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Or say, while in Jail, you might be able to sign up for working, which, there's a catch. You might be able to make money, but your happiness runs down, and you use so much energy the more you work in jail. The working as in Cafeteria, Laundry, Butcher, and so on. All of those jobs that they do in Jail/Prison, lol.

Also: making weapons. People might have their items taken, but somehow there's always people in prison that find a way to make a weapon. Example: Toothbrush Shank. But, also another catch. While making the weapon, a reminder that the person WITH the shank has a 50% chance that they will get caught.

Oh, and another thing: Prison Riots. They might be mentioned before, but it's still a very good idea.

Gang Members: How about..if you're gang member gets caught trying to bust you out of jail, or gets caught for anything else, attacking someone, crimes, or any way, how about you are able to do a riot with them? Getting help from them would be very cool in my opinion. These are just ideas that go along with the topic. =D