• Courtney Barkley

Characters in the Clink: Handling Prisons in Dungeons and Dragons

It’s inevitable in almost any tabletop RPG game -- the characters are going to involve themselves in some shenanigans.

Sure, some of them may be innocent pranks, but the draw to step outside the bounds of the law in a fantasy environment is real, and plenty of parties succumb to that temptation… or just end up on a runaway train of unexpected events that land them on the wrong side of the law.

When you’re the Dungeon Master (we call them Quest Masters), you get to decide what kind of in-world consequences the characters will have to deal with. If they’re out in the countryside, perhaps no one will discover the evidence of their crimes until it’s too late. But if they’re in a town, chances are they’ll end up thrown in prison.

So what happens after you lock them up?

Justice Systems

In order to know how to deal with your players’ transgressions, you’ll need to have a justice system in place. Can the constable throw them directly into the prison? Will they see a judge or other lawmaker first? Is the law of the land rigid, or is there some leniency allowed? Are there certain crimes (blasphemy or treason, for example) that might carry heavier sentences?

These things are important for you to know, not only because they will help you determine if the characters make it into the prison to begin with, but also because it will have a lot of influence on the prison itself. Is it a small two-cell building or a large complex in the center of town? Do they have time to try to formulate a plan or is their execution scheduled for an hour from now?

These are all things your players can discover with some local knowledge or by asking the right people. Speaking of people…


Here’s where you get to really have fun. Fantasy prisons are the perfect background for introducing the wildest NPCs you can imagine. You could go anywhere from dark and dangerous to absurd and ridiculous when it comes to your players’ fellow prisoners. Will they meet someone who is willing to help them out, or perhaps someone who will foil their plans to gain favor with the guards?

When it comes to NPCs, you’re not limited to just prisoners! You also have guards and bureaucrats to play with. The guards can be anything from straight-laced loyalists to completely corrupted. From the NPCs who process the characters upon entry to judges and lawyers who handle their trial (if there even is one), there are also plenty of opportunities to work some bureaucrats in.

Much like the guards, the paper-pushing characters can be obstacles to your players’ plans or even an instrument in helping them craft their escape.

The Escape… or Not

So you have your basic justice system and NPCs -- what now? Well, in large part this will be up to your players. It is wise to have a few courses planned out ahead of time to cover as many bases as possible. A few you might want to consider are:

  • Jailbreak: The party doesn’t want to wait to hear a verdict, and who can blame them? In order to play out a potential jailbreak, you’ll need to know the basics of the prison’s structure. Plan out what sort of cell they’re in, and if they’ll be separated or kept together. Have an idea of what sort of obstacles you’ll put in their way beyond the basic guards and locked doors. Are there any hidden traps or magical alarms?

  • Bribery: This tried and true method gets players out of all sorts of trouble, but it’s also easy to subvert if you want to make life a little harder -- simply have all their money and weapons confiscated upon arrest. If you choose to leave it an option, though, having the players make insight checks to see which guards might be susceptible to a little palm-greasing is a great way to get that started.

  • Playing by the rules: If you have a party of lawful goods (or even just a bard with a lot of faith in their high charisma stat) your party might choose to try to talk their way out of the prison by following the rule of the law and going through whatever trial the local justice system requires. In this case, it can be helpful to have a bit of a script prepared. After all, these officials likely hear cases every day, so they’ll have a spiel they use to start things off, at the very least.

As the Quest Master, you get to decide the law of the land, as well as how that law is applied in each city, town, and countryside your characters travel through. When your players break the law, they’re offering you a unique opportunity to see exactly how they’ll handle a prison.

With a little creativity, a prison session can be a fun romp or even an emotional turning point with lasting impacts on player characters. With the chance to set some strict bounds in place -- locked in a room with no supplies -- you can enjoy watching your players scheme and get creative in ways they might never have considered before.

Have your players ever been thrown into prison? How did they handle it? Let us know in the comments below!


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