For those who haven't played Jail server:
T's are prisoners, they start in jail cells without weapons.
CT's are the guards. They start with weapons. One CT becomes "the warden" and gives the T's orders that they must follow.
The warden has the T's play various games, with the losers dying in an attempt to whittle their numbers down. The T's look for moments to rebel and storm the CT's. CT's cannot kill the T's unless they have rebelled against the orders, gone somewhere they shouldn't have, or lost one of the games they played.
The last T gets a "last request" which is a sportsman like attempt to let him kill all the CT's in a method of his choice.
The last CT has permission to kill all remaining T's without a reason.
This makes for a unique game environment that is tons of fun and something completely different than your average CS:S experience. If you haven't tried it, I highly recommend that you do.
Oh, VIDEO NEEDS MORE SPITFIRE'D!!!!