Jailbreak or jailbreaking may refer to:
- A prison escape
- '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
- Jailbreak (TV series), a reality television series presented by Craig Charles
- Jailbreak Source, a computer game modification for the Source Engine
- Computer software 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; also the description and set of technical instructions necessary to achieve a specific jailbreak or a software item designed to achieve a jailbreak.
- iOS jailbreaking, overriding the software limitations on the iPhone, iPod Touch, or iPad designed to preclude the use of applications beyond control from the device's manufacturer
- Rooting (Android OS) on Android phones and tablets,
- modifying the firmware in an (outwardly) specially designed computer device to enable its use as the general computer device it represents on the inside, such as the Sony PlayStation
- breaking out of a FreeBSD Jail
- breaking out of a UNIX/Linux chroot jail
- 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.