[144] Waystar Holding Corp. SEC Filing

Rhea-AI Filing Summary

Waystar Holding Corp. (WAY) Form 144 notice reports a proposed sale of 48,507 common shares through Morgan Stanley Smith Barney LLC on 09/08/2025 with an indicated aggregate market value of $1,807,855.89. The shares were acquired on 09/08/2025 by exercise of stock options and payment was in cash. The filing lists four prior 10b5-1 sales by the same account during 06/20/2025–08/20/2025, each for 9,702 shares. The filing supplies broker, acquisition method, number of shares outstanding (174,238,972) and confirms the seller represents no undisclosed material information.

Positive

• Full disclosure of planned sale: the filing specifies broker, share count (48,507) and aggregate market value ($1,807,855.89).
• Acquisition method stated: shares were acquired by exercise of stock options and paid in cash, clarifying basis of ownership.
• Prior 10b5-1 sales disclosed: four recent sales are listed, improving transparency about ongoing insider selling.

Negative

• Insider liquidity event: proposed sale of 48,507 shares could be viewed negatively by some investors as insider selling.
• Lack of plan adoption date: the filing does not provide the date of any 10b5-1 plan adoption or instruction in the disclosed fields.

Insights

Securities Analyst

TL;DR: Insider has exercised options and plans a sizable immediate sale; disclosed recent systematic 10b5-1 sales indicate prearranged selling.

The filing documents an option exercise and a contemporaneous proposed sale of 48,507 common shares through Morgan Stanley. The presence of multiple 10b5-1 sales in June–August suggests the seller has been executing prearranged sales over recent months. This is a routine insider liquidity event disclosed under Rule 144 and Rule 10b5-1; it provides transparency about insider selling but does not, by itself, indicate operational changes at the company because no performance metrics or undisclosed information are stated in the filing.

Corporate Governance Expert

TL;DR: Disclosure follows regulatory requirements; the signer affirms no material undisclosed information and references a 10b5-1 trading plan.

The notice properly identifies the broker, the nature of acquisition (exercise of stock options), cash payment, and prior 10b5-1 sales, aligning with standard insider-reporting practices. The representation regarding absence of undisclosed material information is included as required. The filing does not provide details on plan adoption dates or signature details within the disclosed text, limiting assessment of timing relative to any blackout periods.

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	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	48507	1807855.89	174238972	09/08/2025	NASDAQ

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	09/08/2025	Exercise of Stock Options	Issuer			48507	09/08/2025	Cash

* 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
10b5-1 Sales for ERIC L SINCLAIR III 1550 Digital Drive, #300 Lehi UT 84043	Common	08/20/2025	9702	340646.92
10b5-1 Sales for ERIC L SINCLAIR III 1550 Digital Drive, #300 Lehi UT 84043	Common	07/21/2025	9702	359938.38
10b5-1 Sales for ERIC L SINCLAIR III 1550 Digital Drive, #300 Lehi UT 84043	Common	06/25/2025	9702	390256.16
10b5-1 Sales for ERIC L SINCLAIR III 1550 Digital Drive, #300 Lehi UT 84043	Common	06/20/2025	9702	366616.27

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

What shares does the WAY Form 144 propose to sell?

The filing proposes sale of 48,507 common shares through Morgan Stanley Smith Barney LLC with aggregate market value of $1,807,855.89.

How were the securities acquired for the proposed sale in the WAY filing?

The shares were acquired on 09/08/2025 by exercise of stock options and payment was made in cash.

Does the WAY Form 144 list prior insider sales?

Yes. It lists four prior 10b5-1 sales by the same account on 06/20/2025, 06/25/2025, 07/21/2025, and 08/20/2025, each for 9,702 shares.

What broker is handling the proposed sale in the WAY filing?

The proposed sale is to be handled by Morgan Stanley Smith Barney LLC located at 1 New York Plaza, 8th Floor, New York, NY 10004.

How many shares outstanding does the filing report for WAY?

The filing shows 174,238,972 shares outstanding.