With Dungeons & Dragons: Honor Among Thieves hitting theaters and Keys to the Golden Vault landing on bookshelves, now more than ever is a great time to explore heist-themed campaigns and one-shots. While there are plenty of options available in the Roll20 Marketplace, if you’re looking to cook up your own adventure you need to keep a few things in mind. Whether you take inspiration from movies like Ocean’s Eleven and Inception, or draw from real world capers, there is almost always a basic format in place when designing a heist. Of course, exceptions to the rules exist as do heist stories that subvert tropes, but you’ll want to know what’s expected before you dive into changing the narrative.

The Setup

Every good heist begins with the setup. Usually this involves a criminal mastermind. Whether it’s an NPC quest giver or someone in the adventuring party who gets a lead on a job, this is the character who brings a crew together to get the job done. In the case of an NPC, there’s an added complexity of whether they’re a trustworthy source. The stakes need to be high for a crew to agree to work for a shady quest giver. 

The Crew

What’s important to remember in the crew is that each character must add something to the ensemble. For the heist to work each member of the crew needs to have a key role. These roles are varied enough that any well-rounded adventuring party could fit into them easily. Besides the leader, the crew is made up of:

• Thieves: con people, distractions, bait, burglars, safe-crackers, and pickpockets.
• Technicians: gadget makers (artificers), mission control (using sending stones, clairvoyance, and other magic), and hackers (disabling glyphs of warding, etc.).
• Other skills: getaway drivers, muscle, insiders, and fixers (who acquire what’s needed to get the job done).

Together these roles make up a heist crew. Most jobs require specific roles so it’s a good idea to get input from players ahead of time to ensure their character has a place in the scheme. It’s possible that a crew has worked together before, or the mastermind could bring the group together specifically for a heist. Either way, there are opportunities to create interesting dynamics between characters. Communicating with players to develop connections and backstories that work together is a great way to build these relationships early on.

The Hook

As with any adventure, a hook is crucial for setting the scene. In the case of a heist, characters need a motivation for doing the job. Is it the heist supposed to be the one that ends all jobs so the crew can retire in comfort? Are they stealing something to stick it to the man? Each character should have their own motive for joining when the mastermind comes knocking on their door. As DM, it’s your job to help players find the right hook.

The Plan

Meta gaming be damned, planning is the heart of a heist adventure. Characters should be given ample time to devise a strategy which could also include staking out the location or the mark. The crew needs to know the plan, how they will pull it off, and what potential hurdles they need to overcome. This planning can be done as a montage with DC checks along the way to obtain information before they start the job.

The Fake Out

No matter how much they plan, characters can’t account for everything. Some elements of unpredictability should be added to challenge the characters and potentially lead them off course. Maps are crucial to running a good heist and in Roll20 the ability to hide things with fog of war or in the GM’s layer is incredibly helpful in this stage of the job.

There are lots of ways to mess with expectations. One way is to hit the crew with something they hadn’t planned for. It could be a member of the group or an enemy that is a loose cannon, an unexpected guest arriving, or a change in security detail. It could even be a competing heist crew showing up to get the job done. By adding an unplanned element to the heist — something the characters can’t be quite sure how it will turn out — you create more of a thrill for the players when they’re able to pull the job off.

The Conclusion

After the plan has gone wrong and the unpredictable factor has wrought havoc on the job, you need to help the players see how their characters prevail. Ideally, they can bounce back from adversity to triumph in the end. Whether they pull off the heist or not, the conclusion needs to be equally as convincing and gripping as the rest of the adventure. By the end the characters have likely incurred some losses or came incredibly close to being caught or killed. Ultimately, they need to be able to walk away from the adventure answering the question: What was the point? Did they get what they wanted (see “The Hook” above)? Or was the heist more of a metaphor for their troubled lives? In the end, maybe the real treasure was the friends they made along the way.