Skyward Specialty (SKWD) director Ashe sells 740 shares to cover RSU tax bill

Rhea-AI Filing Summary

Skyward Specialty Insurance Group director Gena L. Ashe reported RSU vesting and related share sales. On May 11, 2026, 1,797 Restricted Stock Units from a 2025 award converted into an equal number of common shares. To cover taxes and fees from this vesting, Ashe sold 740 common shares in open-market transactions at $46.35 per share. Following these transactions, Ashe directly holds 4,570 shares of common stock, reflecting a net increase in ownership from the RSU award.

Insights

Equity compensation analyst

Routine RSU vesting with tax-cover sales; limited signaling value.

The filing shows director Gena L. Ashe had 1,797 RSUs from a 2025 award vest into common stock, with each RSU settling into one share. This is standard equity compensation rather than a discretionary market purchase.

To handle tax obligations from the vesting and settlement, Ashe sold 740 common shares at $46.35 per share in open-market transactions, as described in the footnotes. The issuer delayed settlement so these sales occurred during an open trading window, underscoring their administrative nature.

After the transactions, Ashe directly holds 4,570 common shares, and no remaining derivative position from this RSU award is reported. Overall, this pattern—RSU vesting plus partial sale to fund taxes—is typical and carries modest informational content for investors.

Insider Trade Summary

Net Seller: 740 shares ($34,299)

Net Sell 5 txns

Insider Ashe Gena L

Role null

Sold 740 shs ($34K)

Type	Security	Shares	Price	Value
Exercise	2025 RSU Award	1,797	$0.00	--
Exercise	Common Stock	1,797	$0.00	--
Sale	Common Stock	100	$46.35	$5K
Sale	Common Stock	140	$46.35	$6K
Sale	Common Stock	500	$46.35	$23K

Holdings After Transaction: 2025 RSU Award — 0 shares (Direct, null); Common Stock — 5,310 shares (Direct, null)

Footnotes (1)

1. Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock. Sales to cover taxes and fees incurred in connection with the vesting and settlement of the Reporting Person's RSUs reported on this Form 4. On May 7, 2025, the Reporting Person was granted an RSU Award in the amount of 1,797 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 7, 2026. The Reporting Person elected to sell shares to cover the associated tax liability incurred due to the vesting and settlement of the RSUs reported on this Form 4.The Issuer delayed the settlement, pursuant to the terms of the RSU Award Agreement, so that the sales to cover the tax liability occurred during an open trading window.

Key Figures

Shares sold: 740 shares Sale price: $46.35 per share RSUs vested: 1,797 RSUs +2 more

5 metrics

Shares sold 740 shares Open-market sales on May 11, 2026 at $46.35

Sale price $46.35 per share Price for 740 common shares sold

RSUs vested 1,797 RSUs 2025 RSU Award fully vested on May 7, 2026

Post-transaction holdings 4,570 shares Common stock directly owned after transactions

RSU-to-share ratio 1 RSU : 1 share Each RSU settles for one share of common stock

Key Terms

Restricted Stock Unit ("RSU"), vesting and settlement, tax liability, open trading window, +1 more

5 terms

Restricted Stock Unit ("RSU") financial

"Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock."

vesting and settlement financial

"Sales to cover taxes and fees incurred in connection with the vesting and settlement of the Reporting Person's RSUs"

tax liability financial

"elected to sell shares to cover the associated tax liability incurred due to the vesting and settlement of the RSUs"

open trading window financial

"settlement ... so that the sales to cover the tax liability occurred during an open trading window"

A designated period when company executives, directors and certain employees are permitted to buy or sell their employer’s stock under the company’s trading policy because material information has been disclosed. Think of it like scheduled store hours after a big delivery: it reduces the risk of trading on secret information, and investors watch insider activity during these windows as a signal of how those closest to the business view its prospects.

derivative exercise/conversion financial

"transaction_action": "derivative exercise/conversion""

Form 4 Insider Transactions: What Each Field Means →

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)
05/11/2026

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	05/11/2026		M		1,797	A	(1)	5,310	D
Common Stock	05/11/2026		S(2)		100	D	$46.35	5,210	D
Common Stock	05/11/2026		S(2)		140	D	$46.35	5,070	D
Common Stock	05/11/2026		S(2)		500	D	$46.35	4,570	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
2025 RSU Award	(1)	05/11/2026		M			1,797	(3)(4)	(3)(4)	Common Stock	1,797	$0	0	D

Explanation of Responses:

1. Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock.

2. Sales to cover taxes and fees incurred in connection with the vesting and settlement of the Reporting Person's RSUs reported on this Form 4.

3. On May 7, 2025, the Reporting Person was granted an RSU Award in the amount of 1,797 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 7, 2026.

4. The Reporting Person elected to sell shares to cover the associated tax liability incurred due to the vesting and settlement of the RSUs reported on this Form 4.The Issuer delayed the settlement, pursuant to the terms of the RSU Award Agreement, so that the sales to cover the tax liability occurred during an open trading window.

	/s/ Stacy E. Skelton, Attorney-in-Fact	05/12/2026
	** 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)

FAQ

What did Skyward Specialty (SKWD) director Gena L. Ashe report in this Form 4?

Gena L. Ashe reported the vesting of 1,797 Restricted Stock Units into common stock and the related sale of 740 shares. The sales were executed at $46.35 per share to cover taxes and fees arising from the RSU vesting and settlement.

How many Skyward Specialty (SKWD) shares did Gena L. Ashe sell and at what price?

Ashe sold a total of 740 shares of Skyward Specialty common stock in open-market transactions at $46.35 per share. According to the footnotes, these sales were specifically to cover tax liabilities and fees from the RSU vesting and settlement.

What RSU award is involved in Gena L. Ashe’s Skyward Specialty (SKWD) filing?

The filing involves a 2025 RSU Award of 1,797 Restricted Stock Units granted on May 7, 2025. Subject to the RSU Agreement’s terms, the award fully vested on May 7, 2026, with each RSU settling into one share of common stock.

Why did Gena L. Ashe sell Skyward Specialty (SKWD) shares after her RSUs vested?

Footnotes explain Ashe elected to sell shares to cover tax liability and related fees triggered by the RSU vesting and settlement. The issuer delayed settlement so these tax-cover sales occurred during an open trading window, indicating an administrative rather than strategic sale.

How many Skyward Specialty (SKWD) shares does Gena L. Ashe hold after these transactions?

Following the RSU conversion and related sales, Ashe directly holds 4,570 shares of Skyward Specialty common stock. This post-transaction balance reflects a net increase in ownership due to the 1,797 RSUs vesting and only 740 shares being sold to cover taxes.

Do these Skyward Specialty (SKWD) transactions indicate any remaining RSU position for Gena L. Ashe?

The data show 1,797 RSUs from the 2025 award fully vested and converted into common stock, with derivative holdings reported as zero for that award. No remaining derivative position from this specific RSU grant is indicated in the filing’s derivative summary.