From "Adventures in Punishment:"
In an ideal world, you won’t have your hands cut off or spend years in a prison. But there are still many interesting ways by which a criminal past can be tied into an adventure. Being trapped in the “inescapable prison” of an evil nation can make for a very interesting adventure; having to find a way to break out without access to your usual equipment and spellbooks can be a difficult challenge. Alternately, you could play out an entire mini-campaign within a fortress prison. Perhaps you and your friends are prisoners of war; you have one week to plan and execute a massive prison break in order to support a military offensive. Can you rally the other prisoners and overcome the guards using only your wits and diplomatic skills?