

These trust accounts provide the Company additional security to collect claim recoverables under reinsurance contracts and the Company does not carry these on the balance sheet because the Company will only have custody over these accounts upon the failure of the reinsurer to pay amounts due.

At September 30, 2025, the market value of these accounts was approximately $ 220.4 million.

At March 31, 2026, the market value of these accounts was approximately $ 250.7 million.

The trust amount will be adjusted periodically, by mutual agreement, based on claim payments and loss reserve recoverables.

Certain ceded reinsurance contracts that transfer only significant timing risk and do not transfer sufficient underwriting risk are accounted for using the deposit method of accounting.

The Company’s deposit asset at September 30, 2025 and December 31, 2024 was $ 22.0 million and $ 25.9 million, respectively, and was included in other assets on the condensed consolidated balance sheets.

The Company’s deposit asset at March 31, 2026 and December 31, 2025 was $ 18.2 million and $ 22.7 million, respectively, and was included in other assets on the condensed consolidated balance sheets.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO UNAUDITED CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Earnings Per Share

The following table sets forth the computation of basic and diluted net earnings per share for the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30, Nine months ended September 30,

The following table sets forth the computation of basic and diluted net earnings per share for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

($ in thousands, except for share and per share amounts) 2026 2025

6 unchanged sentences

Diluted earnings per share $ 1.09 $ 1.01

The following table presents anti-dilutive instruments that were excluded from the calculation of diluted weighted-average common share equivalents during the three and nine months ended September 30, 2025 and 2024:

Three months ended September 30, Nine months ended September 30,

2025 2024 2025 2024

The following table presents anti-dilutive instruments that were excluded from the calculation of diluted weighted-average common share equivalents during the three months ended March 31, 2026 and 2025:

Three months ended March 31,

Stock units 385,108 56,155

4 unchanged sentences

The Company holds a 20 % ownership interest in RISCOM.

Net earned premium and gross commission expense related to these agreements for the three and nine months ended September 30, 2025 and 2024 were as follows:

Three months ended September 30, Nine months ended September 30,

Net earned premium and gross commission expense related to these agreements for the three months ended March 31, 2026 and 2025 were as follows:

Three months ended March 31,

($ in thousands) 2026 2025

1 unchanged sentence

Commissions 8,188 7,632

Premiums receivable as of September 30, 2025 and December 31, 2024 were $ 15.2 million and $ 12.6 million, respectively.

Advisory and professional services fees and expense reimbursements paid to various affiliated stockholders and directors for the three and nine months ended September 30, 2025 were $ 0.2 million and $ 0.5 million, compared to $ 0.2 million and $ 0.4 million for the three and nine months ended September 30, 2024.

Premiums receivable as of March 31, 2026 and December 31, 2025 were $ 18.4 million and $ 13.9 million, respectively.

Advisory and professional services fees and expense reimbursements paid to various affiliated stockholders and directors for the three months ended March 31, 2026 and 2025 were $ 0.2 million.

See Note 6 for investments involving affiliated companies and additional related party transactions.

On January 1, 2026 (the “Acquisition Date”), the Company completed the acquisition of Apollo Group Holdings Limited (“Apollo”) pursuant to the Apollo share purchase agreements and acquired 100 % of the issued and outstanding share capital of Apollo.

Apollo is a U.K.-based specialty underwriting platform operating at Lloyd’s of London.

Apollo underwrites a multi-class specialty insurance portfolio and offers products across Property, Casualty, Marine, Energy & Transportation, Specialty and Reinsurance, as well as digital and embedded risk programs.

The Company acquired Apollo

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Acquisitions (continued)

to broaden its specialty insurance platform, expand into additional specialty niches, enhance its innovation and technology capabilities, and strengthen its market position.

The fair value of the consideration transferred, or the purchase price, is approximately $ 559.1 million.

This amount is based on (i) the issuance of 3,679,332 shares of common stock of the Company, using the closing price of Skyward common stock of $ 51.11 per share on December 31, 2025, the last trading day prior to the Acquisition Date, and (ii) $ 371.1 million in cash (the “Cash Consideration”).

The table below presents the components of the fair value of consideration transferred:

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

Share consideration

Skyward Specialty Insurance Group, Inc.

common stock issued to existing Apollo common stockholders 3,679,332

Skyward Specialty Insurance Group, Inc.

closing stock price on December 31, 2025 $ 51.11

Consideration of Skyward Specialty Insurance Group, Inc.

issued common stock $ 188,051

Cash consideration 371,089

Total consideration $ 559,140

The Company accounted for the transaction as a business combination under ASC 805, Business Combinations (“ASC 805”).

The purchase price has been preliminarily allocated to the assets acquired and liabilities assumed based on their estimated fair values as of the Acquisition Date.

The Company is considered the accounting acquirer in the transaction.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Acquisitions (continued)

The following table summarizes the preliminary purchase price allocation as of the Acquisition Date:

($ in thousands) January 1, 2026

Assets acquired, excluding goodwill

Fixed maturity securities, available-for-sale, at fair value $ 222,460

Short-term investments, at fair value 187,178

Cash and cash equivalents 68,054

Funds at Lloyd's 106,336

Premiums receivable, net 272,803

Reinsurance recoverables, net 165,540

Ceded unearned premium 69,097

Deferred policy acquisition costs and VOBA 56,128

Deferred income taxes 13,966

Intangible assets, excluding goodwill, net 262,000

Other assets 25,830

Total assets acquired, excluding goodwill 1,449,392

Liabilities assumed

Reserves for losses and loss adjustment expenses 477,596

Unearned premiums 233,501

Reinsurance and premium payables 144,536

Funds held for others 18,684

Accounts payable and accrued liabilities 71,506

Deferred income taxes 69,837

Total liabilities assumed 1,015,660

Fair value of net assets acquired, excluding goodwill 433,732

Total consideration $ 559,140

Preliminary allocation to goodwill $ 125,408

The Apollo acquisition was accounted for as a business combination using the acquisition method of accounting in accordance with ASC 805.

The purchase price was allocated to assets acquired and liabilities assumed based on the estimated fair values at the Acquisition Date.

Goodwill recognized in the transaction represents the excess of consideration transferred over the fair value of identifiable net assets acquired and will not be deductible for tax purposes and is fully allocated to the U.K.

Goodwill primarily represents the expected future economic benefits arising from the acquisition, including anticipated synergies from the integration of operations, Apollo’s established specialty underwriting platform, and access to its distribution network and Lloyd’s market presence.

The identifiable intangible assets primarily relate to syndicate capacity, cover holder relationships, strategic partner syndicates and trade names.

The amounts, based on preliminary valuations and subject to final adjustment, allocated to intangible assets are as follows:

($ in thousands) Estimated fair value Estimated average useful life (in years) Estimated Annual Amortization Expense

Syndicate 1969 capacity - with fees $ 90,000 Indefinite N/A, indefinite lived asset

Syndicate 1971 capacity - with fees 110,000 Indefinite N/A, indefinite lived asset

Cover holder relationships 25,000 7 $ 3,571

Strategic partner syndicates 2,000 5 400

Trade name 35,000 10 3,500

Total $ 262,000 $ 7,471

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Acquisitions (continued)

The Company also recognized value of business acquired (“VOBA”), which represents the estimated fair value of the deferred acquisition costs of acquired in‑force insurance contracts.

VOBA is amortized over one year, reflecting the expected runoff of the acquired in‑force contracts.

VOBA is aggregated with deferred policy acquisition costs and included within deferred policy acquisition costs and VOBA on the consolidated balance sheets.

For the three months ended March 31, 2026 the Company recognized $ 7.3 million and $ 6.7 million in underwriting, acquisition and insurance expenses and amortization expense, respectively, on the consolidated statements of operations related to the amortization of VOBA .

Estimated fair values of assets acquired and liabilities assumed from Apollo are subject to change as additional information is obtained, and will be updated and finalized within the measurement period that will not extend beyond 12 months from the Acquisition Date.

Any measurement period adjustments will be recorded in the period in which the adjustments are identified, as if they had been recognized as of the acquisition date.

The results of operations for Apollo of $ 80.1 million of revenue and $ 22.2 million of net income from the date of the acquisition to the period ended March 31, 2026, have been included within the accompanying consolidated statements of operations and comprehensive loss.

All transaction expenses incurred by the Company were expensed as incurred and reflected in the Company’s results of operations for the period ended December 31, 2025 in accordance with ASC 805.

No material transaction expenses were incurred for the period ended March 31, 2026.

The Company has not presented the unaudited supplemental pro forma financial information required by ASC 805-10-50-2(h) as it is impractical to do so, as Apollo did not historically prepare quarterly financial statements and its historical financial information was prepared under U.K.

GAAP rather than U.S.

Commitments and Contingencies

Apollo Acquisition

On September 2, 2025, the Company entered into two share purchase agreements (the "Apollo Majority SPAs") with institutional and management shareholders, respectively, of Apollo Group Holdings Limited ("Apollo") (the "Majority Sellers").

Pursuant to the Apollo Majority SPAs, in accordance with the terms and subject to the conditions therein, the Company has agreed to acquire all of the issued shares of Apollo held by the Majority Sellers, representing approximately 87 % of the issued share capital of Apollo.

In addition, the closing of the transaction ("completion") is conditioned upon the Company acquiring 100 % of the issued share capital of Apollo at completion pursuant to additional short-form share purchase agreements (the "Apollo Minority SPAs" and together with the Apollo Majority SPAs, the "Apollo SPAs") to be entered into either prior to or at completion with the remaining minority shareholders of Apollo (the "Minority Sellers" and together with the Majority Sellers, the "Sellers").

The consideration for the entire issued share capital of Apollo under the Apollo SPAs is $ 555.0 million, approximately 33 % of which will be satisfied by the issuance of 3,679,332 unregistered shares of common stock of the Company to certain Sellers and the remainder in cash.

The acquisition is expected to close in the first quarter of 2026, subject to the satisfaction of closing conditions, including regulatory approvals.

In connection with the Apollo SPAs, on September 2, 2025, the Company entered into debt commitment letters (the "Apollo Commitment Letters") pursuant to which Barclays Bank PLC (the "Lender") has committed to provide us with debt financing in the form of (i) up to two senior unsecured delayed draw term loan credit facilities of up to $ 300.0 million in total, and (ii) in case the borrower is not able to obtain consent from lenders under its existing revolving credit agreement to the transactions under the Apollo SPAs, a senior unsecured bridge facility of up to $ 150.0 million, in each case, on the terms and subject to the conditions set forth in the Apollo Commitment Letters.

The Company is named as a defendant in various legal actions arising from claims made under insurance policies and contracts.

The Company is named as a party in various legal actions arising from claims made under insurance policies and contracts.

Those actions are considered by the Company in estimating the losses and loss adjustment expense reserves.

9 unchanged sentences

Compared sentence by sentence after normalising whitespace, quotation marks, case and digits, so re-formatting and restated figures do not read as changed language. Wording changes appear as one removal and one addition. The current filing and the prior one are authoritative.

What changed 10-Q

Item 1. Financial Statements