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.
Gassen William reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. director William Gassen received a grant of 684 deferred stock units on July 9, 2026, as a compensation award in lieu of cash board retainer fees. Each unit represents a right to receive one share of Class A common stock and was valued at $31.20, the closing stock price on the grant date. The units are 100% vested at grant and will be settled in cash or shares, at the company’s discretion, within 45 days after specified events such as termination of service or a change in control. Following this grant, Gassen holds 7,071 deferred stock units directly.
Sankaran Sid reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. director Sid Sankaran received a grant of 858 deferred stock units on July 9, 2026, as board compensation elected in lieu of cash retainers. Each unit represents a right to receive one share of Class A common stock, valued at $31.20 per unit based on the closing share price on that date. The units are 100% vested on the grant date and will be settled in cash or shares, at the company’s discretion, within 45 days after termination of service, a change in control, death, or disability. Following this award, Sankaran directly holds 2,061 deferred stock units.
Plouffe David reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. director David Plouffe received a grant of 681 deferred stock units on July 9, 2026 as board compensation. Each unit represents a right to receive one share of Class A common stock and was valued using the Class A closing price of $31.20 on that date.
The units were issued under the Amended and Restated Deferred Compensation Plan for Directors in lieu of cash retainer payments and are 100% vested on the grant date. They will be settled in cash or Class A shares, at the company’s discretion, within 45 days after specified events such as termination of service, a change in control, death, or disability. Following this grant, Plouffe holds 7,535 deferred stock units directly.
Oscar Health, Inc. director Mario Schlosser reported trust-related transactions in the company’s common stock. A Pizzo-Schlosser Family Dynasty Trust sold a total of 47,500 shares of Class A common stock in open-market trades at weighted average prices of $29.50, $30.80, and $31.65, pursuant to a Rule 10b5-1 trading plan adopted on March 24, 2026.
On the same date, the trust converted 47,500 shares of Class B common stock into 47,500 shares of Class A common stock on a one-to-one basis. After these transactions, the trust holds 43,900 shares of Class A and 538,333 shares of Class B common stock. Schlosser also holds 480,866 Class A and 1,212,293 Class B shares directly, plus additional Class B shares through two other dynasty trusts, and he disclaims beneficial ownership of trust-held shares except to the extent of any pecuniary interest.
Oscar Health, Inc. Chief Executive Officer Mark T. Bertolini reported open-market sales of a total of 1,238,996 shares of Class A Common Stock on June 29–30, 2026. Footnotes explain these sales were made to satisfy tax withholding obligations related to deferred settlement of performance stock units that vested on April 3, 2026, under a pre-arranged Rule 10b5-1 instruction letter entered on November 10, 2025 and amended on March 24, 2026. The reported weighted average sale prices ranged from about $27.78 to $30.61 per share. Following these transactions, Bertolini directly holds 7,751,570 shares of Class A Common Stock, which the disclosure notes includes shares to be issued upon future vesting of restricted stock units.
Oscar Health, Inc. CEO Mark T. Bertolini reported open-market sales of a total of 1,206,310 shares of Class A common stock on June 25–26, 2026 at weighted average prices ranging from $28.06 to $30.17 per share. According to the filing, these transactions represent sales to satisfy tax withholding obligations related to the deferred settlement of performance stock units and time-based restricted stock units that vested on April 3, 2026, and were effected pursuant to a pre-arranged Rule 10b5-1 instruction letter. Following these transactions, Bertolini continues to hold at least 8,990,566 shares of Class A common stock directly.
Oscar Health director Mario Schlosser reported a mix of option exercises, conversions, and open-market sales of Class A common stock. Family dynasty trusts associated with him sold an aggregate of 1,027,500 shares at weighted average prices between about $28.95 and $30.09, and he has disclaimed beneficial ownership in those trust holdings except for any pecuniary interest.
On the same date, he exercised and converted derivative securities into 2,347,500 shares, including 660,000 shares from a fully vested stock option with a $9.75 exercise price. After these direct transactions, he reports holding 480,866 Class A shares and 2,092,293 Class B shares directly. The filing states that the transactions were effected under a Rule 10b5-1 trading plan adopted on March 24, 2026.
OSCR submitted a Form 144 notice for proposed sales of Common Stock through Morgan Stanley Smith Barney LLC. The filing lists 3,774,470 performance stock units and 955,555 restricted stock units vesting under a registered plan, each dated 04/03/2026.
Morgan Stanley Smith Barney LLC notice: proposed resale of Common Stock by Mario Schlosser. The filing lists 50,000 shares of Common stock associated with a 12/06/2012 acquisition and shows 34,120 shares sold in the past three months (06/02/2026). Dollar figures appear in the excerpt as $1,427,000.00 and $748,633.08.
Mario Schlosser filed a Form 144 reporting an intention to sell 50,000 shares of Common stock. The filing lists an NYSE reference with a date of 06/23/2026.
The filing also reports that 34,120 shares were sold on 06/02/2026 for $748,633.08.