As a Dungeon Master, there’s one particular style of quest that I have a real fondness for, and that’s heists. Every single campaign I’ve ever run has included a heist because I feel it showcases all of my favorite parts of D&D. You’ve got downtime planning, social interaction, stealth, chases, and even combat if everything falls apart. Maps play an important role, but not just as a way of showing location, but as something the players can interact with in-character as they plot out their strategy.

But as fun as heists are, they do take somewhat of a specialist approach. In this article I’m going to share with you some of the tips and tricks I use for running successful heists in my D&D games. Using the Maps tool at my disposal on D&D Beyond, I’ll walk you through how I set up the The Stygian Gambit one-shot from Keys from the Golden Vault.

Spoiler Warning: From this point on there will be spoilers for The Stygian Gambit adventure.

Top Tips for Running a Heist with Maps

1. Give the players a copy of the map that they can draw on as part of their planning.
2. Use features such as token borders and Draw in Maps to mark key NPCs and the patterns of their movement.
3. Give the players limited information, but reward planning with more intel.
4. Use initiative and longer turn lengths such as 1 or 5 minutes for slow-paced situations where the order of actions still matters.
5. Passive checks are a useful tool when the players have the time to take things slowly.

Give Players Their Own Copy of the Map

Virtual tabletops, such as D&D Beyond's Maps, are a great way to share the location of monsters and player characters in real time as the party explores an environment or tries to survive a brutal combat. However, I like to use them in a second, more diegetic* way—as in-world maps that the characters are using to do their planning on.

* Diegetic is a term to mean that something is present in the world of the fiction itself. Usually used when talking about music to describe songs that are playing for the characters to hear, in the context of D&D it describes things that exist within the world itself rather than outside of it such as the dice or character sheets.

When setting up The Stygian Gambit on Maps, you can select Keys from the Golden Vault under the adventures section. Scrolling down to The Stygian Gambit section, you’ll see two maps, one for the DM that includes labels and secret doors, and one for players that has that information hidden.

Normally, you’d only add one copy of the player version of the map for once the players start exploring, and potentially fighting. However, for heists we’re going to add two copies, one for typical token position sharing and one for the most important part of any heist: planning.

The planning version of the map will be made visible to the players during the setup stage of the heist for them to use as if the characters were looking at a map in-world. During this stage of the one-shot, the Draw and Ping tools will be the most useful.

Using these tools, the players will be able to lay out their strategy and communicate ideas for the heist. As a DM, seeing what the players have in mind can be a vital tool as it allows you to shape the adventure to help the players' plans go as expected; I believe that the DM should be the players’ biggest fan and work to help them succeed while keeping the game challenging.

In addition to Draw and Ping, the Fog of War tool is invaluable for heist planning. Many times in a heist quest, the players will be given a rough or incomplete map and you can accomplish this using fog of war to conceal details the characters would have access to.

Left is the DM view of concealed areas and right is the player view

During the downtime planning of the heist, you can give the players opportunities to reveal areas of the planning map through various small sidequests. Perhaps the architect who designed the casino can be bribed to reveal the layout, or a locksmith who worked on the security could be helped out in exchange for knowing which doors are locked by which keys.

Mark Up the Battlemap with Player Information

Once the heist begins and the players are moving on the target, you can use a shared battlemap not just for tracking position but to display useful information that the characters could observe. One piece of information I like to track on maps is the routes traveled by guards as they patrol. Once the players take the time to observe a guard and their movements, usually combined with a successful Perception or Investigation check, I’ll make the guards route on the map so the players can anticipate their future movements. Using a combination of the border color and Draw tools, you can mark a guard's route and its corresponding guard token.

By adding information to the map as the players explore and interact, you can build up a strategic tapestry to help the players pull off the perfect heist.

Use 'Heist Turns' to Track the Order of Events

The final tool I keep in my arsenal for running heists is what I call "heist turns." This is a way of using initiative outside of combat, but instead of each round being about 6 seconds, they’re about 1 minute. This helps with tracking the order of events as the players explore the target location and is also useful for things such as guard movement detailed above, or if the players have a window of time to pull off the heist. If at any point a fight breaks out, you can even keep the current initiative order but just switch from 1 minute turns to the standard 6 second turns.

When using heist turns, I like to keep all creatures' speed per turn the same as this translates the average 30 feet per turn from 5 feet per second to 1/2 a foot per second, which is a reasonably leisurely pace for a non-combat situation. However, all other abilities use the normal duration, meaning that an ability that uses one action, for example, still only takes around 6 seconds and as such could be done 10 times in one heist turn.

Heist turns are a good example of a situation where passive checks are useful. With a more sedated pace, the players have time to take things slow and carefully, and as such it doesn’t always make sense to call for a roll. But remember that it still can make sense to call for a roll if the consequence of failure is immediate and dramatic.

Say there’s a locked door that is warded with an Alarm spell; failing to pick the lock could set off the spell which would summon the guards. In this situation, where there’s only one attempt possible, calling for a roll would be the appropriate course of action. However, if that same lock wasn’t enchanted and the players could try over and over, using a passive check helps avoid unnecessary rolls and also plays into the atmosphere of carefully planned out actions.

So That’s The Plan

These were some of the tricks I used when setting up a heist one-shot using Keys from the Golden Vault and D&D Beyond Maps. Hopefully they prove useful in staging your own carefully orchestrated heist adventures.

Davyd is a moderator for D&D Beyond. A Dungeon Master of over fifteen years, he enjoys Marvel movies, writing, and of course running D&D for his friends and family, including his wife Steph and his daughter Willow (well, one day). They live with their two cats Khatleesi and Mollie in the south of England.