Squat brown-bricked building. Four lumpy corners, small courtyard for “outside” time.
 At the bottom of a huge quarry pit. Can only get in or out via pulley basket, no need for cells.
 Underground, built into a refurbished cavern. Cells are just dead-ends with bars over the front.
 Tall, gray structure. Everything in the prison is in this one square building.
 Large camp with communal wooden houses, several layers of walls and fences protect it.
 It's on an island, built into old ruins. Prisoners can roam around, but must return to cells in the night time for role call or else they don't get any food. Monsters eat some of them, naturally.
 Huge iron bird-cages built over the rooftops of a sprawling fantasy metropolis slum. Locked trapdoors allows guards to enter or leave. Even if you slip out you'll just fall to your death.
 Built into a huge black wall; patrolled by soldiers. Defends the border of the land. Prisoners will almost certainly be given some improvised weapons and act as meat shields during invasions.
Who are the Guards? - 1d10
 Hobgoblins. The prison is very well organized and has a strict schedule and uniform.
 Dark Elves. They rule mostly through fear; punishments are harsh and terrifying.
 Orcs. Prisoners are required to do quite a lot of physical labor, the guards are all getting fat.
 Minotaurs or other herbivore beastmen. If you ask for meat in your rations you get beat.
 Gnomes. They use illusions, mirrors, and magical spells to instill order despite their size.
 Rat-Men. They are the best at finding smugglers and escape-routes; notoriously corrupt.
 Dog-Men. Proud, good noses to sniff out contraband, but a little gullible.
 Elementals. They are silent, following preset routines. Lightning elementals shock rioters, water elementals push them back into their cells as well as fill the canteens, etc.
 Humans. It's pretty normal, but they have very little idea with how to punish other species besides humans. “Oh an Elf stole from the larder? Uhh- don't let him hug a tree for at least a week!”
 Meat-Grinder Men. They're “living” people who have gotten torn up so much and put back together that they have mismatched body parts and skin patches from other mixed up guards. They are animated by a magical force, and cannot leave the prison anymore without falling apart.
Why are people sent here? - 1d8
 Political prisoners and inconvenient noble heirs.
 Debtors' Prison. 10,000c or more. Prisoners brag about their high interest rates.
 For being a savage, naturalist, or nudist. Tribesmen are sent here to be 'civilized'.
 For their own protection, but it turns out being in 'custody' isn't what they thought.
 Just regular, run of the mill criminals. The guards segregate the prison based on gang allegiance.
 Those marked by a special blue tattoo, which is cast by a Wizard curse. The curse doesn't do anything except give you a tattoo, so normal law enforcement does the work to send you here.
 Captured soldiers, waiting to be ransomed. Unfortunately, their home countries have probably run out of money in this point in the campaign, or maybe they don't even exist anymore.
 Religious Offenders. Priests who were corrupt, or just people who sneezed into the altar-bowl. This prison treats lacking faith and criminality as equal causes of incarceration.
How cruel is the punishment/general atmosphere? - 1d6
 Relaxed, laid back. Prisoners sometimes get day leave passes.
 Constant aid from outside organizations, such as healers or educators.
 Guards are neutral, even empathetic, but no nonsense.
 Strict and high tension. Riots and murders happen too often for comfort.
 Everyone is very professional, except for one cruel, malicious guard who is too well connected to be removed from his post. Punishments range from public humiliation to mutilation.
 Hell on Earth. Daily beatings, prisoners are rarely fed, prisoners prey on each other as much as the guards. Prison is occasionally bricked-in to starve off all the prisoners to get in a fresh batch. Warden is an actual demon, feeding on the suffering and pain.
Who is your Cell-Mate? - 1d10
 Verto. He's an elf serving a long sentence more out of curiosity then anything. Plays violin.
 Half-elf with some magic, needs protection. Blonde, thin, and young. Likely prison bitch.
 Three gremlins. Were arrested while in a trenchcoat, imprisoned as one. Argue all the time.
 Human villager, son of a leatherworker. Claims he's innocent. He is.
 Priest of the God-In-The-Walls. He's of a savage race like a gnoll, tribal orc, ape-man, etc.
 Runaway Princess, hiding her identity. Can heal curses and diseases with her kisses.
 Half-Back. An awful hunchback mutant, technically a prisoner but works too. Gets free reign around many places in the prison and can get you into the kitchen, morgue, or guardhouse.
 Little goblin, can't tell if it's a boy or a girl. Has a coat full of contraband and always willing to make a deal. Has two of the biggest dudes in the prison as bodyguards if you try anything.
 Centaur. Claims to have been a pirate once. Being stuck in a small cell with a centaur sounds terrible, but he actually gets the biggest cell in the place with a nice window.
 Lady-Killer. Half orc with an anger problems. Real quiet, good with a knife. Supposedly killed a prostitute, but that's not what he is in jail for.
What's the hottest Contraband going around? - 1d12
 Tengu Firecrackers. You need them for the big, banned holiday. Only two weeks away.
 Blood-Dust Shivs. They melt when they touch blood, leaving little evidence.
 Guard “Passes”, paper slips that you give guards to avoid a beating. Sold by guards, obviously.
 Soap, socks, and blankets.
 Scrolls of Magic Mouth. The gangs are using these for fast, secret communication.
 Lotion. It's being used to treat a communicable skin rash going around the prison.
 Key Charms. If snapped, they give the user very vivid daydreams of escape and freedom.
 Lil' Green Snakes. They're harmless, people just want to keep them as pets.
 Salt & Spices to sprinkle onto bland prison food.
 Rustmold. It grows on the cell bars in the damp parts of the prison. Scrap them off, dry them out, and then smoke them for a feeling of euphoria. The occupants of these cells is hotly contested.
 Alcohol. Common contraband, and all of it here is being bought up or stolen to a single gang leader. It's not being drunk, actually powering a little dwarven digging automaton for escaping.
 Brickback Chiggers. Little mites that burrow into the skin and itch the hell out of people. Used as a practical joke, but the prisoners don't know that 1 in every 10 people are deathly allergic.
What Weapon does the Warden carry to instill Fear into the Inmates? - 1d6
 Sexy fetish whip.
 Long curved razor, facial scars are given to the worst prisoners or those about to be executed.
 Magic Crossbow with shock bolts. Doesn't kill, but painfully paralyzes you for an hour.
 Mancatcher. The long pole has a button to switch neck-sizes it can wrap around.
 Syringe-slingshot tranquilizers. Inmates hit too often with it start to drool and become stupid.
 Croquet mallet. Just beats people over the head with it, despite its refined appearance.
A Riot has broken out! Why was it started? - 1d8
 Started by a Gang Leader. Wants to use riot as distraction to kill the warden.
 Started by a Gang Leader. Wants to use riot as distraction to kill another prisoner.
 Prisoners just found out that a vampire has been feeding on them at night.
 Minor Earthquake opened a crack in a wall or fence. Chance to escape if you get to it.
 The silent ogre prisoner in solitary had his little stuffed toy taken away. He's on the warpath.
 Rebellious prisoners are partying; they just want to break into the pantry and liquor cabinet.
 The same meal for the past two weeks has been served in the cafeteria.
 The guards actually started it. They're bored and want to bust some skulls.
How do People actually get released from the Prison? - 1d6
 On good behavior.
 Due to an outreach program.
 By a pardon from a powerful official.
 The prison will close down due to complaints. All inmates are released for suffering enough.
 By serving every single day of your sentence. Not a minute earlier.
 Not a chance in hell.