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Running Heists in D&D

by Mike on 10 January 2022

Previous articles describe troublesome quest models and how the Seven Samurai quest model fits well into our D&D games. The heist is another useful quest model fitting well with the style of our D&D games. Today we're going to look at running great heists.

Patrons of Sly Flourish can watch a video in which Johnn Four and I talk about running great heists in D&D as well as three other videos on running situations and the five room dungeon, running mysteries, and thoughts on RPG map designs. Find out more at the Mike Shea and Johnn Four video collaboration page.

Great Situational D&D

Heists follow a general model of D&D that often works very well — building situations. Instead of building adventures room by room and encounter by encounter, we consider a whole location with multiple entrances, multiple paths, and multiple ways to engage with the location and the inhabitants moving within it.

The heist is one such situation built from a number of components:

Heists also work well by running our game in two phases: the plan and the execution.

The Target

The target can be just about anything in our heist scenario. It might be a physical object. It might be a piece of information. It might be a person, willing or unwilling. It might be a dream or a memory. The movie Inception is an example of a heist involving dreams.

When running heists, it's important to declare what the characters seek up front and not to change it during the execution or it can feel frustrating. No, Mario, your princess is not in another castle.

The Location

The target sits in a location and certain locations lend themselves to great heist adventures. Locations work best for heists when they have the following criteria:

Justin Alexander's descriptions of Jaquay-style locations often work well for heists and many of Dyson Logos's maps fit this style.

In particular, manors, keeps, and castles work well for heists, especially those with underground tunnels, cellars, and other interesting ways in. The haunted manor in Sinister Secret of Saltmarsh from Ghosts of Saltmarsh is a good example of a great heist location, as is Vanthampur Manor in chapter 1 of Descent into Avernus and Gralhund Villa from chapter 3 of Waterdeep Dragon Heist.


Instead of populating locations room by room, consider the total force that occupies the location. Who are the guards? How many are there? What is their typical behavior? What monsters guard the secret locations or underground passageways? When we think about the overall force protecting the target at the location we can recognize how they act and react as the characters infiltrate the location.

We can also populate our location with non-combatants. Who populates the location that isn't really involved with protecting the target? They can add fun complications and roleplay opportunities while the characters move through the location. This is a great tip I picked up from Johnn Four at Roleplaying Tips.

Phases of Play

When running a heist, consider breaking down gameplay into two phases: the plan and the execution.

We want to give the players ample time to look at the situation, maybe even giving them a copy of the map of the location if it makes sense that they'd have it or give them a mixture of reliable and unreliable information. They might spend time reconnoitering the location, learning what they can and using this to aid in their plans.

We likely want to limit how much time the players spend on this or they'll get caught in decision cycles that go on forever. Limit the amount of time they spend on it to 30 minutes or so. It's an out-of-game limitation but one that helps move the game forward.

The second phase is execution in which the characters conduct their heist. This plays out like a traditional situational D&D game. The characters do what they do and the world reacts.

Avoiding Single-Roll Failures

When running heists, we don't want the whole heist to rely on a single roll for success or failure. Instead, each roll moves the situation forward either positively or negatively. Complications can still occur even if every ability check succeeds and success can still occur even if every ability check fails.

The excellent RPG Blades in the Dark is built around running heists and uses "progress clocks" to manage multiple successes and failures as situations evolve. A progress clock might require a number of successes before a full success occurs or might create two opposing clocks, one for the characters and one for those guarding the target. Instead of establishing progress clocks ahead of time, we can improvise progress clocks as we think about the approach the characters are taking and as the situation evolves.

Here's a YouTube Video on using progress clocks in D&D.


Complications are a fun way to change up the nature of a heist as it's happening. We don't want to drop in too many complications or include complications so big that the entire plan falls apart. Here are some example complications that might occur during the heist:

A Powerful and Flexible Quest Model

Heists are an excellent and flexible quest model for our D&D games. By changing up targets, locations, and inhabitants we can re-use this quest model for many different games, each resulting in a unique story we can share with our players. Add the heist model to your bag of tricks and you have a flexible model for some awesome D&D games.

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This work includes material taken from by Michael E. Shea available under a Creative Commons Attribution-NonCommercial 4.0 International license.

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