With that said, if any part of your campaign is going to take place in a conventional prison, then you need to front-load that part so you don't get a pipe wrench hucked into your gears.
|What do you mean you got teleport as a supernatural ability last level?|
It Needs To Be A Challenge
Rock and iron prisons are built to keep people inside. However, there are so many class abilities, spells, and other features that a party will acquire by mid-levels that it's just easier to make a prison escape arc an earlier challenge in your game.
Trust me, if you haven't done it by level 6 then it's best to just move on with the rest of the game.
|Hey, new fish! Who you bunking with, huh?|
When all the party has are some starting spells and abilities, as well as improvised weapons and tools, getting out of prison is a tall order. Whether it's locating the secret, monster-infested tunnels below the mountain, making a daring escape over the wall in the middle of the night by combining stealth, magic, and muscle, or just building up enough influence in the cell blocks to unite the gangs and stage a riot that cannot be contained, these things are a challenge when you're relatively low level and have a limited tool box.
By the time you can blast a door off its hinges with a wave of your hand, smash through stone with your bare fists, take control of someone's mind, or pickpocket the keys from a dozen yards away, the challenge of escaping a prison goes down significantly. And if you can just step through a hole in the reality, or turn yourself into a falcon and fly away, it becomes negligible.
More than escaping the prison, though, capturing a mid-to-high-level party peacefully and getting them in the prison in the first place can be nigh-impossible without some serious, hand-wavey shenanigans. When half the party is immune to poison, some can't be knocked unconscious, and some will just refuse to surrender when the bounty hunters or posse comes riding up to them, you've sort of backed yourself into a corner as an storyteller. And even if you do manage to lock them in, how do you keep them there? Anti-magic collars and shackles that block all spells above a certain level? Putting the prison in another dimension so you can't just pop out of it? Covering the walls with anti-magic runes and spell-dead zones so that every necromancer, evoker, and sorcerer in the block doesn't turn the place into an eldritch volcano of pent-up fury?
Can you theoretically imprison powerful spellcasters, iron-fisted warlords, and mind-bending enchanters in places like that? Sure, you can. But it's going to take a lot of time, and a lot of precautions to make it happen, and keeping that balancing act fair takes both some serious mechanics chops, and a lot of luck.
Then there's the question of player agency to deal with...
If It's Going To Happen, Don't Pretend They Had A Choice
Back in Avoid Submission Encounters (They Throttle Player Agency), I made the point that if players don't have a choice in what's going to happen, there's no point pretending they do. If you're just going to throw orcs, will saves, and knockout darts at the PCs until they eventually succumb, and there's no way to run from the fight, then you may as well drop the pretense and just say they're captured, tried, and sentenced in a cut scene.
And if you're thinking, "Wow, my players would be pissed if I just said they were captured, and didn't give them any chance to use their spells and powers to get away," then you're getting the point.
|You say we're surrounded? I say we're in a target-rich environment.|
A first-to-third level party might put up a good fight, but you can capture them through completely mundane means. You don't need to bring in anti-magic containment specialists, backed-up by hulking golems and alchemical snipers. In fact, you can probably narrate the scene with some text like, "The bartender says he has to go in the back to get your brews, but you hear the door lock behind him. A moment later a voice calls out, 'Gray Wardens, we know you're in there. Surrender now, or we will take you!' You fight hard, and leave your share of broken teeth in the street, but eventually they clap you in irons, and toss you into the back of a wagon." As long as you make it clear that they went down fighting, most players would simply accept that, eventually, their second-level barbarian or first-level wizard probably would have gone down under the slew of billy clubs and boot heels coming their way.
Could a low-level party fight their way free? It's possible, but they lack the ability to use a single power, or a couple of chained spells, to completely escape or just eliminate a mundane threat, which is what makes a similar scene happening to a higher-level party such a problem in terms of suspension of disbelief. After all, if the monk can teleport away at will, moving several hundred feet with a single action, then how did the bounty hunters capture him? If the druid can turn into an insubstantial puff of air and fly away, then how was she brought down? If the conjurer can grab the two martial characters and poof them miles away from where they were sitting in the inn, then why were they apprehended at all?
You get out ahead of all of these objections when the party is still low enough level that they don't have access to these tools. Because while they might be impressive by the standards of normal, everyday people, they haven't reached that superhuman standard where it takes a special force of hand-picked NPCs to bring them down, and a specially-constructed prison to hold them.
With that said, if you want your PCs to have to escape from an inter-dimensional jail, or break out of a genie's lock-up, you should totally do that. But as mentioned above, you might want to consider leading with that, instead of trying to find some contrived way for the party to all be thrown into the same prison. You should also work with your players to make sure they bring characters who would logically be in such a place.
Trust me, nothing is more annoying than bringing a guard captain paladin, and being told that no, actually, you're prisoner #57892. Even if you didn't commit the crime you were imprisoned for (a perfect reason to want to escape and bring the real party to justice), players should know they're walking into a prison break scenario so they can construct an appropriate story. Otherwise you run the risk of the game you're running not being the game the players thought they signed up for.
One last thing. If you're looking for a hot tip to get any and all PCs into a prison, then make sure there is something they have to achieve while they're in there. A piece of information they have to learn, a spy they have to break out, or someone they have to assassinate if you're running an evil game. The party then decides to get captured and sentenced in order to bring them closer to their actual goal, which tends to be easier to swallow as bitter pills go, and neatly solves this little dilemma for you. Especially if the PCs are imprisoned under false names, allowing them to hide things about themselves (like their in-born magical powers, for instance), which can be a huge advantage in the coming arc.
Remember To Populate Your Prisons!
A lot of DMs make the mistake of thinking all about the guards and the security when it comes to their holding facilities, but they seem to forget that prisons have, well, prisoners in them. These places are communities all their own, complete with slang, traditions, and cultures that don't exist outside the walls. Everything from gangs and tattoos, to rituals and currency is something you should think about.
And if you need some help seeding the cells, consider these handy supplements by yours truly:
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That's all for this week's Moon Pope Monday. Hopefully you enjoyed the film, and it provides you all with the same sort of inspiration it did me!
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