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Advice on role-playing on how to deal with bad situations in campaigns
I'm often browsing the internet for answers to interesting questions regarding D&D so when I saw this one I figured it would be useful to some of you and decided to share it, I decided to change a few terms and fix some typos in order to make it easier to understand:

Question: In D&D my players ended up in prison, what should I do to get them out without just saving them at the last minute by some "act of God"?

Murphy Barrett Wrote:Nothing.

It’s not up to you to save them or condemn them. It’s up to them. Presumably, they got themselves in this mess, they can get themselves back out.

Players are really good at messing up plans, to the point where I rarely plan anything anymore. I have intentions. I set an environment, give them an objective, and just let them go. I haven’t bothered to figure out how to “win” any scenario I write in years. I just know what I consider to be the win conditions. Usually, the players agree with me at least on that. But how they get from “take that hill” to “we captured the hill, we’re pressing on into the town” is entirely up to them.

So, the players are in jail. The Bard schtupped a Watch Lieutenant’s favourite barmaid, and he trumped up charges of disorderly conduct, lewd behaviour, and assaulting a member of the watch. Never mind that it was the Lieutenant who was drunk, in plain clothes, and that he threw the first punch. The Players are destined for the noose in the morning.

It’s up to them to figure out how to get out of it. And here’s the important thing. You need to be able to work with what your players give you. Because, if I’m the GM, I honestly have no idea how they’re going to get out of this. I just figure that they will.

So the Bard tries to cajole one of the guards. And rolls a 2. The guardsmen really likes that LT, so fuck you, Mr Bard.

The Rogue wants to look for anything she can use to pick a lock. Well, there wasn’t anything there, to begin with, but she rolled a 20! Turns out some previous prisoner left a partial set of prison-made lockpicks. They didn’t exist until the Rogue went looking. So she picks the lock…and rolls a 1. Not only do the picks break, but the guards are alerted and now they’ve stripped the party down to their underwear because obviously the picks were smuggled in.

At their wit's end, and convinced they’re going to die, the Cleric prays to his god for the souls of his fellows. Now, it’s down to the wire, and damnit, I really don’t want to hang them. So suddenly one of the guards is a follower of the same god as the Cleric. And in this town, they’re not too fond of the God of Tits and Wine. Realizing the Cleric is a church brother, the guard enters the cell, informs the Cleric that GTW is pretty frowned upon hereabouts, and if they’d like to keep their heads firmly attached to their shoulders, he should keep quiet about it. Then, when he leaves the cell, have him remark that he needs to make sure the cell is definitely, absolutely, locked and that he mustn't forget like last time.

Except your players are morons and miss the bait. So in the morning, they’re being marched to the gallows, and the Barbarian decides that now is a good time to make a last stand. He snaps his bindings! He rolls strength and gets…a 3. With a +5 in Strength. DC to break bindings is 15. The fucker. But lo, the rope is old! “Well, you didn’t break the rope around your wrists, but it’s starting to fray, and you’ve managed to startle the guard escorting you.”

Huzzah! He tries to grapple the guard and rolls an attack. You rattle some dice around, not actually caring what they say as the guard “defends” himself. Barb’s hooked his bindings around the guard’s throat and is now using him as a meat flail. Why? Because you don’t want these idiots to die, it’s neat, and everything saner has failed. In the ensuing melee you rattle dice around some more and press the Players just enough that they feel that they’re challenged, yet still escape mostly intact.

Now the key to this improvisation is that you have to work with what the players give you. If they do nothing, well, it’s the gallows then. As long as they keep working the problem, keep giving them things to work with. And damnit, escape by meat-flail is better than anything I’d have come up with myself.

If you save them by DM fiat, either by DEM or Daring Rescue, you rob the players of agency. They didn’t get to make a daring prison break, they were the damsels in distress for some other hero’s story. If you want your Players to feel like the heroes, give them a chance for their wacky scheme to work. Hell, if they want to fly out of the bars like sparrows, let them run around the cell flapping their arms like morons…right up until the Druid’s Polymorph spell finally works. Whatever they come up with, roll with it and give them a chance.

Let them be the heroes of their own story.

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