Set in a grim totalitarian futuristic society,a rather physically well-endowed red-headed female thief named Shlla is captured by the guards and put in prison.

The gameplay mostly consists of exploring the prison and its surroundings, picking up clues, talking to characters to gain information, etc. There are no real puzzles in the game; most of the time it is just necessary to initiate certain conversations to trigger events or pick up specific items for later usage. There are also some action-based segments in the game, including a few combat sequences, situations which require quick movement, and timed events.

Jailbreaker is set in a grim totalitarian futuristic society, and stars a rather physically well-endowed red-headed female thief named Shlla (sic, according to the game's manual and cover art), who is sought by the authorities and is the only "dangerous criminal" who hasn't been caught yet. One night she attempts a robbery and fails; shortly thereafter, she is captured by the guards and put in prison. Once there, communication with inmates convinces her that something worse than just prison awaits them all... and she is the only one who can find a way to escape.