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, Inc. director David Plouffe acquired 641 deferred stock units on October 8, 2026, in lieu of cash retainer payments for board service. The $33.10 per-unit figure was the Class A common stock closing price used to calculate the award, not cash paid. His reported balance after the award was 8,176 deferred stock units. Each unit represents a right to one Class A share. The units are 100% vested on the grant date and may be settled in cash or shares at the issuer’s discretion.
Oscar Health, Inc. director Sid Sankaran received an award of 1,472 deferred stock units on October 8, 2026, in lieu of cash retainer payments for board service. The reported $33.10 price was the Class A common stock closing price used to calculate the award; each unit represents a right to receive one Class A share. His reported resulting position was 3,533 deferred stock units. The units are 100% vested on the grant date and, at Oscar Health’s discretion, will be settled in cash or Class A shares within 45 days after the first of service termination, a change in control, death or disability.
Oscar Health, Inc. director William Gassen received 698 deferred stock units on October 8, 2026, in lieu of cash retainer payments for board service. The units were calculated using the Class A common stock closing price of $33.10 that day; each unit represents a right to one Class A share. The grant was 100% vested on the grant date, and Gassen held 7,769 deferred stock units directly afterward. Oscar Health may settle the units in cash or Class A shares, at its discretion, within 45 days after termination of service, a change in control, death, or disability.
Oscar Health, Inc. (OSCR) director Vanessa Ames Wittman reported selling 25,000 shares of Class A Common Stock on September 18, 2026 at $32.24 per share in a sale described as an open market or private transaction. The sale was made pursuant to a Rule 10b5-1 trading plan adopted on June 18, 2026. After this transaction, she reports 112,121 shares held directly, a figure that includes shares to be issued upon vesting of one or more restricted stock units.
Oscar Health, Inc. (OSCR) reported that on September 18, 2026, entities affiliated with director, Co-Founder and Vice Chairman, and ten percent owner Joshua Kushner reallocated Oscar’s dual-class shares among various Thrive Capital funds. Thrive Capital Partners II, III and Claremount TW exchanged specified amounts of Class B Common Stock for equal amounts of Class A Common Stock held by Thrive Capital Partners VII Growth and Claremount VII, and certain funds then made pro rata, no-consideration distributions of Class A shares to their limited partners and general partners under Rule 16a-9(a) and Rule 16a-13. Class B Common Stock is convertible into Class A Common Stock on a one-to-one basis and will mandatorily convert after a set period and upon certain events, and Kushner, as sole managing member of the Thrive general partners, disclaims beneficial ownership except to the extent of his pecuniary interest.
Oscar Health, Inc. (OSCR) reported that multiple Thrive Capital funds restructured their holdings on September 18, 2026 using "J" code transactions, exchanging large blocks of Class A and Class B Common Stock among affiliated funds at a stated price of $0.00 per share. The moves included exchanges between Thrive Capital Partners II, III and Claremount TW and Thrive Capital Partners VII Growth and Claremount VII, plus pro rata distributions of Class A shares to limited partners and general partners without consideration, relying on Exchange Act Rules 16a-9(a) and 16a-13. All positions are held indirectly through the Thrive Capital funds, and Joshua Kushner, as managing member of the general partners, has voting and investment power but disclaims beneficial ownership except for his pecuniary interests.
Oscar Health, Inc. (OSCR) is the subject of an Amendment No. 4 to a Schedule 13D filed by investment entities affiliated with Thrive Capital and Joshua Kushner, updating their beneficial ownership of the company’s Class A Common Stock. Based on 273,469,000 Class A shares outstanding as of July 31, 2026, Joshua Kushner is reported as beneficially owning 37,525,451 shares, or 12.1% of the Class A Common Stock (treating Class B and certain convertible securities as converted solely for this calculation.
The amendment details Oscar’s dual-class structure, where Class A shares carry one vote and Class B shares carry 20 votes and are convertible into Class A, with automatic conversion after a set period or upon specified events. On September 18, 2026, various Thrive Capital funds executed exchanges of Class B for Class A shares among themselves and then made pro rata, no‑consideration distributions of Class A shares to their limited partners and general partners, with follow‑on pro rata distributions by the general partner entities. Certain Thrive funds also hold Oscar Convertible Notes, which may be converted into additional Class A shares at a stated Conversion Rate.
Oscar Health, Inc. (OSCR) is the issuer for a planned sale of its Class A Common Stock by officer Vanessa Wittman under a Rule 144 notice. The notice covers up to 25,000 shares, with an aggregate market value of $806,000, to be sold through Merrill Lynch on the NYSE on or about September 18, 2026.
The filing reports that 273,469 shares of this class were outstanding in the relevant Form 144 table. The shares to be sold stem from vesting of restricted stock unit awards granted as part of Oscar Health’s equity compensation plan, including tranches of 8,333 shares on September 1, 2021 and 4,167 or 4,166 shares vesting on multiple dates in 2021–2022.
Oscar Health, Inc. (OSCR) announced updated full year 2026 guidance in connection with its Investor Day, including higher expected profitability and slightly improved medical cost ratios. The company now expects Earnings from Operations between $600 million and $800 million, up by $100 million from the prior range of $500 million to $700 million.
Oscar also tightened its expected Medical Loss Ratio to 81.0%–82.0%, improving this range by 50 basis points from its previous 81.5%–82.5% outlook. The company reaffirmed its 2026 guidance for Total Revenue of $18.7 billion to $19.0 billion and an SG&A Expense Ratio of 15.6%–16.1%. Management plans to discuss strategy, long-term financial targets, and this updated outlook at its September 16, 2026 Investor Day, with materials and a webcast available on its investor relations website.
Oscar Health, Inc. (OSCR) reported that Janet Liang, President, Oscar Insurance, sold 10,360 shares of Class A Common Stock on September 3, 2026 at a weighted average price of $31.45 per share. The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy tax withholding obligations upon vesting of equity awards. Following this transaction, she holds 248,697 shares directly, including shares to be issued upon vesting of restricted stock units.