8-K filed January 6, 2026, 6:59 PM ET ticker SKWD CIK 0001519449

M&A confidence high sentiment positive materiality 0.85

Skyward Specialty closes $555M acquisition of Apollo, financed with $300M debt facility

Skyward Specialty Insurance Group, Inc.

Total consideration $555M: $371M cash plus 3,679,332 shares of SKWD common stock.
Closed Jan 1, 2026; cash portion funded by new $300M unsecured term loan facility (Tranche A $150M, matures Jan 2028; Tranche B $150M, matures Jul 2029).
Apollo is now a wholly owned subsidiary; acquisition expands Skyward's specialty insurance capabilities.
Credit agreement includes covenants on minimum net worth, max debt-to-capitalization, and minimum A.M. Best rating.

item 1.01 item 2.01 item 2.03 item 3.02 item 9.01

Machine-readable event card

schema_version: secwatch.filing_event.v1
accession: 0001519449-26-000002
form_type: 8-K
ticker: SKWD
cik: 0001519449
company_name: Skyward Specialty Insurance Group, Inc.
filed_at: 2026-01-06T23:59:59+00:00
discovered_at: 2026-05-14T18:02:35.302835+00:00
generated_at: 2026-05-16T11:31:59.556831+00:00
sec_items: ["1.01", "2.01", "2.03", "3.02", "9.01"]
event_type: m_and_a
sentiment: positive
materiality_score: 0.85
calibrated_materiality_score: 0.85
confidence: high
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edgar_primary_document_url: https://www.sec.gov/Archives/edgar/data/1519449/000151944926000002/skwd-20260106.htm
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Source-grounded claims

c89c0a2789926d6ce72ed2bf0597bdc390031d59

Skyward Specialty Insurance Group, Inc. incurred credit facility of unsecured senior delayed draw term loan facility in the aggregate principal amount of $150.0 million (the "Tranche A Ter with Barclays Bank PLC, as Administrative Agent at term SOFR plus a margin, which will range from 150 basis points to 190 basis poi maturing Tranche A Term Facility matures on January 1, 2028 and the Tranche B Term Facility matures on July 2, 2029.

and co-syndication agents for the Tranche B Term Facility. The facility includes (a) an unsecured senior delayed draw term loan facility in the aggregate principal amount of $150.0 million (the “Tranche A Term Facility”) and (b) an additional unsecured senior delayed draw term loan facility in the aggregate principal of $150.0 million (the “Tranche B Term Facility”

SEC 8-K Item 2.03/2.04 confidence 1.0 SEC evidence

22b16db50da3cd769ae68c5f8529964a5e3983b3

Skyward Specialty Insurance Group, Inc. completed an acquisition involving Sellers (Majority Sellers and Minority Sellers of Apollo Group Holdings Limited) for $555.0 million (closed 2026-01-01).

Sellers" and together with the Majority Sellers, the "Sellers"). The consideration for the entire issued share capital of Apollo (the "Apollo Shares") under the Apollo SPAs is $555.0 million. On January 1, 2026 (the “Closing Date”), the Company consummated the Acquisition and related transactions pursuant to the Apollo SPAs (the “Closing”). hares") under the Apollo

SEC 8-K Item 2.01/5.01 confidence 0.9 SEC evidence

3bc1b1fdf85f5b5fa2d4264f677d8dadb5eb83cd

Skyward Specialty Insurance Group, Inc. entered into Guaranty Agreement with subsidiary guarantors (effective 2025-12-30).

In connection with the Credit Agreement, on December 30, 2025, the Company and the subsidiary guarantors party thereto, entered into a Guaranty Agreement (the “Guaranty Agreement”), pursuant to which the Company’s obligations under the Facility are guaranteed by the Company and its existing wholly-owned subsidiaries and subsequently acquired or organized subsidiaries

SEC 8-K Item 1.01/1.02 confidence 0.9 SEC evidence

44e0eda400044e19d1060f9052bee8cb07a221ec

Skyward Specialty Insurance Group, Inc. entered into Term Loan Credit Agreement with Barclays Bank PLC, Truist Securities, Inc., Citizens Bank, N.A., Texas Capital Bank valued at $300.0 million (effective 2025-12-30).

On December 30, 2025, the Company entered into a Term Loan Credit Agreement (the “Facility”) by and among the Company, as Borrower, the lenders from time to time parties thereto (each a “Lender” and collectively, the “Lenders”), Barclays Bank PLC, as Administrative Agent (the “Agent”), and the Agent, Truist Securities, Inc., Citizens Bank, N.A. and Texas Capital Bank as joint lead arrangers, joint book runners and co-syndication agents for the Tranche B Term Facility.

SEC 8-K Item 1.01/1.02 confidence 0.9 SEC evidence

ab514a73a02e41c5c4d1dc401bcef339af30430d

Skyward Specialty Insurance Group, Inc. amended First Amendment with Barclays Bank PLC (effective 2025-12-30).

On December 30, 2025, the Company entered into the First Amendment (the “Amendment”) to the Credit Agreement, dated November 13, 2025 (the “Existing Credit Agreement”), by and among the Company, the guarantors party thereto, the lenders party thereto and Barclays Bank PLC, as administrative agent.

SEC 8-K Item 1.01/1.02 confidence 0.9 SEC evidence

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and co-syndication agents for the Tranche B Term Facility. The facility includes (a) an unsecured senior delayed draw term loan facility in the aggregate principal amount of $150.0 million (the “Tranche A Term Facility”) and (b) an additional unsecured senior delayed draw term loan facility in the aggregate principal of $150.0 million (the “Tranche B Term Facility”

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and co-syndication agents for the Tranche B Term Facility. The facility includes (a) an unsecured senior delayed draw term loan facility in the aggregate principal amount of $150.0 million (the “Tranche A Term Facility”) and (b) an additional unsecured senior delayed draw term loan facility in the aggregate principal of $150.0 million (the “Tranche B Term Facility”

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and co-syndication agents for the Tranche B Term Facility. The facility includes (a) an unsecured senior delayed draw term loan facility in the aggregate principal amount of $150.0 million (the “Tranche A Term Facility”) and (b) an additional unsecured senior delayed draw term loan facility in the aggregate principal of $150.0 million (the “Tranche B Term Facility”

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Sellers" and together with the Majority Sellers, the "Sellers"). The consideration for the entire issued share capital of Apollo (the "Apollo Shares") under the Apollo SPAs is $555.0 million. On January 1, 2026 (the “Closing Date”), the Company consummated the Acquisition and related transactions pursuant to the Apollo SPAs (the “Closing”). hares") under the Apollo

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Sellers" and together with the Majority Sellers, the "Sellers"). The consideration for the entire issued share capital of Apollo (the "Apollo Shares") under the Apollo SPAs is $555.0 million. On January 1, 2026 (the “Closing Date”), the Company consummated the Acquisition and related transactions pursuant to the Apollo SPAs (the “Closing”). hares") under the Apollo

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and co-syndication agents for the Tranche B Term Facility. The facility includes (a) an unsecured senior delayed draw term loan facility in the aggregate principal amount of $150.0 million (the “Tranche A Term Facility”) and (b) an additional unsecured senior delayed draw term loan facility in the aggregate principal of $150.0 million (the “Tranche B Term Facility”

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Sellers" and together with the Majority Sellers, the "Sellers"). The consideration for the entire issued share capital of Apollo (the "Apollo Shares") under the Apollo SPAs is $555.0 million. On January 1, 2026 (the “Closing Date”), the Company consummated the Acquisition and related transactions pursuant to the Apollo SPAs (the “Closing”). hares") under the Apollo

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Source: SEC EDGAR

accession 0001519449-26-000002

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