Skyward Specialty grants 108,154 RSUs to executive

Slaughter James Richard reported acquisition or exercise transactions in this Form 4 filing.

Rhea-AI Filing Summary

Slaughter James Richard reported acquisition or exercise transactions in this Form 4 filing.

Skyward Specialty Insurance Group, Inc. reported that executive James Richard Slaughter, CUO - Apollo, received a grant of 108,154 Restricted Stock Units (RSUs) on February 25, 2026. Each RSU represents the right to receive one share of common stock upon settlement.

According to the award terms, 50% of these RSUs are scheduled to vest on January 1, 2029 and the remaining 50% on January 1, 2030, contingent on his continuous service. Following this filing, he reports direct ownership of 55,475 shares of common stock and indirect ownership of 12,724 shares through the Hillside Family Trust 2025, where he serves as trustee.

Insider Trade Summary

Grant/Award: 108,154 shares

Grant/Award 3 txns

Insider Slaughter James Richard

Role CUO - Apollo

Type	Security	Shares	Price	Value
Grant/Award	2026 MIP - RSUs	108,154	$0.00	$0.00
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: 2026 MIP - RSUs — 108,154 contracts (Direct); Common Stock — 55,475 shares (Direct); Common Stock — 12,724 shares (Indirect, Hillside Family Trust 2025)

Footnotes (3)

1. F1. The Reporting Person is Trustee of the entity.
2. F2. Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement.
3. F3. On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 108,154 RSUs. Subject to the terms of the RSU Agreement and the Reporting Person's continuous service through the vesting dates, 50% of the RSUs shall vest on January 1, 2029 and the remaining 50% of the RSUs will vest on January 1, 2030.

FAQ

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

What did the Skyward Specialty (SKWD) Form 4 report for James Richard Slaughter?

The Form 4 shows James Richard Slaughter received a grant of 108,154 RSUs. These units are part of the 2026 MIP and represent potential future shares of Skyward Specialty common stock, subject to vesting conditions and his continued service.

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

James Richard Slaughter was granted 108,154 Restricted Stock Units. Each RSU corresponds to one share of Skyward Specialty common stock upon settlement, giving him a significant potential future equity interest if vesting and service conditions are satisfied.

What is the vesting schedule for the 108,154 RSUs at Skyward Specialty (SKWD)?

The 108,154 RSUs vest in two equal installments. Half of the RSUs vest on January 1, 2029, and the remaining half vest on January 1, 2030, assuming James Richard Slaughter remains in continuous service through each vesting date.

What does each RSU represent in the Skyward Specialty (SKWD) award?

Each Restricted Stock Unit represents the right to receive one share of Skyward Specialty common stock. The actual shares are delivered upon settlement after vesting, aligning the executive’s potential value with the company’s future stock performance.

What direct and indirect share holdings does James Richard Slaughter report in SKWD?

After the reported transactions, he directly holds 55,475 shares of Skyward Specialty common stock. He also indirectly holds 12,724 shares through the Hillside Family Trust 2025, where he is the trustee according to the filing footnotes.

What role does the Hillside Family Trust 2025 play in Skyward Specialty (SKWD) ownership?

The Hillside Family Trust 2025 holds 12,724 Skyward Specialty common shares indirectly attributed to James Richard Slaughter. The filing notes he serves as trustee of this entity, which explains why these shares are reported as indirect beneficial ownership.

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

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Accepted by SEC EDGAR 02/27/2026 - 04:05 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^*

Slaughter James Richard

(Last) (First) (Middle)

800 GESSNER

SUITE 600

(Street)

HOUSTON TX 77024

(City) (State) (Zip)

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)	X	Other (specify below)
	CUO - Apollo		Division of Skyward Group

3. Date of Earliest Transaction (Month/Day/Year)
02/25/2026

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

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

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

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								55,475	D
Common Stock								12,724	I	Hillside Family Trust 2025(1)

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 MIP - RSUs	(2)	02/25/2026		A		108,154		(3)	(3)	Common Stock	108,154	$0	108,154	D

Explanation of Responses:

1. The Reporting Person is Trustee of the entity.

2. Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement.

3. On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 108,154 RSUs. Subject to the terms of the RSU Agreement and the Reporting Person's continuous service through the vesting dates, 50% of the RSUs shall vest on January 1, 2029 and the remaining 50% of the RSUs will vest on January 1, 2030.

	/s/ Stacy E. Skelton, Attorney-in-Fact	02/27/2026
	** 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.