Waystar Holding insider sale: 200,000 shares reported

Waystar Holding filing: reported resale and option exercises The filing on includes a reported sale by Eric L. Sinclair III of 200,000 common shares on 05/28/2026 for $3,878,900.

Rhea-AI Filing Summary

Waystar Holding filing: reported resale and option exercises

The filing on includes a reported sale by Eric L. Sinclair III of 200,000 common shares on 05/28/2026 for $3,878,900. The notice also lists two cash exercises under a registered plan on 05/29/2026 of 99,209 and 60,791 common shares, together totaling 160,000 shares with proceeds shown as $3,175,248.

Insights

Insider Transactions Specialist

TL;DR: Filing documents a reported open-market sale and related option exercises.

The excerpt shows a reported disposition by Eric L. Sinclair III of 200,000 common shares on 05/28/2026 for $3,878,900. Separate lines list two cash exercises under a registered plan on 05/29/2026 of 99,209 and 60,791 shares.

These entries are routine Section 144 disclosures documenting a sale and option exercises; cash‑flow treatment and any post‑transaction holdings are not stated in the provided excerpt. Subsequent filings or Form 4/5 may show resulting ownership changes.

Key Figures

Reported sale: 200,000 shares Proceeds from sale: $3,878,900 Option exercises (two tranches): 99,209 shares and 60,791 shares +1 more

4 metrics

Reported sale 200,000 shares sale on 05/28/2026 by Eric L. Sinclair III

Proceeds from sale $3,878,900 proceeds shown for 200,000 shares on 05/28/2026

Option exercises (two tranches) 99,209 shares and 60,791 shares cash exercises under a registered plan on 05/29/2026

Proceeds from exercises $3,175,248 proceeds shown for combined 160,000 exercised shares

Key Terms

Form 144, Exercise of options under a registered plan, Issuer

3 terms

Form 144 regulatory

"144: Securities Sold During The Past 3 Months"

Form 144 is a document that investors must file with the government when they plan to sell a large number of shares of a company's stock. It helps ensure transparency so everyone knows how many shares are being sold and when, which can impact the stock's price.

Exercise of options under a registered plan financial

"Exercise of options under a registered plan | Issuer | 99209"

Issuer regulatory

"Exercise of options under a registered plan | Issuer"

FAQ

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

What did WAY disclose in this Form 144?

The Form 144 reports a sale and option exercises. It shows 200,000 common shares sold on 05/28/2026 for $3,878,900, and two cash exercises on 05/29/2026 of 99,209 and 60,791 shares.

Who sold shares in the WAY filing?

Eric L. Sinclair III is listed as the seller for a 200,000 share transaction on 05/28/2026. The excerpt does not attribute the 05/29/2026 option exercises to a specific individual in the visible text.

How many shares were involved in the option exercises in the WAY filing?

The filing lists two cash option exercises of 99,209 and 60,791 common shares on 05/29/2026, totaling 160,000 shares with proceeds shown as $3,175,248.

Does the Form 144 state who received the cash proceeds for these transactions?

The provided excerpt shows dollar amounts for the transactions ($3,878,900 and $3,175,248) but does not state the recipient parties or detailed cash‑flow treatment in the visible lines.

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

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Accepted by SEC EDGAR 05/29/2026 - 04:16 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	0001998250
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 LEHI UTAH 84043
Phone	844-492-9782
Name of Person for Whose Account the Securities are To Be Sold	ERIC L SINCLAIR III
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

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	160000	3175248.00	191812891	05/29/2026	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	05/29/2026	Exercise of options under a registered plan	Issuer			99209	05/29/2026	Cash
Common	05/29/2026	Exercise of options under a registered plan	Issuer			60791	05/29/2026	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
ERIC L SINCLAIR III 1550 DIGITAL DRIVE LEHI UT 84043	Common	05/28/2026	200000	3878900.00

144: Remarks and Signature

Remarks
Date of Notice	05/29/2026
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/ Eric Lee Sinclair
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)