Skyward EVP settles PSUs, shares withheld for tax

Skyward Specialty Insurance Group EVP Sean W. Duffy reported equity compensation activity tied to performance share awards.

Rhea-AI Filing Summary

Skyward Specialty Insurance Group EVP Sean W. Duffy reported equity compensation activity tied to performance share awards. On May 6, 2026, 2,861 Performance Share Units (PSUs) granted on February 27, 2023, fully vested based on performance from January 1, 2023 through December 31, 2025 and were settled in an equal number of common shares.

To cover related tax withholding obligations, 1,671 common shares were withheld, a disposition that the company mandated and that was not a discretionary market transaction. After these transactions, Duffy directly held 20,097 shares of Skyward Specialty Insurance Group common stock.

Insider Trade Summary

2,861 shares exercised/converted

Exercise 3 txns

Insider Duffy Sean W

Role EVP & Chief Claims Officer

Type	Security	Shares	Price	Value
Exercise	2023 LTIP - PSUs	2,861	$0.00	$0.00
Exercise	Common Stock	3,805	$0.00	$0.00
Exercise Price or Tax Liability	Common Stock	1,671	$43.68	$73K

Holdings After Transaction: 2023 LTIP - PSUs — 0 contracts (Direct); Common Stock — 20,097 shares (Direct)

Footnotes (4)

1. F1. Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Performance Share Units ("PSUs") listed in Line I of Table II.
2. F2. The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the PSUs listed in Line I of Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.
3. F3. Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.
4. F4. On February 27, 2023, the Reporting Person was awarded 2,861 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors.

Key Figures

PSUs converted to common stock: 2,861 units Shares withheld for taxes: 1,671 shares at $43.68 Post-transaction share holdings: 21,768 shares +2 more

5 metrics

PSUs converted to common stock 2,861 units 2023 PSUs covering performance from January 1, 2023 to December 31, 2025

Shares withheld for taxes 1,671 shares at $43.68 Common stock withheld on May 6, 2026 to cover tax obligations on PSU vesting

Post-transaction share holdings 21,768 shares Direct ownership of Skyward Specialty common stock after May 6, 2026 transactions

Original PSU award size 2,861 PSUs Awarded on February 27, 2023 under 2023 LTIP with performance-based vesting

PSU vesting range 0%–150% Potential vesting outcome of 2023 PSUs based on performance over 2023–2025 period

Key Terms

Performance Share Units ("PSUs"), tax withholding obligations, vesting and settlement, Compensation Committee of the Board of Directors, +1 more

5 terms

Performance Share Units ("PSUs") financial

"Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Performance Share Units ("PSUs")"

tax withholding obligations financial

"shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the PSUs"

vesting and settlement financial

"in connection with the vesting and settlement of the PSUs listed in Line I of Table II"

Compensation Committee of the Board of Directors financial

"settled upon certification by the Compensation Committee of the Board of Directors"

2023 LTIP - PSUs financial

"security_title": "2023 LTIP - PSUs""

FAQ

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

What insider transactions did SKWD executive Sean W. Duffy report on this Form 4?

Sean W. Duffy reported PSU vesting and tax withholding. 2,861 Performance Share Units converted into common shares, and 1,671 shares were withheld to satisfy tax obligations. These events reflect equity compensation settlement rather than an open-market stock trade.

Were the SKWD Form 4 share dispositions by Sean W. Duffy open-market sales?

No, the disposition was for tax withholding. The 1,671 shares reported as disposed were withheld by the company to cover tax obligations tied to PSU vesting. The footnote states this withholding was mandated and not a discretionary transaction by Duffy.

How many Skyward Specialty (SKWD) shares does Sean W. Duffy hold after these transactions?

Sean W. Duffy holds 21,768 common shares after the transactions. This post-transaction balance reflects the vesting and settlement of PSUs and the related tax withholding, as reported in the Form 4 totals following the May 6, 2026 entries.

What are Performance Share Units (PSUs) in the SKWD Form 4 for Sean W. Duffy?

PSUs are performance-based equity awards. Each PSU gives the right to receive one SKWD common share upon settlement. Duffy’s 2,861 PSUs were tied to performance from January 1, 2023 through December 31, 2025 and fully vested based on certified results.

When did Sean W. Duffy’s 2023 SKWD PSUs vest and settle?

The 2023 PSUs fully vested on December 31, 2025. They were settled in common stock after the Compensation Committee certified performance for the January 1, 2023 to December 31, 2025 period, leading to the May 6, 2026 share transactions.

What performance period applied to Sean W. Duffy’s 2023 PSUs at Skyward Specialty (SKWD)?

The PSUs were tied to a three-year performance window. Performance criteria applied from January 1, 2023 through December 31, 2025. The number of PSUs eligible to vest could range from 0% to 150% of the original 2,861-unit award.

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

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Accepted by SEC EDGAR 05/08/2026 - 04:44 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
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hours per response:			0.5

X

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^*

Duffy Sean W

(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)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	EVP & Chief Claims Officer

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	05/06/2026		M		3,805(1)	A	$0	21,768	D
Common Stock	05/06/2026		F(2)		1,671	D	$43.68	20,097	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
2023 LTIP - PSUs	(3)	05/06/2026		M			2,861	(4)	(4)	Common Stock	2,861	$0	0	D

Explanation of Responses:

1. Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Performance Share Units ("PSUs") listed in Line I of Table II.

2. The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the PSUs listed in Line I of Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

3. Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

4. On February 27, 2023, the Reporting Person was awarded 2,861 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors.

	/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.
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* Form 4: SEC 1474 (03-26)