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Jailbreak or jailbreaking refers to a prison escape. It may also refer to:
- '74 Jailbreak, an album by the rock band AC/DC
- Jailbreak (AC/DC song), a song by the rock band AC/DC
- Jailbreak (album), a 1976 album by the rock band Thin Lizzy
- Jailbreak (Thin Lizzy song), the title track of the Thin Lizzy album
 Film and television
- Jailbreak (TV series), a UK reality television series presented by Craig Charles
- Jailbreakers, a 1994 television film
- Prison Break, an American TV series
- Privilege escalation, a jargon expression for (the act of) overcoming limitations in a computer system or device that were deliberately placed there for security, administrative, or marketing reasons:
- Jailbreak: Source, a multiplayer computer game modification of the Source game engine
- A variant of Tag (game)
- An activity, often sponsored for charity at many UK universities, in which participants aim to get as far away from the university as possible in a specified time without spending any money or using their own means of transportation.
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