Insider plans 2,616-share Skyward Specialty (NYSE: SKWD) sale

Rhea-AI Filing Summary

A shareholder of Skyward Specialty Insurance Inc. has filed a notice of proposed sale under Rule 144 for 2,616 shares of common stock. The planned sale, through Merrill Lynch, has an aggregate market value of $113,695.75 and is targeted around February 9, 2026 on the NYSE.

The filing notes that 40,487,365 shares of common stock were outstanding, providing context for the size of the planned transaction. The shares to be sold were acquired as stock bonus compensatory payments on January 1, 2025. In the past three months, a prior sale of 88 shares generated $4,169.73 in gross proceeds.

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK
Filer CCC
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.

Relationship to Issuer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common Stock	Merrill Lynch 800 Capitol St. Houston TX 77002	2616	113695.75	40487365	02/09/2026	NYSE

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common Stock	01/01/2025	Stock bonus	Skyward Specialty Insurance Inc			637	01/01/2025	Compensatory payment
Common Stock	01/01/2025	Stock bonus	Skyward Specialty Insurance Inc			284	01/01/2025	Compensatory payment
Common Stock	01/01/2025	Stock bonus	Skyward Specialty Insurance Inc			229	01/01/2025	Compensatory payment
Common Stock	01/01/2025	Stock bonus	Skyward Specialty Insurance Inc			33	01/01/2025	Compensatory payment
Common Stock	01/01/2025	Stock bonus	Skyward Specialty Insurance Inc			657	01/01/2025	Compensatory payment
Common Stock	01/01/2025	Stock bonus	Skyward Specialty Insurance Inc			776	01/01/2025	Compensatory payment

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
Merrill Lynch 800 Capitol St. Houston TX 77002	Common Stock	12/11/2025	88	4169.73

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

ATTENTION:

The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.

Signature

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

How many Skyward Specialty (SKWD) shares are planned for sale under this Form 144?

The notice covers a proposed sale of 2,616 shares of Skyward Specialty Insurance Inc. common stock. These shares have an aggregate market value of $113,695.75 based on the figures in the filing and are expected to be sold on the NYSE.

When is the planned Rule 144 sale for Skyward Specialty (SKWD) expected to occur?

The planned Rule 144 sale is targeted for an approximate date of February 9, 2026. The transaction is listed to occur on the NYSE through Merrill Lynch, subject to normal market conditions and Rule 144 requirements as indicated in the notice.

What is the market value of the Skyward Specialty (SKWD) shares in this Form 144?

The filing shows an aggregate market value of $113,695.75 for the 2,616 common shares covered by the notice. This value reflects the estimated worth of the proposed sale at the time of filing, tied to trading on the NYSE.

How were the Skyward Specialty (SKWD) shares being sold under Rule 144 acquired?

The shares were acquired as stock bonus compensatory payments from Skyward Specialty Insurance Inc. on January 1, 2025. Multiple entries list stock bonus awards with the same acquisition and payment date, indicating compensation-related equity grants rather than open-market purchases.

How many Skyward Specialty (SKWD) shares were sold in the last three months before this notice?

The filing reports a prior sale of 88 shares of common stock on December 11, 2025, producing $4,169.73 in gross proceeds. This disclosure covers sales in the preceding three months that must be aggregated under Rule 144 requirements.

How large is the planned Skyward Specialty (SKWD) sale relative to shares outstanding?

The notice states that 40,487,365 shares of common stock were outstanding. The proposed sale involves 2,616 shares, a small fraction of this baseline share count, helping investors gauge the relative size of the Rule 144 transaction.