Exaggerated: Bob is sent to jail to serve a 5-month sentence for jaywalking. When he gets out, he becomes a Serial Killer.
Downplayed: Bob is sent to prison for embezzlement. When he comes out he decides that subtle is overrated and doesn't work, and decides to rob the bank in broad daylight, rather than try to be sneaky.
Bob has spent time with other convicts in there for far worse crimes, and has started to think like them.
Bob is still in "survival mode," and just can't get out of that mindset.
While he was in prison for jaywalking, he lost his job and can't get another one now that no one wants to hire an ex-con. He doesn't have a family to rely on until he can get back on his feet, and he needs money badly to pay the bills. So he feels like he had no choice but to rob the bank.
Bob goes to prison, and comes out fully rehabilitated and ready to be a good, functional, law-abiding citizen.
Bob is sent to prison for a serious crime like rape. When he finally gets out, he makes a habit of committing petty crimes.
Subverted: Bob is sent to prison for a much more serious crime, not a petty misdemeanor.
The crime was helping his girlfriend, Alice, escape from prison, which is a felony, however well-intentioned.
Bob ends up committing even worse crimes (i.e. if he was imprisoned for rape, he becomes a Serial Killer.)
Parodied: The episode is a harsh satire written by critics of the penal system.
Zig Zagged: Bob gets arrested for a string of minor crimes, but manages to plea bargain down to just jaywalking. When he gets out of prison, he decides to rob a bank. But just outside the bank door, he has a change of heart and goes home. There he discovers his wife in bed with another man, and kills them both, landing himself back in front of the judge on two counts of second-degree murder.
Averted: Bob did not go to prison for jaywalking; he was merely fined.
The writers want to find a way to inject some sympathy into Bob's character, so they give him a backstory of having been hardened by the uncaring justice system.
Lampshaded: "First jaywalking and now armed robbery? Bob, I think prison hurt you more than it helped!"
Invoked: Bob meets his cell-mate, a big tough bully who likes to brag about his armed-robbery exploits.
Bob is polite to the guy, but doesn't take any of his "advice." Instead, he just counts the days to the end of his sentence when he gets to see Alice again.
Bob is given counselling, rather than just being thrown in a cell "to think about what he did." The counselling helps him to rehabilitate, and become a truly law-abiding citizen, no matter who he is in prison with.
Prisons are heavily tiered in offences such that first timers don't spend time around hardened crooks and thus prisons can't operate as training houses.
Discussed: "Bob used to be such a nice guy..."
Conversed: "That's the trouble with the penal system. They care far more about punishment than they do about rehabilitation."
Deconstructed: This means Bob will eventually be sent back to prison, and that could put strain on the prison system.