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Waystar Holding Corp. (WAY) insider Craig Bridge notified the SEC of a proposed sale under Rule 144 of 85,000 common shares through Morgan Stanley Smith Barney, with an aggregate market value of $3,167,950.00. The filing shows those shares were acquired on 07/19/2024 via previously exercised stock options and paid in cash on the same date. The notice lists an approximate sale date of 09/08/2025 and reports 174,238,972 shares outstanding for the issuer, with the broker exchange listed as NASDAQ. The filing also discloses prior 10b5-1 sales by Craig Bridge during the past three months: 85,000 shares on 07/21/2025 for gross proceeds of $3,152,837.00 and 15,946 shares on 06/11/2025 for $649,177.61. The filer certifies compliance with Rule 10b5-1 representations in the signature section.

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鈥�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.

Waystar Holding Corp. (WAY) insider activity by Chief Marketing Officer Melissa F. Miller. The report shows three equity transactions: 2,623 shares were withheld to pay taxes upon vesting of previously granted non-qualified stock options on 06/06/2025, reducing holdings to 193,261 shares. On 08/26/2025 a 10b5-1 plan executed the acquisition of 3,400 shares at $18.19 and simultaneous sales of 3,400 shares at a weighted-average price of $37.0095, leaving beneficial ownership at 193,261 (after a corrected prior misclassification). The Form notes the option grant dates, vesting schedule, and that the 10b5-1 plan was adopted on 11/20/2024.

Waystar Holding Corp. (WAY) amended Form 4 reporting activity by Melissa F. Miller, Chief Marketing Officer. The amendment adds an option exercise of 3,400 shares at an exercise price of $18.19 on 05/15/2025 and restates a contemporaneous sale of 3,400 shares at a weighted-average price of $39.1863. The filing shows beneficial ownership moved from 205,356 shares immediately after the exercise to 201,956 after the sale. The transactions were executed automatically under a 10b5-1 plan adopted 11/20/2024, and the amendment corrects an earlier omission of the exercise from the original Form 4.

Waystar Holding Corp. (WAY) filed a Form 144 disclosing a proposed sale of 3,400 common shares by a person who acquired the shares on 08/26/2025 through the exercise of stock options. The filing lists the broker as Morgan Stanley Smith Barney LLC and shows an aggregate market value of $122,060.00 with an approximate sale date of 08/26/2025 via the NASDAQ exchange. The filer also reported prior 10b5-1 sales by Melissa Miller totaling 6,072 shares on 06/11/2025 for gross proceeds of $247,197.19. The notice includes the standard representation that the seller is not aware of undisclosed material adverse information.

Eric L. (Ric) Sinclair III, Chief Business Officer of Waystar Holding Corp. (WAY), reported transactions dated 08/20/2025 under a Rule 10b5-1 plan adopted February 19, 2025. He exercised 9,702 stock options with a $4.14 exercise price, adding 9,702 shares and increasing beneficial ownership to 500,572 shares (includes unvested RSUs). He then sold 9,702 shares in multiple trades at a weighted average price of $35.111, reducing beneficial ownership to 490,870 shares. The exercised options are vested and total options underlying common stock held after the transaction equal 9,702 (97,012 options outstanding direct). The Form 4 was signed by an attorney-in-fact on behalf of the reporting person.

Waystar Holding Corp. insider filing: Gregory R. Packer, Chief Legal Officer, was granted 78,321 restricted stock units (RSUs) on 08/18/2025. Each RSU represents a contingent right to one share of Waystar common stock upon settlement. The RSUs vest over four years, with 40% vesting in year 3 and 60% vesting in year 4. The filing reports 131,147 shares beneficially owned following the transaction, which includes unvested RSUs. The grant was reported on Form 4 and carries a reported price of $0 (typical for RSU grants). The filing is signed by Mr. Packer on 08/19/2025.

Canada Pension Plan Investment Board disclosed ownership of 24,964,225 shares of Waystar Holding Corp. common stock, representing 14.3% of the outstanding class based on 174,238,972 shares. The shares are held directly by CPP Investment Board Private Holdings (4) Inc., a wholly owned subsidiary, and the reporting persons state shared voting power and shared dispositive power for the entire position with no sole voting or dispositive power.

This filing is a Schedule 13G/A amendment reporting an institutional investor's passive ownership stake. The statement also references an incorporated power of attorney exhibit used for signature authority.

Waystar Holding Corp. disclosure: Bain Capital-affiliated reporting persons BCPE Derby Investor, LP and BCPE Derby (DE) SPV, LP jointly report beneficial ownership. BCPE Derby holds 2,609,155 shares (~1.5%) and BCPE Derby SPV holds 15,445,894 shares (~8.9%), for a combined 18,055,049 shares representing ~10.3% of outstanding common stock based on 174,146,070 shares outstanding per the issuer's quarterly report. Neither reporting person has sole voting or dispositive power; voting and investment decisions are made by the partners of Bain Capital Investors, LLC. A Stockholders Agreement gives the reporting parties the right to nominate one director while they hold 5% or more; the Agreement requires supporting votes by other parties and the Reporting Persons expressly disclaim group membership.