And your friends could bail you out.
It would give you free passage in the town for a whole of 24 hours real time.
I wouldn't go that far but a really hard speech check and a hefty bribe might get you 'informally released' to the world map. With added timer gain/rep loss for your 'escape'.
You realize you'd have to sit in a jail for about two real life weeks?
Only if you were -2000 to start with, and if you were then why were you there?, a real 'wastelands is harsh' response for that situation would be a lynching (perma-death). Compared to that 2 weeks, that you knew ahead of time were the consequence of failure, seems reasonable. But if that's too harsh then the 'prison jobs' could add something like +1 rep per shit shoveled instead of paying caps.