Jail Break (Oblivion)

As mentioned by Cynric Endell of the Thieves Guild, Jailbreaking is when one is hired by a client to get arrested by the guard for the purpose of releasing or killing someone from within the prison. We saw an example of this in the Thieves Guild quest Ahdarji's Heirloom in Oblivion where you had to sneak into jail to obtain a ring stolen by a freelance thief who was caught.