• Josh Grace

Stealth Checks: The Art of Going Unnoticed

You came here for some tips on using Stealth checks, so let’s talk for a minute about heist movies.

As someone defined them on Wikipedia, heist movies follow the “planning, execution, and aftermath of a theft.” They almost always involve a group of criminals. The criminals are almost always trying to steal something one might consider relatively well-guarded. And the films—when they’re good—are worth watching because of how the characters anticipate and react to the problems they encounter during their heists.

Or to break it down a different way—we have a group of characters trying to go unnoticed as they infiltrate a location to get away with an item.

In Dungeons & Dragons, characters aiming to get into places unnoticed will often try their Stealth checks (sometimes with extra help from the Deception skill). But what does this really mean? What should it mean? And what is the best way to handle the skill at your table?

These are real questions, because as Dungeon Masters (we call them Quest Masters) we can too easily find ourselves running Stealth as the single, binary, pass-or-fail, dice-driven tests outlined in the rules… when what we should be doing is thinking of how the effort to circumvent watchful gazes can play into the larger story of the characters’ efforts to achieve their overarching goal.

When we only say that a high Stealth result succeeds—and shortcut the details—or that a low Stealth result fails, we’re racing right past the check’s inherent drama. And what is that drama? Well, we have our model in heist movies: planning, execution, and the aftermath.


The planning phase of a good Stealth check doesn’t begin with the players; it starts with you, the Quest Master.

First of all, know your group. If you run the same group over and over, you ought to be able to answer such questions as, “Will I ever need to worry about Stealth checks?” If the answer is, “Nope, my party consists of five Barbarians and a Wizard who’s literally never cast anything other than Fireball,” well, you probably don’t need to spend a good deal of time worrying about how they plan to circumvent the guards. Most likely, they view the guards as undercooked XP.

On the other hand, if your group is the sort that wants to consider the multiple angles of—and numerous possible solutions to—every problem they encounter, they’re likely to consider their chances of sneaking around unseen. Especially if any of their names are Rogue, Halfling, and/or Bard who likes to cast Invisibility.

The second step is to set the scene. If you know your group will use Stealth, or you believe a Stealth check is likely, you’ll want to envision the terrain, the surveillance, and the position that the characters might gain via their Stealth. The work you do at this step is the difference between saying, “Okay, you pass at your Stealth check and sneak from the woods into the castle,” and saying, “Okay, you successfully use Stealth to weave through the trees down to the edge of the road, putting yourself into position to roll out and grab onto the underside of the caravan’s lead wagon as it passes.”

The first example is the over-broad, oversimplified use of Stealth we’re trying to avoid. The second example suggests the sort of Stealth check that demands planning—planning that accounts for a detailed understanding of the challenges ahead, that considers available options, and that understands the check is only part of a larger plan.


This leads us to the execution of the Stealth check, and the goal is to allow players to use the skill in a fashion that is both fair and that lends additional suspense and drama to the ongoing narrative.

Like the characters in a heist movie, the characters in your campaign who hope to bypass one or more obstacles with their Stealth skills will expect they have a clear understanding of the challenges they’re facing. They shouldn’t be surprised by the sudden appearance of daylight as they step out of the woods and into a clearing that wasn’t in their path just moments earlier. If they’re trying to weave through the woods, from tree to tree, in order to avoid notice by the watchmen on the ramparts—and especially if they scouted the woods earlier in the planning phase—they should know how close they can get to the castle before the woods end. If the woods end at a moat, your clear and consistent description of the castle and environment should have alerted your players to the idea that the first Stealth check will get them to the moat, but then as they hope to cross the moat, they’ll need both a means across and another Stealth check as they cross it.

And this is key to the idea of getting more from your Stealth checks: You need to help your players think of Stealth as a tactic rather than a strategy.

While the overall plan—or strategy—may generally be to take a “stealthy” approach through the woods to the south end of the castle where the characters can vault the moat and scale the castle walls, each step of the plan is a tactic. This is important because tactics may often change, even when the larger strategy remains in effect. And changing tactics are what the execution phases of good heist movies are all about—how the characters deal with surprises and failures.

We don’t want to change the forest outside the walls, but if we’re expecting a good deal of Stealth, it’s good to introduce surprises in places where they make sense. Perhaps one essential part of the characters’ plan was to bribe a guard to let them in or to leave a door unlocked. Perhaps one of the characters had infiltrated the castle in disguise and had left a door open herself. But when the characters get to the door, it’s closed. The bribed guard was sick, or someone just discovered that the door was open and locked it. Now, the characters have to get through the door, and they need to do so quickly and quietly, adding some tension to the Stealth check they make to stay unnoticed while the Rogue picks the lock.


The aftermath in a heist movie typically comes at the end of the heist. The result of a Stealth check, however, should come at the end of each check—even and especially when the characters have not yet achieved their goals.

Drama requires stakes, risks, and consequences—which rather neatly correspond to our planning, execution, and aftermath phases. Without the consequences, then, there’s no real drama, even if the stakes are high and the characters are taking tremendous risks.

It’s up to us, as Quest Masters, to complete the loop of each Stealth check by making sure the consequences are felt. We can do more than merely tell the players that their characters get into the castle unnoticed. We can help them appreciate their characters’ anxiety as the guards atop the ramparts point and look out over the forest, staring into the twilight for several moments before shaking their heads and turning away. We can challenge them to incorporate their Stealth checks into larger strategies that also account for the Athletics to vault the moat and scale the wall, plus the Deception and Persuasion required to establish a contact within the castle. And we can surprise them with reasonable disruptions to their plans, forcing them to think on their feet.

When we do these things—when we transform a simple die roll into an event with planning and execution—we need the conclusion to reward the build-up.

In the case of the Stealth skill, however, success is defined in terms of people not noticing you. But when the success of a check is determined by the absence of a reaction, that’s not terribly dramatic. Instead, you can reward your players’ successes by describing all the things their characters get to see other people and monsters do because they think no one else is around.

As your players’ characters slip unnoticed into the castle’s basement hallways, they might overhear soldiers griping about the captain’s early morning drills that all the guards are required to attend. Or they might hear a couple of cooks whispering about how one has secreted a key to the liquor storage. Either way, slowing down and allowing your players to enjoy the rewards of their characters’ success feels like a moment come to life, and the characters might even be able to make use of what they’ve learned.

Alternatively, you can revisit what failure means, especially if you’re adding more steps to the process. A character that fails a Stealth check while trying to sneak past a sleeping hydra may, for instance, not merely rouse the beast to attack, but may bemoan the fact that it tosses and turns in its sleep to cover up the object the character was hoping to steal.

Everything Revealed at the Very End

In summary, the best Stealth checks function like the actions in a heist movie. They build on planning, take shape during a period of execution, and come with real consequences in their aftermath.

That said, here are a few quick and easy things to remember as you think about how to make Stealth checks sparkle in your adventures:

  1. Build a world rich enough that it allows for planning. The players should think of Stealth checks as part of their effort, but not the whole plan. They should have a clear enough understanding of the challenges before them that they weave their plans for Stealth into a broader strategy.

  2. Allow for surprises during the execution phase. What if their failed Stealth check doesn’t ruin their plans because no one’s waiting at the post the characters expected to find guards? What if the guards are already dead? What if the characters who hoped to sneak into the castle and then Teleport out of it learn, instead, that the chambers they need to infiltrate are warded by an extra-dimensional interference that will prohibit their teleportation?

  3. Take time to make the consequences felt. Success or failure is not enough. Stealth is all about the way others react—or don’t react—to your presence, so make sure your players are able to enjoy those reactions (or the absence of reaction).

In the end, if you play it right, what’s the score? You’ll run adventures in which your players feel their actions matter more, your scenes will be more vibrant, and your group will better enjoy and remember their efforts to sneak around unseen!

How do you handle stealth in your Dungeons & Dragons campaigns? Let us know in the comments below!


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