Waystar insider plans sale of 82,500 shares

Waystar affiliate Matthew Hawkins plans a Rule 144 sale of 82,500 shares after stock option exercise, with earlier June–August 2026 10b5-1 sales also disclosed.

Rhea-AI Filing Summary

Waystar Holding Corp. (WAY) insider Matthew Hawkins has filed a notice under Rule 144 to sell up to 82,500 shares of common stock, expected on September 2, 2026, following an exercise of stock options for cash. The notice also lists multiple prior common stock sales in June–August 2026, several of which are identified as being made under a Rule 10b5-1 trading plan.

Key Figures

Planned shares to be sold: 82,500 shares Aggregate market value of planned sale: $2,125,200.00 Shares outstanding: 191,748,416 shares +5 more

8 metrics

Planned shares to be sold 82,500 shares Common stock proposed for sale by Matthew Hawkins under Rule 144

Aggregate market value of planned sale $2,125,200.00 Indicated value for 82,500 shares of common stock

Shares outstanding 191,748,416 shares Common stock outstanding referenced in the filing

Past sale on August 13, 2026 60,038 shares; $1,501,676.46 Common stock sold in a transaction labeled as a 10b5-1 sale

Past sale on August 11, 2026 22,462 shares; $562,354.14 Common stock sold in a transaction labeled as a 10b5-1 sale

Past sale on July 16, 2026 36,901 shares; $851,944.46 Common stock sold in a transaction labeled as a 10b5-1 sale

Past sale on July 15, 2026 33,099 shares; $762,031.66 Common stock sold in a transaction labeled as a 10b5-1 sale

Past sale on June 9, 2026 47,754 shares; $918,309.42 Common stock sale listed without a 10b5-1 notation

Key Terms

Rule 144, 10b5-1, Exercise of Stock Options, aggregate market value

4 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144."

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

10b5-1 regulatory

"10b5-1 Sales for MATTHEW HAWKINS 1550 Digital Drive, #300 Lehi UT 84043"

A 10b5-1 plan is a pre-set schedule that lets company insiders buy or sell shares according to written instructions made when they do not possess material, nonpublic information. Think of it as a timed automatic payment for stock trades: it helps insiders avoid accusations of trading on secret information and gives outside investors a clearer signal about whether sales are routine or potentially informative about the company’s prospects.

Exercise of Stock Options financial

"Common | 09/02/2026 | Exercise of Stock Options | Issuer"

aggregate market value financial

"Common | Morgan Stanley Smith Barney LLC Executive Financial Services ... | 2125200.00"

Aggregate market value is the combined price you would pay to buy all outstanding shares of a company or all companies in a group at current market prices — essentially the sum of each stock’s market capitalization. It matters to investors because it shows the overall size and weight of an investment or sector (like the total cost to buy every piece of a puzzle), helps compare scale across companies or markets, and influences index composition and risk exposure.

FAQ

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

What does the Form 144 filing disclose for Waystar Holding Corp. (WAY)?

It discloses that Matthew Hawkins plans to sell up to 82,500 shares of Waystar Holding Corp. common stock under Rule 144, tied to an exercise of stock options for cash, with a proposed sale date of September 2, 2026.

How many Waystar (WAY) shares are covered by the new planned sale?

The notice covers a proposed sale of 82,500 shares of common stock, to be sold through Morgan Stanley Smith Barney LLC Executive Financial Services, with an indicated aggregate market value of $2,125,200.00.

What is the acquisition method for the Waystar (WAY) shares being sold?

The 82,500 shares are indicated as acquired on September 2, 2026 through an exercise of stock options, acquired from the issuer for cash, and are the securities now proposed for sale under Rule 144.

What prior Waystar (WAY) sales by Matthew Hawkins are listed in the last 3 months?

The filing lists several past common stock sales between June 9, 2026 and August 13, 2026, including blocks such as 60,038 shares on August 13, 2026 and 47,754 shares on June 9, 2026, with dollar amounts shown for each transaction.

Were recent Waystar (WAY) sales made under a Rule 10b5-1 plan?

Yes. The filing identifies four recent transactions as “10b5-1 Sales for MATTHEW HAWKINS” on July 15, 2026, July 16, 2026, August 11, 2026, and August 13, 2026, each involving sales of Waystar common stock with disclosed share and dollar amounts.

How many Waystar (WAY) shares are outstanding compared with the planned sale?

The filing reports 191,748,416 shares of Waystar common stock outstanding. The planned Rule 144 sale of 82,500 shares is disclosed separately and uses the outstanding share figure as context only, not as the amount being sold.

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

See more from StockTitan in Google Search and AI answers. Adds StockTitan as a preferred source · opens Google

Add on Google Not now

Available on EDGAR 09/02/2026 - 04:31 PM EDT Accepted by SEC EDGAR 09/02/2026 - 04:29 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	0001998256
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	MATTHEW HAWKINS
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	Director
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	82500	2125200.00	191748416	09/02/2026	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	09/02/2026	Exercise of Stock Options	Issuer			82500	09/02/2026	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 HAWKINS 1550 Digital Drive, #300 Lehi UT 84043	Common	08/13/2026	60038	1501676.46
10b5-1 Sales for MATTHEW HAWKINS 1550 Digital Drive, #300 Lehi UT 84043	Common	08/11/2026	22462	562354.14
10b5-1 Sales for MATTHEW HAWKINS 1550 Digital Drive, #300 Lehi UT 84043	Common	07/16/2026	36901	851944.46
10b5-1 Sales for MATTHEW HAWKINS 1550 Digital Drive, #300 Lehi UT 84043	Common	07/15/2026	33099	762031.66
MATTHEW HAWKINS 1550 Digital Drive, #300 Lehi UT 84043	Common	06/09/2026	47754	918309.42

144: Remarks and Signature

Remarks
Date of Notice	09/02/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	03/13/2026
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/ Matthew Hawkins
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)