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Jailbreak is a main quest in Fallout: New California
Detailed walkthrough
The quest is started if you were detained during the quest Bridge Over Eye-15 either by being rude to General Silverman or by wearing a Vault 18 jumpsuit when entering Union City.
Once you have been arrested, you will be teleported to the Union City jail in a cell with an old man throwing up and a prostitute. You must escape the jail within 12 in-game hours or a Raider Vertibird will drop a bomb on Union City, killing the player and failing the quest. There are several ways out of the cell:
Lockpick & Sneak
You can pick the lock to your cell and sneak out. You must wait until nightfall when the guards are less active. You will need relatively high sneak and lockpick skills to do this.
Bribe Guard
It is possible to bribe the guards in the jail into letting you go. In order to do this, you need a very high charisma and some luck.
Blow the Wall
The final option is blowing the wall to the jail to escape. To do this you need to work with the prostitute as she has a stick of dynamite with her. You will need to get a lighter in order to blow the wall; the lighter is located in the cell next to you with the drunken man. In order to reach the lighter, use the mod or broom located next to you to pull the lighter towards you. Once you have the lighter, you can either give it to the prostitute and she will light it or you can convince her to give you the dynamite and you can light it yourself.
Once you have escaped, all NCR will be hostile towards you and you can no longer pursue the NCR quest line. This is however the bridge to the Survivalist Raider quest line. You can start it by following the marker to Athens-Tec given to you as a part of the Lost Roads quest. If you escaped with the prostitute, she will follow you there.
You will be captured as normal and wake up in Athens-Tec to start HELL’S GATE. The prostitute will disappear once you are captured.