Welcome to our dedicated page for Oscar Health SEC filings (Ticker: OSCR), a comprehensive resource for investors and traders seeking official regulatory documents including 10-K annual reports, 10-Q quarterly earnings, 8-K material events, and insider trading forms.
Oscar Health, Inc. filings document the public-company disclosures of a healthcare technology and health insurance issuer listed on the New York Stock Exchange under Class A common stock symbol OSCR. Its Form 8-K reports cover operating results, guidance updates, Regulation FD disclosures, material agreements and capital-structure transactions, including credit facilities, convertible notes and debt exchanges.
The company’s proxy materials disclose annual meeting matters, board governance, director elections and executive compensation. Other filings address executive employment arrangements, registered securities, risk language tied to competition, artificial intelligence and machine-learning models, internal controls and the company’s use of technology to support Individual & Family plans, +Oscar services and related healthcare marketplace offerings.
Oscar Health director William Gassen received 1,220 deferred stock units on January 8, 2026, each representing one share of Oscar Health’s Class A common stock. These units were granted under the company’s Amended and Restated Deferred Compensation Plan for Directors, as Mr. Gassen elected to take deferred stock units instead of a cash retainer for his board service.
The units were valued using the Class A common stock closing price of $16.90 on January 8, 2026, which determined how many units were issued. After this grant, Mr. Gassen beneficially owns 4,969 deferred stock units on a direct basis. The units are fully vested at grant and will be settled, in Oscar Health’s discretion, in cash or shares of Class A common stock within 45 days after the earliest of his termination of service, a change in control, death, or disability.
Oscar Health, Inc. director David Plouffe reported an award of deferred stock units as part of his board compensation. On January 8, 2026, he received 1,257 deferred stock units, each representing the right to receive one share of Oscar Health’s Class A common stock. The award was valued using the closing stock price of $16.90 per share on that date, which was used to calculate how many units he received in lieu of a cash retainer.
After this grant, Plouffe beneficially owns 5,393 deferred stock units, held directly. These units are fully vested on the grant date and will be settled, at the company’s discretion, in cash or Class A shares within 45 days after the earliest of his termination of service, a change in control, death, or disability.
Oscar Health, Inc. director and President of Technology & CTO Mario Schlosser reported a planned share sale. On January 8, 2026, he converted 23,038 shares of Class B common stock into 23,038 shares of Class A common stock at an exercise price of $0.00, then sold 23,038 Class A shares at $17.65 per share. The filing notes that the transaction was carried out under a Rule 10b5-1 trading plan adopted on September 23, 2025, which is a pre-arranged program for selling shares.
After these transactions, Schlosser directly owned 350,180 shares of Class A common stock. In addition, Class B shares held by three dynasty trusts associated with him represent 333,333, 633,333, and 333,333 shares of Class A common stock on a one-to-one conversion basis, and he disclaims beneficial ownership of those trust-held shares except to the extent of any pecuniary interest.
Oscar Health President of Technology & CTO Mario Schlosser reported converting and selling shares of the company’s stock. On January 6, 2026, he converted 76,962 shares of Class B common stock into 76,962 shares of Class A common stock and then sold 76,962 Class A shares at a weighted average price of $17.01, with individual sale prices ranging from $17.00 to $17.05. The transaction was effected under a Rule 10b5-1 trading plan adopted on September 23, 2025.
Following these transactions, Schlosser directly holds 350,180 shares of Class A common stock and 1,455,331 shares of Class B common stock. Additional Class B shares are held indirectly through three dynasty trusts in amounts of 333,333, 633,333, and 333,333 shares, each convertible into an equal number of Class A shares. Schlosser disclaims beneficial ownership of the trust-held shares except to the extent of any pecuniary interest.
A shareholder has filed a Rule 144 notice to sell up to 100,000 shares of common stock through broker Morgan Stanley Smith Barney LLC, with an aggregate market value of $1,657,000.00. The filing states that 229,010,000 shares of this class are outstanding, providing context for the size of the planned sale. The shares to be sold were acquired on 11/16/2023 by exercising stock options and were paid for in cash.
The notice also lists recent activity over the prior three months, including several Rule 10b5-1 sales. These range from 38,835 shares sold on 12/24/2025 for gross proceeds of $582,528.88 to 286,182 shares sold on 11/11/2025 for $4,369,999.14. By signing, the seller represents that they are not aware of undisclosed material adverse information about the issuer’s operations.
Oscar Health insider activity: A director and President of Technology & CTO of Oscar Health, Inc. reported pre-planned trades in Class A common stock under a Rule 10b5-1 trading plan adopted on September 23, 2025. On January 2, 2026, he converted 59,800 shares of Class B common stock into Class A stock and then sold 137,933 Class A shares at a weighted average price of $15.02. On January 5, 2026, he converted an additional 86,893 Class B shares into Class A stock and sold 96,928 Class A shares at a weighted average price of $15.64. After these transactions, he directly beneficially owned 350,180 shares of Class A common stock and continued to hold additional economic interests through convertible Class B shares and family trusts as described. The filing notes that Class B shares are convertible one-for-one into Class A and will mandatorily convert after a specified period or upon certain events.
A major shareholder has filed a notice to sell common stock under Rule 144. The filing covers a proposed sale of 216,396 common shares through Morgan Stanley Smith Barney on the NYSE, with an aggregate market value of $3,109,610.52 and 229,010,000 common shares outstanding. The shares come from restricted stock units acquired on 08/18/2021 and previously exercised options from 06/16/2019. Over the prior three months, Mario Schlosser reported several sales of common stock, including 286,182 shares on 11/11/2025 for gross proceeds of $4,369,999.14 and 105,300 shares on 11/12/2025 for $1,584,765.00, all listed as part of his trading activity.
Oscar Health, Inc. reported an insider stock sale by a person who is both a director and the company’s President of Technology & CTO. On 12/24/2025, this insider sold 38,835 shares of Class A common stock in an open-market transaction. The sale is coded as a disposition and left the insider with 438,348 shares beneficially owned directly.
The shares were sold at a weighted average price of $15.00 per share, with individual trades executed in a narrow range between $15.00 and $15.01. The filing notes that the transaction was carried out under a Rule 10b5‑1 trading plan that had been adopted on September 23, 2025, indicating it was pre-arranged rather than an ad hoc sale.
Oscar Health, Inc. disclosed that it entered into an amended and restated employment agreement with Mark T. Bertolini effective December 22, 2025. The new agreement runs through April 1, 2029, providing a multi-year commitment, and then automatically renews for additional one-year periods unless either party decides not to extend it. The company also notes that, apart from specified 2026 long-term incentive awards, Mr. Bertolini is not expected to receive additional long-term incentive or equity-based awards before calendar year 2029.
A shareholder has filed a notice under Rule 144 to sell 57,300 shares of common stock through Morgan Stanley Smith Barney LLC on or about 12/24/2025 on the NYSE, with an indicated aggregate market value of $850,332.00. The filing notes that 229,010,000 shares of this class were outstanding at the time of the notice.
The seller, identified as Mario Schlosser, acquired these 57,300 shares in an open market purchase for cash on 09/16/2021. Over the past three months, the same shareholder has reported additional sales of common shares, including 23,965 shares on 12/02/2025 for $397,579.35, 105,300 shares on 11/12/2025 for $1,584,765.00, and 286,182 shares on 11/11/2025 for $4,369,999.14.