Waystar (WAY) Form 144: Insider Plans $1.06M Sale of 25,869 Shares

Waystar Holding Corp. (WAY) insider sale notice: This Form 144 reports a proposed sale of 25,869 common shares through Morgan Stanley Smith Barney on 09/10/2025, with an aggregate market value of $1,057,783.41 and listing on NASDAQ.

Rhea-AI Filing Summary

Waystar Holding Corp. (WAY) insider sale notice: This Form 144 reports a proposed sale of 25,869 common shares through Morgan Stanley Smith Barney on 09/10/2025, with an aggregate market value of $1,057,783.41 and listing on NASDAQ. The shares were acquired the same day via exercise of stock options and payment was in cash. The filer also recorded two prior 10b5-1 sales this year: 8,623 shares on 08/11/2025 for $297,391.75 and 8,623 shares on 07/10/2025 for $324,461.93. The notice includes the standard representation that the seller is not aware of undisclosed material adverse information.

Positive

• Full disclosure of transaction details including dates, share counts, broker, and gross value
• Use of a broker and documented 10b5-1 sales indicates adherence to established trading procedures

Negative

• Insider proposes sale of 25,869 shares valued at $1,057,783.41, which may be viewed negatively by some investors

Insights

Securities Compliance Analyst

TL;DR: Routine Form 144 filing for exercised options being sold; includes prior 10b5-1 trades, consistent with planned insider dispositions.

The filing documents a proposed sale of 25,869 shares acquired by option exercise on the same date of intended sale, using Morgan Stanley Smith Barney as broker and executed on NASDAQ. The inclusion of two recent 10b5-1 sales with dates, share counts, and gross proceeds suggests the seller has used or is using pre-established trading arrangements. From a compliance perspective this is a standard disclosure to satisfy Rule 144 requirements and to notify the market of an insider sale equal to roughly $1.06 million in market value.

Equity Research Analyst

TL;DR: Insider liquidity event of modest scale for a publicly traded company; not an earnings or operational signal.

Quantitatively, the proposed sale of 25,869 shares at an aggregate market value of $1,057,783.41 is explicit and identical-date acquisition and disposition via option exercise indicates immediate monetization of vested compensation. Prior 10b5-1 sales of 8,623 shares on two earlier dates with reported gross proceeds are provided, allowing investors to track recent insider selling activity. This filing itself conveys transactional facts without commentary on company fundamentals.

FAQ

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

What does Waystar Holding Corp.'s Form 144 filed for symbol WAY report?

It reports a proposed sale of 25,869 common shares to be executed on 09/10/2025 through Morgan Stanley Smith Barney with aggregate market value $1,057,783.41.

How were the 25,869 Waystar shares acquired according to the filing?

The filing states the shares were acquired on 09/10/2025 by exercise of stock options and payment was made in cash.

Were there any recent insider sales by the same person in the past three months?

Yes. The filer reported two 10b5-1 sales: 8,623 shares on 08/11/2025 for $297,391.75 and 8,623 shares on 07/10/2025 for $324,461.93.

Which broker and exchange are named in the Form 144?

The broker is Morgan Stanley Smith Barney LLC and the securities exchange listed is NASDAQ.

Does the Form 144 indicate any undisclosed material information about Waystar?

No. The filer signed the standard representation that they do not know any material adverse information about the issuer that has not been publicly disclosed.

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

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Accepted by SEC EDGAR 09/10/2025 - 04:38 PM EDT Learn about SEC filing dates

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	0001998333
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	WAYSTAR HOLDING CORP
SEC File Number	001-42125
Address of Issuer	1550 Digital Drive, #300 Lehi UTAH 84043
Phone	8444929782
Name of Person for Whose Account the Securities are To Be Sold	CHRISTOPHER SCHREMSER
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	Officer

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	25869	1057783.41	174238972	09/10/2025	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	09/10/2025	Exercise of Stock Options	Issuer			25869	09/10/2025	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 CHRISTOPHER SCHREMSER 1550 Digital Drive, #300 Lehi UT 84043	Common	08/11/2025	8623	297391.75
10b5-1 Sales for CHRISTOPHER SCHREMSER 1550 Digital Drive, #300 Lehi UT 84043	Common	07/10/2025	8623	324461.93

144: Remarks and Signature

Remarks	The securities to be sold were and will be received upon the exercise of stock options over the next three months. The dates of acquisition and payment were and will be the dates of exercise/sale.
Date of Notice	09/10/2025
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	12/06/2024
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	/s/ Christopher Schremser
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)