Have any of your characters ever been to prison? How did it go?

Have any of your characters ever been to prison? How did it go?

I don't think anyone never had a character go to prison, oldest railroading technique in the book.

Actually no, my character and my friend's character ended up in jail because we were put in a sticky situation (an NPC died suddenly without any explanation, we were the only ones in the building) and we absolutely botched our social rolls to not be suspicious about it (along with the fact that I couldn't come up with anything to say to the guards about it), so we were put to jail for a short period until we were bailed by higher-rank characters from our creeds.

And this was DESPITE THE FACT that my friend was the party face, because he just had the worst luck that day altogether. 3 botches in social rolls that day, out of 4 total that were made.

I was playing as a necromancer in my first ever party, consisting of a group of close friends from high school. We were playing a really ramshackle version of D&D since none of us owned any of the actual books. We just kinda engineered a faux-D&D through what we knew of other fantasy material and called it a day, which honestly kinda made it a bit more fun, if a bit (read: a lot) janky.
I was playing as a necromancer, while a friend of mine was a straight wizard. I was the token evil party member and general schemer, while he was a goofball who ran around with a pool cue as his arcane focus and a pair of many-pocketed cargo pants he kept his belongings in. We were in a town that had somehow been afflicted by a curse that made anything become a zombie if it died on their soil. The citizens were anxious, but he local government seemed to take it as a way to keep the unwashed masses under control.
One night, while the rest of the party was out solving problems, us spellcasters were spending the night in an inn (the room we bought with a wooden disc, which is another story altogether) to get back some semblance of utility. Someone breaks into our room and steals the wizard's prized pants.We are roused by the commotion and decide, upon discovering the theft, chased after the scoundrel. It was in the dead of night, so we couldn't exactly tell who had done the heinous act. Either way, before we managed to find the culprit, we were spotted by a city watchman who was making sure no one broke curfew. Upon seeing my friend running around in the middle of the night without any pants on, he immediately arrested us and threw us in jail.

Cont.

I never had a character go to prison but I've had them nearly whisked away by slavers.

So me and the wizard were tossed in prison and left there. My buddy had no spells left, so he was useless. I however, had an idea. I asked the DM how the conditions in this cell were, and he described them as as horrible as they come. No real beds, moldy, rotten wood, small vermin running around, the whole shebang. I asked if I could roll to catch one of the rats, and he said go for it. I managed to nab one somehow and tried to pull the old ketchup-fake-wound trick from Metal Gear Solid using the rat, pretending it was burrowing into my chest. Of course, the guard didn't buy it for a second, so we were still stuck. I resorted to Plan B.
Plan B, of course, was to wring out the rat with my bare hands, raise it's corpse, and send it outside to find the rest of our party and bring them to our aid. Remember, this wasn't using official D&D rules from any edition, so if it sounded cool, more often than not it would work, as long as you rolled successfully. And let me tell you, I rolled successfully.
The rat, whom I had given an affectionate nickname (likely Petey as a reference to Unforgotten Realms, but it has been lost to time), set off to find our buddies, who had been scouting out a sort of gladiator arena north of the city hall that turned out to be where civilians and dissidents were punished if they commit too many or too horrible crimes. The rat sniffed them out and drew their attention to the jail, where they then bailed us out of prison with more wooden discs.
HOWEVER, we unfortunately were not done. As we left the jail, the wizard spotted his cargo pants tightly wrapped around the legs of one of the prison guards. In a massive lapse of judgement, he ran up and pants'd the guard, screaming about how they were his and to give them back.

Now, I don't know about your settings, but in this one pantsing a guard is a crime. And so, our wizard was immediately re-arrested. This time however, he was not put in jail. He was hauled off and put in a wooden crate. He had no idea where he was, but I could find him. I sent the rat to follow the crate, which was brought to the gladiator arena and put in a storehouse nearby. Our wizard was going to be in the pit against god-knows-what. I had my rat start to chew through his crate, but was soon cornered by two other rats.
My little rat was outnumbered, but it didn't mean shit to him. In only a short few turns, he had rolled three consecutive nat-20's and absolutely decimated his adversaries. My rat had become legend. Unfortunately, as soon as he was done kicking the shit out of those rats, he went back to chewing through to the wizard. And this is where things got ugly.
The two enemy rats are zombified as part of the land's curse. In this form, they are much, MUCH stronger than my rat. They then proceed to shitstomp my little rat into the ground so goddamned hard. I lost connection with him after that, and demanded the party we go and break into the storehouse. Not to save the wizard, but for my rat. We were never able to, since the wizard's gladiator fight got in our way. We saved his life, but my poor little rat was never seen again. I miss him to this day. He was what made me fall in love with tabletop games, and he will always be remembered for it.

my character was briefly jailed for buying slaves to feed to my pet dragon

>Brought in for questioning after associating with party member that stole over 5k from the government
>Discovered to be a bugbear (I was disguised)
>All of my shit is confiscated including adamantine sword
>Wait till guards leave my side of the prison
>Break iron bars with bare hands
>Down to bloodied hp, worth it
>Help the other PCs break out
>Beat up guards and grab my shit
>Use adamantine sword to bust a hole in the wall
>Jump into mote below and ride into the night

I had a half orc that ended up in prison twice within a month for crimes he did not commit. A gunslinger in the same world but different camping who ended up jailed once because people thought he was the man who set off a bomb and not the man hunting the bomber.

Then there was my fallout pc who was jailed 3 times for roughly half a year total. Once over a misunderstanding in which he was let out the next day and apologized to profusely by a french Canadian man who barely spoke English. He was later captured by a bunch of crazed anarcho communists when a scouting operation went to shit, got busted out 3 months later when his commanding officer in the brotherhood found out someone went around the chain of command and sent me and my partner on said secret mission. One last time he got captured by aliens who crash landed, got off easy with those freaks because they needed his tech skills to fix tone of their scouting crafts and hybridize some earth tech. Before he new they needed him he tried escaping at which point they realized a man with a mechanical arm and leg was far to dangerous. So they cloned him new ones to replace his long lost limbs.

And now in the most recent game I'm playing a wizard/knight who was thrown into a cell by his older brother for insubordination and arguing with him over a moral dilemma. It was only for the night and because my character's brother had to make a point to not appear weak in front of his men. Actually had a civilized conversation with him when he came to visit me with dinner. That night was also when I and my friend who was playing my character's sister (who was also wizard) found out our brother is a little bit crazy, like actual psychological condition crazy.

He broke out, flayed his captors alive to make a new cloak (they burned his old one when they "caught" him), then tortured a few to death before flying off.

Yeah, when I played as a little car in Monopoly. It was okay.

Yeah. It was a scifi game and we'd all been arrested. My character and his NPC friend were imprisoned after being arrested and buried under the weight of plea bargains from the rest of the party. Fortunately, a civil war broke out six months later and they fought for the government after which they joined the second party.

My character is now moderately afraid of castles because every time she enters one she winds up in a dungeon and something awful happens.

Yes, he tried to survive and go under the radar and not get involved with prison factions.

Yes, there is local law enforcement in most towns. But you have to give them a chance to skirt the sheriff, and make an escape.

Haaaa... as the party face, extracting information from a prisoner in a prison before being extracted himself. Good times.

> The prison brawl almost killed me.

I'm playing nu-wod as a veteran monster hunter from Germany. He raised too much attention from the vampires of Detroit so they framed him for murder. He has the improvised weapon ability, so when someone tried to shank him in the cafeteria he beat them unconscious with a metal lunch tray.
I'm hoping my partner in crime will get me out of prison next session.

My players attacked an adepta soritas because she insulted one of them for flexing. They used fate points to not die.

Yes she got taken to magic prison. Bonus round, they turned her into a magic battery for the entire prison.

My arrogant, haughty sorceress had a thing for the party rogue. We were hanging out with an NPC alchemist who had dated the rogue and still liked her. Within five minutes of the rogue leaving the two of them alone to sneak into the bad guy's hidden lab, they were brawling in the street. And then everyone got arrested.

We weren't in there for too long, the bad guy's grandson came to bail us all out and apologize for his grandfather's behavior, but the scolding the sorceress and alchemist both got from the rogue resulted in the sorceress spending most of the rest of the adventure sulking in her room, and promptly hopping on a boat to another nation alone out of guilt as soon as current obligations were dealt with.