[144] Waystar Holding Corp. SEC Filing

Rhea-AI Filing Summary

Form 144 filed for Waystar Holding Corp. (WAY) discloses a proposed sale of 50,000 common shares to be effected on 09/22/2025 through Morgan Stanley Smith Barney on NASDAQ with an aggregate market value of $1,890,000.00. The shares were acquired on 09/22/2025 by exercise of stock options and paid for in cash. The filing also reports two prior 10b5-1 sales by the same account: 46,667 shares on 07/15/2025 for $1,785,540.12 and 46,667 shares on 08/12/2025 for $1,617,577.89. The 50,000-share notice represents approximately 0.0287% of the issuer's reported 174,238,972 outstanding shares. The filer certifies there is no undisclosed material adverse information and references Rule 10b5-1 planning where applicable.

Positive

• Transaction transparency: Filing provides clear dates, broker, and dollar values for proposed and recent sales
• Compliance with 10b5-1: Prior sales are identified as 10b5-1, suggesting preplanned trades and adherence to trading rules

Negative

• Insider selling activity: Multiple sales in recent months (July, August, and proposed September 2025) show insider liquidity events
• Potential perception risk: Repeated insider sales could be viewed negatively by some investors despite small size

Insights

Securities Analyst

TL;DR: Insider option exercise followed by planned sale; size is small relative to shares outstanding, so likely limited market impact.

The filing shows an insider exercised stock options and intends to sell 50,000 common shares on 09/22/2025 through Morgan Stanley Smith Barney, valued at $1.89 million. Two prior 10b5-1 sales in July and August 2025 each moved 46,667 shares, indicating an ongoing structured selling program or recurring liquidity activity. Materiality is low: the proposed sale is roughly 0.029% of outstanding shares, which typically has limited dilution or market-moving effect. However, repeated insider sales can be of interest to investors evaluating insider liquidity versus confidence.

Corporate Governance Specialist

TL;DR: Compliance appears standard; the filer affirms no undisclosed material information and cites 10b5-1 where relevant.

The form includes required representations about lack of undisclosed material adverse information and notes use of Rule 10b5-1 plans for prior transactions. Documentation indicates the transaction arose from an option exercise and immediate registration for sale. From a governance perspective, filing on a live form and listing broker and dates meets disclosure norms. There is no indication of insider departures, extraordinary compensation, or regulatory concerns in the document.

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

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	50000	1890000.00	174238972	09/22/2025	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	09/22/2025	Exercise of Stock Options	Issuer			50000	09/22/2025	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 MATTHEW J HAWKINS 1550 Digital Drive, #300 Lehi UT 84043	Common	08/12/2025	46667	1617577.89
10b5-1 Sales for MATTHEW J HAWKINS 1550 Digital Drive, #300 Lehi UT 84043	Common	07/15/2025	46667	1785540.12

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 is the size and value of the proposed sale in the WAY Form 144?

The proposed sale is 50,000 common shares with an aggregate market value of $1,890,000.00 to be sold on 09/22/2025 on NASDAQ.

How were the 50,000 shares acquired according to the filing?

The filing states the shares were acquired on 09/22/2025 by exercise of stock options and paid for in cash.

Have any shares been sold recently by the same person for whose account these shares will be sold?

Yes; the filing reports 10b5-1 sales of 46,667 shares on 07/15/2025 for $1,785,540.12 and 46,667 shares on 08/12/2025 for $1,617,577.89.

What percentage of outstanding shares does the proposed 50,000-share sale represent?

Based on the filing's 174,238,972 shares outstanding, the 50,000-share notice represents approximately 0.0287% of outstanding shares.

Which broker is handling the proposed sale?

The broker named in the filing is Morgan Stanley Smith Barney LLC (Executive Financial Services, 1 New York Plaza, 8th Floor, New York, NY 10004).