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.
The Oscar Health, Inc. (NYSE: OSCR) SEC filings page on Stock Titan brings together the company’s regulatory disclosures from the U.S. Securities and Exchange Commission, with AI-powered tools to help interpret complex documents. Oscar identifies itself in these filings as a healthcare technology company whose Class A common stock trades on the New York Stock Exchange under the symbol OSCR. Through its reports, investors can review how the company structures its health insurance operations, technology initiatives, and capital markets activities.
Oscar’s annual reports on Form 10-K and quarterly reports on Form 10-Q provide overviews of its Individual & Family health plans, health technology solutions under the +Oscar brand, risk factors, and detailed financial statements. These core filings typically include information on revenues, medical costs, selling, general, and administrative expenses, membership metrics, and key non-GAAP measures such as Adjusted EBITDA, along with management’s discussion of business drivers.
The company’s current reports on Form 8-K offer more targeted updates. Recent 8-K filings describe quarterly financial results, reaffirmed guidance, and capital structure actions such as the issuance of 2.25% Convertible Senior Subordinated Notes due 2030, related capped call transactions, and an exchange agreement involving 7.25% Convertible Senior Notes due 2031. Other 8-Ks detail amendments to investment agreements, the planned termination of a revolving credit facility in connection with a notes offering, and changes to executive employment agreements and compensation structures.
Investors can also use this page to access information on convertible debt terms, events of default, subordination provisions, and potential share dilution from note conversion, all of which are described in Oscar’s indentures and related exhibits. Stock Titan’s AI summaries help explain the implications of these filings, highlight key sections of lengthy documents, and surface important items such as changes in guidance, financing transactions, and governance-related disclosures. This makes it easier to understand how Oscar’s regulatory filings relate to its health insurance operations, technology platform, and long-term financial strategy.
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.
Oscar Health, Inc. officer reports small share sale under 10b5‑1 plan. The company’s Chief Legal Officer reported selling 1,852 shares of Class A common stock on 12/02/2025 at a weighted average price of $16.59 per share. The transaction was coded as a sale and was executed under a pre-arranged Rule 10b5-1 instruction letter entered into on August 8, 2025 to cover tax withholding obligations from vesting equity awards. After this sale, the officer beneficially owns 179,241 shares of Oscar Health, Inc. common stock directly.
Oscar Health, Inc. reported an insider stock transaction by a director and its President of Technology & CTO. On 12/02/2025, the executive sold 23,965 shares of Class A common stock in an open-market transaction coded as a sale at a weighted average price of $16.59 per share. Following this transaction, the executive directly owned 477,183 shares of Class A common stock.
The company notes that the sale was made under a Rule 10b5-1 instruction letter entered into on August 8, 2025, and was intended to satisfy the reporting person's tax withholding obligations arising from the vesting of previously granted equity awards. The reported sale occurred through multiple trades at prices ranging from $16.37 to $16.78 per share.