| Sep 18, 2026 | AMES VANESSA WITTMAN | DIRECTOR | SELL | 25.000K | $32.24 | $806K |
| Sep 3, 2026 | Janet Liang | PRESIDENT, OSCAR INSURANCE | SELL | 10.360K | $31.45 | $326K |
| Sep 3, 2026 | Victoria Baltrus | CHIEF ACCOUNTING OFFICER | SELL | 958.000 | $31.45 | $30K |
| Sep 3, 2026 | Scott Richard Blackley | CHIEF FINANCIAL OFFICER | SELL | 28.869K | $31.45 | $908K |
| Sep 3, 2026 | Adam McAnaney | CHIEF LEGAL OFFICER | SELL | 9.092K | $31.45 | $286K |
| Sep 3, 2026 | Mario Schlosser | DIRECTOR | SELL | 31.422K | $31.45 | $988K |
| Aug 27, 2026 | Mario Schlosser | DIRECTOR | SELL-OPTIONS | — | $30.43 | $22.8M |
| Aug 18, 2026 | Scott Richard Blackley | CHIEF FINANCIAL OFFICER | SELL | 18.750K | $31.74 | $595K |
| Jul 1, 2026 | Mario Schlosser | DIRECTOR | SELL-OPTIONS | — | $31.24 | $1.5M |
| Jun 29, 2026 | Mark Bertolini | CHIEF EXECUTIVE OFFICER | SELL | 1.239M | $28.87 | $35.8M |
| Jun 25, 2026 | Mark Bertolini | CHIEF EXECUTIVE OFFICER | SELL | 1.206M | $28.94 | $34.9M |
| Jun 23, 2026 | Mario Schlosser | DIRECTOR | SELL-OPTIONS | — | $29.38 | $30.2M |
| Jun 2, 2026 | Victoria Baltrus | CHIEF ACCOUNTING OFFICER | SELL | 1.523K | $21.94 | $33K |
| Jun 2, 2026 | Mario Schlosser | DIRECTOR | SELL | 34.120K | $21.94 | $749K |
| Jun 2, 2026 | Adam McAnaney | CHIEF LEGAL OFFICER | SELL | 9.859K | $21.94 | $216K |
| Jun 2, 2026 | Janet Liang | PRESIDENT, OSCAR INSURANCE | SELL | 12.475K | $21.94 | $274K |
| Jun 2, 2026 | Scott Richard Blackley | CHIEF FINANCIAL OFFICER | SELL | 31.683K | $21.94 | $695K |
| May 18, 2026 | Scott Richard Blackley | CHIEF FINANCIAL OFFICER | SELL | 110.000K | $25.03 | $2.8M |
| May 14, 2026 | Scott Richard Blackley | CHIEF FINANCIAL OFFICER | SELL | 100.000K | $23.16 | $2.3M |
| Apr 3, 2026 | Mark Bertolini | CHIEF EXECUTIVE OFFICER | BUY | 5.733M | $11.92 | $12 |
