We have broken down every major breakout attempt across Fox River, Sona, Ogygia, and Miami-Dade. Verified by on-screen events (and ignoring post-credits teases unless confirmed in later seasons), here is the definitive answer.
Across the series, the following groups and individuals successfully made it past the prison walls: Known as the who escapes in prison break verified
This is the primary escape from Fox River State Penitentiary. Eight men successfully made it out of the prison walls in the first season finale. We have broken down every major breakout attempt