D&D: Five Ways To Get Out of Jail Free(ish)

So you’ve been captured and thrown in a Dungeon. What’s an adventurer to do? We’ve got you covered. Here’s how to get out of jail in D&D.
We’ve all been there. Maybe you weren’t expecting the guards to have that good a perception or Initiative. Or you didn’t know that the King was going to be right there when you decided to steal the crown jewels (from his crown, that he was wearing at the time). Or you were perfectly innocent of any crime and how could you have known that the heart of the enemy warlord’s encampment was a restricted area?
Whatever the reason, almost every adventuring party can expect to see the inside of a dungeon at one point or another. Er. But like, the dungeon as in they’ve been thrown in there. Not the dungeon you’d typically loot.
Look, here’s what to do when your PCs get thrown in jail.
The Ol’ Switcheroo
Deception is often a great way to unlock the door you can’t pick/break through/teleport past. We’re taking it as read that you’ve been thrown into a dungeon meant to hold adventurers—obviously if you can just misty step out of there, do that. But if you can’t, one thing you can employ is subtle trickery.
Learn the faces of your guards. Or anyone important, really. Then use magic—or a well-concealed disguise kit (you did tell the DM that you keep your disguise kit concealed on your person at all times, right?)—to assume the guise of another person. Preferably someone the guard on duty could be cajoled into opening the door for. A quick “let me out so we can catch that dastardly (but handsome) adventurer” later, and you’ll be free to walk out of there. A spell like Alter Self is great, because while Disguise Self is an illusion, Alter Self can change your physical form.
Just make sure you’re good at Deception.
Hide So Good They Think You Escaped
If you’re not good at Deception, try Stealth. How, you ask? You don’t have to stealth your way out of the dungeon cell—you only have to make it look like you’ve escaped. The trick is to conceal yourself somewhere within the cell. Maybe you are very good at hiding in shadows. Or maybe you can cast invisibility. Or Meld into Stone.
Either way, all you have to do is appear to have vacated. Maybe for good measure, leave something out of place in your cell before you hide. Like a note. Or a pouch of gems. Or whatever you have that might encourage the guard who sees that your cell is empty to unlock the door and open it so you can ambush them.
It’s honestly even better if the whole party can’t pull this off. They can help sell the idea that you’ve escaped by complaining to the guard. And suggesting that if they don’t open the cell to see how, the warden might be real displeased with them.
Fake Your Own Death
Along the same lines of hiding—you can fake your own death. A Feign Death spell, or just a really good Performance/Deception check, might help you pretend to have escaped via shuffling off this mortal coil. After all, who needs to imprison a corpse?
When they open the cell to come and collect your body, again, ambush. Or if there’s plenty, you can keep playing dead until they haul you off to a casket or something and then escape once everyone thinks your dead. Which has the added benefit of making it much less likely anyone will come looking for you.
Just make sure there aren’t the bones of prisoners who have been tossed down into the dungeons and forgotten about in the cell with you—otherwise, this one might not work.
Secret Tunnel
It worked in Shawshank Redemption. It can work in your D&D game. You might have a Move Earth spell, or the ability to Wild Shape int a creature with a burrowing speed. Or maybe you’re just very determined and have a digging implement or adamantine spoon. People have dug their way out of some surprising places in the real world with surprisingly little.
This is the sort of brute force option for all your Strength characters out there that can’t convince your DMs to let you bend bars and/or lift gates.
Make a Suggestion
Finally, magic. Magic is the answer to any problem in D&D. And the new version of the Suggestion spell is going to be an indispensable source of shenanigans. Make a suggestion that takes no more than 25 words, something like “open my door, then go home and stay there for the rest of the day” and if your target fails a Wisdom saving throw, they are magically compelled to obey your suggestion foor the next eight hours, as long as you can maintain concentration on the spell.
It’s surprisingly effective. But risky. Best to try and stack the odds in your favor before you try and pull something like this one off.
So now you know how to get away *from* it when you don’t get away *with* it!
