Guide to creating your own heist

You have 2:30 hours to infiltrate the gala, locate the papers secured behind a well guarded door in the host’s office. You must not be seen and no casualties should occur if possible. A carriage will be waiting for you in the backyard.

Everybody likes a good heist, but it is often seen as something very difficult to accomplish in D&D. Having heard that the new adventure Waterdeep: Dragon Heist didn’t feature any actual heist, I thought I could design one myself. For these, I rewatched some of the most well known heist movies and took notes from the ones from GTA V (which are the ones I decided to take more from).

 

By TheGryph 

Time limit (optional)

Having a time limit is more of a flavor thing as most things in a heist happen almost immediately or in few minutes. However, it puts a sense of pressure in your players. Make them succeed at the last second and you’ll see how they start cheering.

Having a map (optional)

I’ve found out heists work entirely different when players know every single detail about the location than when they don’t. Do you want the PCs to investigate themselves what they are looking for by making questions and following people from afar? Or do you want them to have everything planned out from the start and know how they need to move at the location in order to avoid guards? Consider starting the heist at the beginning of the next game session to give the players time to coordinate their movements if you are to choose the latter.

You may want to give your players a flawed or incomplete map. That can also be fun, but be wary some players may not like it.

Having an inside man (optional)

This is often used in heist movies or games and adds some depth to the planning. You need to find this person before achieving what you came to do. Why is that? Is this person the only one who knows where the item to steal or target to assassinate is located? Does he/she know of a secret code you must use? Is he/she supposed to make a distraction for you to enter a building?

Another fun part about having an inside man you must locate is to find a way to escort him/her out of view from the other people who may be nearby. There are lots of ways you can use this type of concept!

 

By The Alley

Guards

What’s the fun in a heist if what you are looking for isn’t heavily guarded?

Place numerous guards in specific places to control most of the place. Try to leave at least one opening for your players to take advantage of. You can always inform the players at which time the guards start patrolling or change places to help them with their plan.

Consider having not only normal guards, but also magic users and/or dogs if the place is guarding something of utmost importance.

Locks

This is the things for rogues to shine! (or magic users if a door is magically warded or locked). Taking into account everything is located in a medieval fantasy, normally we don’t have computers to hack into. This is replaced by having intricate locking mechanisms and traps for the players to deactivate.

Reward the players for waiting for someone to get in instead of just breaking into a place by describing how that person deactivates the traps when they enter, or where they hide the key when getting out from there.

A role for every player

What I find to be the best part about heists is that everyone is given a task that must be accomplished for the plan to succeed. This mission doesn’t depend on only one guy, but all the party (and maybe some npc to fill in some role). If one is to fail everything could start getting wild.

Make sure as a DM to have each of the players fulfill a specific task, and give everyone a time to shine. Also, change the focus continuously during the heist for the players to inform you what they are doing.

Generating a distraction, getting the escape vehicle prepared, lockpicking closed doors, putting guards to sleep, having a good view of the guards’ movements and gathering information are just some of the roles your players could have. Establish this beforehand to make all this more organized. A disorganized heist can become frustrating very quickly.

Escape

The escape method will depend on how much of a ruckus you make while fulfilling your tasks. If everyone moves super stealthily and no one notices your presence, you may be able to get out from the front door. However, escaping by ship, on carriage, on a flying carpet waiting for you at the rooftops, or on a horse waiting for you outside, while being chased for being discovered can also form part of the plan. 

 

By JordanJardine

Complications

A plan can work flawlessly, but where’s the fun in that? Failing in checks will make for most of the complications you encounter. Maybe the rogue can’t get the door open. If that’s the case, the barbarian can try breaking it down which can generate a lot of noise. What if you need to throw a key from one corner of the room to the other for a party member to catch it? If it were to fall, an alarm could be triggered, and that’s where the fun and desperation begins.

Also, just like with random encounters, make a table of things that could happen every time you change focus between the player’s locations. Some examples are:

• A guard decides to go past the player’s location to get some water
• A guard forgot his weapon in another room and will go get it
• A cat shows by and starts meowing loudly
• Roomkeeping passes by the player’s location
• A person seems interested in the way you look or behave and starts a conversation
• A guest comes out from an unexpected place and notices you
• Someone decides to go for a smoke outside and walks past you

Your players may come up with strange ways to infiltrate or deal with situations. Get ready to improvise and create new complications on the spot if that was to happen.

Puzzles or secret doors (optional)

Depending on the kind of heist you planned out you can create a room with a puzzle or secret doors to avoid certain locations. This type of things can happen if you infiltrate ruins that are being guarded by cultists, or find a door that can only be opened by solving a puzzle like the one from The Pacifier movie (making a puzzle code based on a song is something that should be seen more often). Secret doors can also be seen in mansions as sewer ducts, or ventilation systems (you don’t find the latter very often in D&D though, for obvious reasons).

Communication (optional)

In heist movies the main characters are always communicated to a guy on a van waiting outside, while also being able to talk to all the other ones who infiltrated the place. If you like that sort of thing use Sending Stones or something like the Critical Role’s homebrew Earrings of Whispers for the players to stay in contact at all times. Try only giving one pair for them to split up strategically from the beginning, or not giving any of these at all, to depend on the plan they created before starting the heist.

Be generous

As always in D&D, tip the scale to your player’s side, specially during a heist, as one little mistake can collapse all their planning. Don’t force it very much though, as trying to solve a situation on the spot creatively after failing at doing something can make for some unforgettable moments. Also, reward creativeness instead of punishing your players for thinking outside the box. Doing something crazy may be more difficult to accomplish, but it’s not impossible. You want this to be memorable, so let your players enjoy the moment.

Back to planning tokens (optional)

I saw this done by Mark Hulmes in a game he ran during the Stream of Many Eyes event held by Wizards of the Coast to promote their new adventure. If you want to adjust the difficulty of the heist consider giving 2 or 3 tokens of this kind to your players. What does this mean?

Have you ever seen those scenes in movies when the characters start following a plan during the heist and the scene is cut to show the protagonists talking about how they should deal with a situation they could encounter before it happens, to then jump again to the other scene having the characters solving the problem just as they planned? 
That’s what we want to accomplish with the tokens. At any given moment during the heist, when the players deal with a situation they didn’t plan out,  they can spend one of these tokens to pause the action for a moment, and talk freely as if they predicted these situation could happen (like a flashback from the planning part). When they are ready, go back to the heist and let them try what they planned out.

I find it to be a really original idea that can help make sure the players have a higher chance to succeed. And also freeze framing scenes is awesomely fun (both for players and DM).

By Ranivius

Are you ready to run your swashbuckling heist? If you don't agree with one or more of my advices, or have some extra ones to give make sure to write them in the comments!