As mentioned by Cynric Endell of the Thieves Guild, Jailbreaking is the event when an individual is hired by a client, typically to be arrested by the guard. The purpose of such an act is for the sake of releasing or killing someone from within the prison. An example of this can be seen in the Thieves Guild quest, Ahdarji's Heirloom in The Elder Scrolls IV: Oblivion, where the Hero must sneak into jail in order to obtain a ring stolen by a freelance thief who had been previously caught.