Skyward Specialty director awarded 3,334 RSUs

Ashe Gena L reported acquisition or exercise transactions in this Form 4 filing.

Rhea-AI Filing Summary

Ashe Gena L reported acquisition or exercise transactions in this Form 4 filing.

Skyward Specialty Insurance Group director Gena L. Ashe reported a new equity grant. On May 6, 2026, she received a 2026 RSU Award covering 3,334 restricted stock units (RSUs), each representing the right to receive one share of common stock after vesting and settlement.

The grant will fully vest on the date of Skyward Specialty’s 2027 Annual Meeting of Shareholders, subject to the award’s terms. Following the reported transactions, Ashe directly holds 3,513 shares of common stock, in addition to the new RSU award.

Insider Trade Summary

Grant/Award: 3,334 shares

Grant/Award 2 txns

Insider Ashe Gena L

Role Director

Type	Security	Shares	Price	Value
Grant/Award	2026 RSU Award	3,334	$0.00	$0.00
holding	Common Stock	--	--	--

Holdings After Transaction: 2026 RSU Award — 3,334 contracts (Direct); Common Stock — 3,513 shares (Direct)

Footnotes (2)

1. F1. Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.
2. F2. On May 6, 2026, the Reporting Person was granted an RSU Award in the amount of 3,334 RSUs. Subject to the terms of the award agreement, this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders.

Key Figures

RSU grant size: 3,334 RSUs Common shares held: 3,513 shares Vesting event: 2027 Annual Meeting of Shareholders +1 more

4 metrics

RSU grant size 3,334 RSUs 2026 RSU Award granted on May 6, 2026

Common shares held 3,513 shares Direct common stock holdings after reported transactions

Vesting event 2027 Annual Meeting of Shareholders Date when the 2026 RSU Award fully vests, subject to terms

Transaction type Grant/award acquisition Form 4 code A for 3,334 RSUs to director Gena L. Ashe

Key Terms

RSU, RSU Award, Annual Meeting of Shareholders

3 terms

RSU financial

"Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock"

Restricted stock units (RSUs) are a form of company shares given to employees as part of their compensation, usually with certain restrictions or conditions, such as remaining with the company for a set period. When these restrictions lift, employees receive actual shares that they can sell or hold. For investors, RSUs can impact a company's stock supply and reflect the company's commitment to attracting and retaining talent.

RSU Award financial

"On May 6, 2026, the Reporting Person was granted an RSU Award in the amount of 3,334 RSUs"

Annual Meeting of Shareholders financial

"this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders"

A yearly gathering where a company’s owners (shareholders) vote on key items like electing the board, approving executive pay, and ratifying auditors, and receive updates on performance and strategy. Think of it as an annual town hall for owners: it matters to investors because outcomes and disclosures can affect leadership, corporate direction, dividend and governance policies, and therefore the company’s risk and potential return.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transaction did Skyward Specialty (SKWD) report for Gena L. Ashe?

Skyward Specialty reported that director Gena L. Ashe received a 2026 RSU Award covering 3,334 RSUs on May 6, 2026. This is a stock-based compensation grant, not an open-market purchase or sale of existing shares.

How many RSUs were granted to the Skyward Specialty (SKWD) director?

The director received 3,334 restricted stock units (RSUs) as a 2026 RSU Award. Each RSU represents the right to receive one share of Skyward Specialty common stock after vesting and settlement, aligning director compensation with shareholder interests over time.

When do Gena L. Ashe’s RSUs in Skyward Specialty (SKWD) vest?

The 3,334 RSUs granted to Gena L. Ashe will fully vest on the date of Skyward Specialty’s 2027 Annual Meeting of Shareholders. Vesting is subject to the terms of the award agreement governing this director equity grant.

What does each RSU in Skyward Specialty’s 2026 award represent?

Each RSU in the 2026 RSU Award represents the right to receive, after vesting and upon settlement, one share of Skyward Specialty common stock. This structure ties the director’s potential future value directly to the company’s share performance.

How many Skyward Specialty (SKWD) common shares does Gena L. Ashe hold after this filing?

After the reported transactions, Gena L. Ashe directly holds 3,513 shares of Skyward Specialty common stock. These share holdings are separate from the 3,334 RSUs, which may convert into additional shares after vesting and settlement.

Was this Skyward Specialty (SKWD) Form 4 a market buy or sell by the director?

No market buy or sell is reported. The Form 4 shows a grant/award acquisition of 3,334 RSUs to director Gena L. Ashe as compensation, plus a holding entry for 3,513 common shares already owned directly.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 05/08/2026 - 04:22 PM Learn about SEC filing dates

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Ashe Gena L

(Last) (First) (Middle)

800 GESSNER

SUITE 600

(Street)

HOUSTON TEXAS 77024

(City) (State) (Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Skyward Specialty Insurance Group, Inc. [ SKWD ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
	Officer (give title below)		Other (specify below)

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/06/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock								3,513	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
2026 RSU Award	(1)	05/06/2026		A		3,334		(2)	(2)	Common Stock	3,334	$0	3,334	D

Explanation of Responses:

1. Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.

2. On May 6, 2026, the Reporting Person was granted an RSU Award in the amount of 3,334 RSUs. Subject to the terms of the award agreement, this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders.

	/s/ Stacy E. Skelton, Attorney-in-Fact	05/08/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)