Oscar Health Inc SEC Filings

Oscar Health (OSCR) reported a director equity transaction. A director received 1,034 deferred stock units on October 9, 2025 at $20.54 per unit under the company’s Amended and Restated Deferred Compensation Plan for Directors, electing DSUs in lieu of a cash retainer. Each DSU represents the right to receive one share of Class A common stock and is 100% vested on the grant date. DSUs will be settled for cash or shares, at the company’s discretion, within 45 days of the earliest of termination of service, a change in control, death, or disability. Following this grant, the reporting person held 4,136 derivative securities directly.

Oscar Health (OSCR) Form 4: A director acquired 2,555 deferred stock units on October 9, 2025, reported with transaction code A. The price of $20.54 reflects the Class A common stock closing price used to calculate the number of units under the company’s director deferred compensation plan. Each unit represents a right to receive one share of Class A common stock. Following this grant, the director beneficially owned 63,142 derivative securities, held directly. The units are 100% vested on the grant date and will be settled in cash or shares at the company’s discretion upon specified triggering events.

Oscar Health insider filings show option exercise and share sale by Mario Schlosser. Mr. Schlosser exercised 555,165 vested stock options with a $6.36 exercise price on 09/22/2025, creating the right to 555,165 Class A shares. Concurrently he converted and sold 395,000 Class A shares in multiple transactions at a weighted average price of $18.43 to cover the exercise cost and tax withholding, leaving him with 501,148 Class A shares beneficially owned. Certain remaining shares are held indirectly in family dynasty trusts over which he disclaims beneficial ownership except for any pecuniary interest.

Oscar Health, Inc. (OSCR) submitted a Form 144 notice reporting a proposed sale of 395,000 common shares through Morgan Stanley Smith Barney LLC on the NYSE with an approximate aggregate market value of $7,280,995.50. The filing shows the shares were acquired and will be sold on 09/22/2025 via exercise of options under a registered plan and payment was in cash. The filer reports 223,044,000 shares outstanding for the issuer and indicates no other securities were sold in the past three months. The notice includes the standard representation that the seller is unaware of undisclosed material adverse information.

Oscar Health, Inc. filed an 8-K reporting execution of an Indenture dated September 18, 2025 between the company and U.S. Bank Trust Company, National Association as trustee. The filing includes the form of certificate for 2.25% Convertible Senior Subordinated Notes due 2030 (Exhibit A to Exhibit 4.1) and a form of Capped Call Confirmation. The submission also contains the cover page interactive data file embedded in the inline XBRL document. The filing is signed by R. Scott Blackley, Chief Financial Officer.

Oscar Health, Inc. filed an 8-K reporting that it has given notice of its intent to terminate the revolving credit facility that is part of its senior secured credit agreement with Wells Fargo Bank, N.A. and other lenders; the termination is contingent on the closing of an offering and will occur concurrently with that closing. The company disclosed an offering of notes to qualified institutional buyers under Rule 144A, and attached a press release as Exhibit 99.1. The report is signed by R. Scott Blackley, Chief Financial Officer and dated September 16, 2025.

Oscar Health, Inc. disclosed an amendment to its January 27, 2022 Investment Agreement with Dragoneer-affiliated funds to permit an offering of securities. The filing states the company expects to terminate its revolving credit facility concurrently with the closing of the offering; that termination is contingent on the offering closing. The offering is described as a Rule 144A placement to qualified institutional buyers. A press release dated September 15, 2025 is attached as Exhibit 99.1 and the report is signed by Chief Financial Officer R. Scott Blackley.

Victoria Baltrus, identified as the issuer's Chief Accounting Officer, reported a transaction on 09/02/2025 involving Class A common stock of Oscar Health, Inc. (OSCR). The filing shows a Code F disposition on 09/02/2025 where 6,266 shares were withheld by the issuer to satisfy tax withholding at a reported price of $16.66 per share. After the transaction, Baltrus is reported to beneficially own 207,599 shares, which the filing states includes shares to be issued upon RSU vesting. The form was signed by an attorney-in-fact on 09/04/2025.

Oscar Health insider reported a disposition of Class A common stock by Richard Scott Blackley, the company's Chief Financial Officer and director. On 09/02/2025 the filing shows 28,166 shares of Class A common stock were disposed of under transaction code F at a price of $16.66 per share. After the reported transaction, Mr. Blackley beneficially owned 1,376,169 shares. The filing explains 28,166 shares were withheld by the issuer to satisfy tax withholding on vested restricted stock units and that the post-transaction holdings include shares to be issued upon RSU vesting. The Form 4 was signed by an attorney-in-fact on 09/04/2025.