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 Mario Schlosser reported selling a total of 34,120 shares of Class A common stock on June 2, 2026 in two open-market transactions. He sold 9,668 shares at a weighted average price of $22.45 and 24,452 shares at a weighted average price of $21.74.
According to the footnotes, these sales were effected under a Rule 10b5-1 instruction letter entered into on August 8, 2025, to satisfy his tax withholding obligations arising from the vesting of previously granted equity awards. The prices reflect multiple trades within stated ranges on that date.
Oscar Health, Inc. Chief Legal Officer Adam McAnaney reported selling a total of 9,859 shares of Class A common stock in two open-market transactions. One sale covered 2,794 shares at a weighted average price of about $22.45 per share, and the other covered 7,065 shares at about $21.74 per share. According to the disclosure, these sales were carried out under a pre-arranged Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy tax withholding obligations upon the vesting of previously granted equity awards. The prices reflected multiple trades within ranges of $21.03 to $22.02 and $22.03 to $22.96 per share.
Oscar Health, Inc. President, Oscar Insurance, Janet Liang reported open-market sales of a total of 12,475 shares of Class A common stock on June 2, 2026. The transactions were executed at weighted average prices of about $21.74 and $22.45 per share.
According to the disclosure, these sales were effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy her tax withholding obligations arising from the vesting of previously granted equity awards. The filing notes that her holdings include shares to be issued upon vesting of restricted stock units.
Oscar Health, Inc. Chief Financial Officer Richard Scott Blackley reported open‑market sales of 31,683 shares of Class A Common Stock on June 2, 2026. The shares were sold in two transactions of 8,977 shares at $22.45 and 22,706 shares at $21.74 per share. A footnote states the sales were effected under a Rule 10b5‑1 instruction letter entered into on August 8, 2025 to satisfy the reporting person’s tax withholding obligations upon vesting of previously granted equity awards. The filing also notes 75,000 shares held indirectly by the MQB Irrevocable Trust.
OSCR submitted a Form 144 reporting the proposed sale of 66,085 shares tied to restricted stock units vesting under a registered plan on 06/01/2026.
The filing also discloses prior sales by Richard Scott Blackley: 19,221 shares on 03/02/2026 ($257,369.19), 91,259 shares on 05/14/2026 ($2,108,082.90), 8,741 shares on 05/14/2026 ($207,948.39), and 110,000 shares on 05/18/2026 ($2,753,300.00).
OSCR registers 18,447 shares of Common Stock to be sold arising from restricted stock units vesting under a registered plan on 06/01/2026. The filing also reports an insider sale: Adam McAnaney sold 18,710 shares on 03/02/2026 for $250,526.90.
The scheduled sale is tied to RSU vesting under a registered plan and is described as "Services Rendered." The filing lists broker/dealer details and an NYSE listing. Timing and cash‑flow treatment for the planned sale follow the vesting event noted.
OSCR filed a Form 144 reporting a proposed sale of 23,038 shares of Common Stock on 06/01/2026 arising from restricted stock units vesting under a registered plan. The filing also lists a prior sale of 7,453 shares on 03/02/2026 for $99,795.67.
OSCR insider reports a sale under Rule 144. Mario Schlosser reported disposition of 24,335 shares of Common Stock on 03/02/2026 for $325,845.65. The filing also lists 58,940 restricted stock units vesting under a registered plan on 06/01/2026.
Oscar Health, Inc. has amended and restated the employment agreement for co-founder Mario Schlosser, effective June 1, 2026, as he transitions from President of Technology and Chief Technology Officer to Co-Founder & Advisor to the CEO. In his new role, he will focus on accelerating the company’s artificial intelligence and digital health initiatives and will remain on the Board of Directors.
Under the new agreement, Mr. Schlosser’s annual base salary will be $370,000. Beginning with calendar year 2026, he will no longer be eligible for an annual bonus or for new long-term incentive or equity-based awards, although his existing equity awards will continue to vest under their current terms. He will also not be entitled to cash severance payments or company-subsidized healthcare coverage upon any termination of employment.
Oscar Health Chief Financial Officer Richard Scott Blackley sold 110,000 shares of Class A Common Stock in an open-market transaction at a weighted average price of $25.03 per share. The sale was carried out pursuant to a Rule 10b5-1 trading plan adopted on February 12, 2026, indicating it was pre-arranged. After the sale, he holds 1,106,660 shares directly, and an additional 75,000 shares are held indirectly by the MQB Irrevocable Trust, which includes shares to be issued upon vesting of restricted stock units.