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Director Creager of Skyward (NASDAQ: SKWD) gains 1,797 shares as RSUs vest

Filing Impact
(Neutral)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Skyward Specialty Insurance Group director Robert E. Creager increased his direct holdings of Common Stock through the settlement of a previously granted restricted stock unit (RSU) award. On May 5, 2026, 1,797 RSUs converted into 1,797 shares of Common Stock at no cash exercise price.

The RSUs were originally granted on May 7, 2025 and were subject to Board-approved accelerated vesting to align with the end of Creager’s director term at the company’s 2026 Annual Meeting of Shareholders. Following this RSU settlement, he directly holds 54,830 shares of Common Stock.

Positive

  • None.

Negative

  • None.
Insider Creager Robert E.
Role null
Type Security Shares Price Value
Exercise 2025 RSU Award 1,797 $0.00 --
Exercise Common Stock 1,797 $0.00 --
Holdings After Transaction: 2025 RSU Award — 0 shares (Direct, null); Common Stock — 54,830 shares (Direct, null)
Footnotes (1)
  1. Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock. Each RSU represents the right to receive, at settlement, one share of Common Stock of the Issuer. On May 7, 2025, the Reporting Person was granted an RSU award of 1,797 RSUs. Subject to the terms of the award agreement, and pursuant to Board-approved accelerated vesting to coincide with the Reporting Person's director term ending at the Company's 2026 Annual Meeting of Shareholders, this award fully vested on May 5, 2026.
RSUs settled 1,797 units 2025 RSU award fully vested and settled on May 5, 2026
Shares received from RSUs 1,797 shares Each RSU settled for one share of Common Stock
Post-transaction holdings 54,830 shares Common Stock held directly after RSU settlement
Transaction price per share $0.00 Reported price for RSU settlement into Common Stock
Grant size 1,797 RSUs RSU award granted on May 7, 2025
Restricted Stock Unit financial
"Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock."
A restricted stock unit is a promise from a company to give an employee shares of stock after certain conditions are met, like staying with the company for a set amount of time. It’s like earning a bonus that turns into company stock once you’ve proven your commitment, making it a way to motivate and reward employees.
RSU financial
"On May 7, 2025, the Reporting Person was granted an RSU award of 1,797 RSUs."
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.
accelerated vesting financial
"pursuant to Board-approved accelerated vesting to coincide with the Reporting Person's director term ending"
Annual Meeting of Shareholders financial
"director term ending at the Company's 2026 Annual Meeting of Shareholders, this award fully vested"
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.
Form 4 Insider Transactions: What Each Field Means →
SEC Form 4
FORM 4UNITED 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
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*
Creager Robert E.
(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)
XDirector10% Owner
Officer (give title below)Other (specify below)
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
05/05/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm 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)
CodeVAmount(A) or (D)Price
Common Stock05/05/2026M1,797A(1)54,830D
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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
2025 RSU Award(2)05/05/2026M1,797 (3) (3)Common Stock1,797$00D
Explanation of Responses:
1. Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock.
2. Each RSU represents the right to receive, at settlement, one share of Common Stock of the Issuer.
3. On May 7, 2025, the Reporting Person was granted an RSU award of 1,797 RSUs. Subject to the terms of the award agreement, and pursuant to Board-approved accelerated vesting to coincide with the Reporting Person's director term ending at the Company's 2026 Annual Meeting of Shareholders, this award fully vested on May 5, 2026.
/s/ Stacy E. Skelton, Attorney-in-Fact05/07/2026
** Signature of Reporting PersonDate
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)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transaction did Skyward Specialty (SKWD) report for Robert E. Creager?

Skyward Specialty reported that director Robert E. Creager settled an award of 1,797 restricted stock units into an equal number of Common Stock shares. This RSU settlement increased his direct equity stake without an open-market purchase or sale.

How many Skyward Specialty (SKWD) shares does Robert E. Creager hold after this Form 4?

After the RSU settlement, Robert E. Creager directly holds 54,830 shares of Skyward Specialty Common Stock. This figure reflects his position immediately following the conversion of 1,797 restricted stock units into shares on May 5, 2026.

What was the size of the RSU award reported for Skyward Specialty (SKWD) director Creager?

The RSU award reported for director Robert E. Creager consisted of 1,797 restricted stock units. Each unit entitled him to receive one share of Skyward Specialty Common Stock upon settlement, resulting in 1,797 new shares being issued to him.

When did Robert E. Creager’s 1,797 RSUs in Skyward Specialty (SKWD) fully vest?

Robert E. Creager’s 1,797 RSUs fully vested on May 5, 2026. The vesting followed Board-approved accelerated vesting designed to coincide with the end of his director term at the company’s 2026 Annual Meeting of Shareholders.

Was there a cash exercise price for Robert E. Creager’s RSU settlement in Skyward Specialty (SKWD)?

No cash exercise price was involved in the RSU settlement; the transaction price per share was reported as $0.00. Each restricted stock unit simply settled into one share of Common Stock under the terms of the award.

What was the grant date of the 1,797 RSUs reported for Skyward Specialty (SKWD) director Creager?

The Form 4 notes that Robert E. Creager received an RSU award of 1,797 units on May 7, 2025. These units later vested in full on May 5, 2026, after Board-approved accelerated vesting tied to his director term end.