Managed to find a workaround so I though I'd add to this for anyone encountering the same issue
I've spent a good amount of time trying to find a workaround to this and the only thing that seems to work is:
Killing the affected character
Removing all their items and picking them up
Reviving them outside of camp
Getting them arrested again
Breaking out of jail again
I'm not sure what happened but the game must've thought I was still in prison
