| Graffiti | Use spray paint on a prison wall | Prison item or action when available | Easy |
| Very Regretful | Use the cry action in prison | Lowers morale; exists for this moment | Easy |
| Show Some Respect! | Win any prison fight | Train combat; pick winnable targets | Medium |
| You Can't Chase Me | Succeed at escaping during a wanted / police chase | Home or travel chase decisions | Medium |
| Jailbreaker | Succeed at the prison escape mini-game | High risk; keep health up | Hard |
| Riot Starter | Succeed at starting a riot | Needs prison reputation at 100 or higher and Prison Life skill at 30% or higher | Hard |
| Gang Leader | Form a gang | Reputation 80+, at least two jail friends at 50+ friendship, and win the initiation fight | Hard |
| Survivor | 30 days incarcerated (counts over multiple sentences) | Stay inside; survive the daily loop | Medium |
| Veteran Inmate | 100 days incarcerated | Long sentence or repeat visits | Hard |
| Smuggler | Succeed at a smuggle mini-game or event | Yard and contraband opportunities | Medium |
| Prison Scholar | Read 5 or more books in the prison library | Choose read options in library events | Medium |
| Brawler | Win 5 prison fights | Repeat yard and combat events | Medium |
| Fight Club | Win 10 prison fights | Higher exposure to injury | Hard |
| Prison Champion | Defeat the prison champion | Random event after 5+ fight wins; not guaranteed immediately | Hard |
| Craftsman | Craft a shiv in the workshop | Gather materials and use the workshop action | Medium |
| Tattooed | Use the tattoo kit | Prison item use | Easy |
| Lawyered Up | Hire a lawyer | Costs 15 gems; sentence must be more than 15 days left | Medium (currency) |
| Early Release | Succeed at a parole hearing | Good behavior and the parole event chain | Hard |
| Took On The Law | Win a fight against a guard | Random guard encounter | Hard |
| Guardian | Defend a friend in a prison interaction | Needs a friend in jail and the right event | Medium |