As mentioned by Cynric Endell of the Thieves Guild, Jailbreaking is when someone is hired by a client to get arrested by the guard for the purpose 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 had to sneak into jail to obtain a ring stolen by a freelance thief who was caught.
This section contains bugs related to Jail Break (Oblivion). Before adding a bug to this list, consider the following:
- To ensure an escape, even when the lockpicking skill is low, by waiting until a guard comes near the gate (make sure they can see the Hero) and lockpicking the door. Even if the lockpick breaks, the guard will see the attempt and will attack the Hero. Since they have the key they open the locked door and attempt to kill the Hero for trying to escape. Once the guard is dead, one can simply walk out the open door.
- When escaping, the Hero can have a weapon even when it's been taken. This comes in handy if the hand-to-hand skill is low. The sword Umbra can be obtained in the ruins of Vindasel (which is across the water from where the sewer exit is in the beginning of the game) from a bandit woman named Umbra. This is a quest item for Clavicus Vile. When this sword is obtained, assign it to one of the hotkeys. When escaping from prison, hit the hotkey it is assigned to and it will appear in hand, but not in the inventory. Since it is such a powerful weapon, one can easily kill all the guards with it.