Stealth in Dungeons and Dragons

Wrestling with Randomness in TTRPGs

Last night, I stepped in to DM a low-prep one-shot session focused on stealth in Dungeons and Dragons. Our regular DM was out, and I had little time to cobble something together that needed to last about three hours. I sketched out a loose mission with flexible challenges and kept the approach as open as I could. There were a few rails to keep the plot moving, sure, but I made sure to leave room for real player agency — I’ll add a link to the actual adventure once I’ve polished it up a bit with my lessons learned from running it.

The adventure I ran was called A Stitch in Amber, a Feywild-themed infiltration one-shot for Dungeons & Dragons where players had to rescue a kidnapped mapmaker from the web-laced camp of the Mantid Matron. I created a series of encounters that gave the players the choice to use stealth, deception, or combat to achieve their goals. Each time, they chose to start with stealth. But if I’d relied purely on the d20 dice rolls, there was no way they could have pulled it off.

One early challenge involved retrieving resin “goop” from a bubbling pool. The idea was to coat themselves in the stuff so they’d smell like hive members and blend in — a classic scenario involving stealth in Dungeons & Dragons.

Then came the rolls.

The players kept failing their stealth checks. Suddenly, they triggered a trap and were completely exposed. It was meant to be tense, but instead, the dice made it feel clumsy. Not because the players chose wrong, but because the system offered no grey area. This is one of the common pitfalls of stealth in Dungeons and Dragons: the risk of a single failed roll derailing the entire plan.

And just like that, the story shifted into combat. Not because anyone chose violence. But because randomness left us no other door.

I’ve Always Known This Was an Issue…

Honestly, I’ve always known the D&D d20 system has a bit of a fragility problem, especially when the dice aren’t in your favor. That single-roll pass/fail mechanic can be brutal.

But last night reminded me how awkward it can feel when a compelling idea or a thoughtful player choice is shut down by one bad roll.

It wasn’t a failed plan, it was a failed number.

And in a narrative-driven tabletop RPG, that just feels clumsy.

Rethinking What Failure Looks Like in Dungeons & Dragons

Dice are great at creating uncertainty, but they don’t always serve the story when they act as a hard binary gate. Especially in a one-shot or fast-paced arc, failure needs to be more than a dead stop.

What could I have done instead?

A failed stealth check means you make it in, but a clue is missed, or you’re spotted later.
The rogue succeeds, but the fighter lags behind, creating tension or a split path.
You’re not discovered, but you leave signs, and now someone’s on your tail.

These are all ways to preserve tension and keep stealth in Dungeons & Dragons from feeling like an all-or-nothing gamble.

That shift, from pass/fail to cause/effect, makes failure a storytelling tool, not a dead end.

Dice, Drama, and Pacing in Tabletop Roleplaying Games

Dice can also mess with pacing, especially when they kick off combat scenes you didn’t intend, or stall progress during key story moments in your TTRPG session.

If a single roll suddenly throws you into a long tactical slog, you’ve gone from mystery to math without warning.

That’s fine when it’s intentional. But when it’s accidental? It’s frustrating for everyone.

Tools for Story-First Dungeon Masters

If you’ve ever felt the dice betray the vibe, here’s a few ways to keep the story in your hands:

Fail forward. A failed roll should introduce complications, not end the scene.
Reserve rolls for real stakes. If failure isn’t interesting, skip the dice.
Use failure as future setup. Missed stealth could mean consequences two scenes later.
Stay flexible. Let the players’ intent shape the outcome, even if the method changes.

These techniques help smooth the rough edges of stealth in Dungeons & Dragons, keeping gameplay cinematic and player-driven.

The Dice Aren’t the Plot

That one-shot wasn’t a disaster. The players rolled with the chaos (pun intended). But I walked away with that old familiar feeling: I gave the dice too much control.

The dice can color the world. Twist it. Complicate it. But they shouldn’t close doors the players were just beginning to open.

So next time I’m running a game around stealth in dungeons and dragons I won’t let the story die on a d20. I’ll make it veer. Linger. Echo.

Because the real game? It’s in the telling.