For other uses, see Jail Break.

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.


This section contains bugs related to Jail Break (Oblivion). Before adding a bug to this list, consider the following:

  1. Please reload an old save to confirm if the bug is still happening.
  2. If the bug is still occurring, please post the bug report with the appropriate system template  360  / XB1  ,  PS3  / PS4  ,  PC  / MAC  ,  NX  , depending on which platform(s) the bug has been encountered on.
  3. Be descriptive when listing the bug and fixes, but avoid having conversations in the description and/or using first-person anecdotes: such discussions belong on the appropriate forum board.
  • To ensure an escape, despite the event in which the Lockpicking skill is low, one is meant to wait until a guard begin to approach the gate, ensuring that the Hero is seen — and Lockpicking the door. Even if the lockpick breaks, the guard will bear witness to the attempt, causing them to attack the Hero. Since the key is in possession of the guard, they can open the locked door. Therefore, an effort to kill the Hero for trying to escape will ensue. However, once the guard is dead, one can simply walk out the open door.
  • When escaping, the Hero can keep a weapon — even when said weapon has been stolen. The situation comes in handy in the event that the hand-to-hand skill is sub par. 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. The sword is a quest item for Clavicus Vile. When this sword is obtained, assign it to any of the hotkeys. When escaping from prison, hit the hotkey it is assigned to, and it will appear in hand. However, the sword will not show up in the inventory. Even so, since it is such a powerful weapon, one can easily kill all the guards with it.