“Heists don’t work in D&D!” retorted my friend and fellow Dungeon Master, when I announced I was excited to get my hands on Keys from the Golden Vault.

It’s a common refrain, usually followed by: “You should try Blades in the Dark!”

According to its many detractors Dungeons & Dragons is, in fact, a terrible system for almost every style of RPG adventure out there, from horror stories to murder mysteries, and forget any campaigns based on political or social intrigue. Hell, I’m pretty sure there are folk who will tell you that Dungeons & Dragons is rubbish for dungeon crawls. (Shadowdark, anyone?)

And, while I might not turn to 5e to play out an entire campaign based on crime and capers, if you’re already playing D&D, and simply want to bring a heist storyline or two to your table, you’ll find that 5e is a perfectly fine system for realising all your Oceans 11 and Mission Impossible-style fantasies. You may have to adapt your DM style and prepare a little differently to usual. But hey, that’s what I’m here to talk about today…

Rappelling into Revel’s End prison…

Before we talk about prepping and running tips however, let’s start by defining what makes a heist adventure a heist, and consider how these scenarios should be structured. The first half of this article should prove handy for Games Masters looking to run heists in any RPG system. In the second half, we’ll zone in on some more D&D specific advice and tips.

What is a Heist?

Simply put:

A heist adventure is one in which the players must break into a secure location, complete an objective (usually the theft of a valuable object*), and make their escape.

It is a sub-division of the classic RPG fetch quest. But, if the typical D&D fetch quest involves stumbling into a dungeon, dealing with any monsters encountered with brute force, and then groping around in the dark for the MacGuffin, a heist encourages players to research the target location first, make a detailed plan of entry, and requires the use of stealth (not force) to achieve their objectives.

For a heist to work, therefore, the combat threat at the adventure location should be far beyond what the players can handle in a fair fight, and the DM needs to communicate that. Otherwise the players may treat the heist like a typical hack’n’slash dungeon, and wade in without thinking – crashing the adventure premise and likely getting themselves killed in the process.

Careful planning and stealthy execution are hallmarks of a heist…

Another major difference between a heist and a typical D&D fetch quest, is that in a heist the players usually know the precise location of the MacGuffin before they enter the ‘dungeon’, and have at least an inkling of what traps and security lie in their path; whereas a fetch quest comes with the expectation of having to conduct a room-by-room crawl to locate the item, dealing with any obstacles as they come up on a more improvisational basis.

Now, GMs can decide whether gaining this advance knowledge (the MacGuffin’s exact location etc.) forms part of the adventure (see Intel Gathering below) or whether an NPC or quest-giver supplies it, but using this knowledge to plan the raid is an integral part of the genre.

(*While the objective of a heist is usually the theft of an item, it might also be rescuing a prisoner, or delivering a message. In other words, the crux of a heist centres around stealthily infiltrating a secure location).

Ok, now we understand what a heist is, let’s go deeper…

The 6 Stages of a Heist

I’ve read various blogs, and watched various videos, that break heists down into three or four stages: but I would say there are actually 6 distinct parts to a heist, even if one or two might not be apparent in the running of every single caper. (You could also make a case for 2, 3 and 4 being a wider Planning and Preparations stage, but I think understanding the distinctions between them is useful for GMs).

1. Assembling the Team

A classic part of the TV and film heist genre (think Sexy Beast, Reservoir Dogs, Oceans 11 or Casa de Papel), this stage is great for building excitement as the ‘brain’ of the operation pulls together a crack team of specialists required for the job. This stage will rarely play out extensively on the D&D table, as the party usually are the team, and the first scene normally features them already assembled by the quest giver… but occasionally you might have a smaller adventuring party go out and recruit an expert NPC or two to help with a job (give them a choice of NPCs to work with if so, some more trustworthy than others, or have them make Investigation checks to get someone who is any good to help out!).

2. Intel. Gathering

Sometimes the quest giver will provide a handy info dump for the party on the heist location’s security measures, including guard rotations, alarm systems, traps etc., effectively completing this stage of the job for them. That’s a handy headstart if you’re running a one shot, but, to fully evoke the heist experience, and if time allows, consider pushing the players into performing their own reconnaissance. Casing the joint, stake outs, shake downs of former employees, and other channels of research and investigation can all contribute to a true crime caper vibe.

3. Planning

Armed with what they learnt in stage 2, now is the time for the players to meet in a smoky basement, put their heads together, and plan their assault on the location. How will they get in? How will they disarm the security around the MacGuffin? And how will they get out? During this stage, they may realise they need some specific equipment, or that they need to perform additional preparations…

4. Preparations

Depending on their plan, the party may have to go shopping, prepare disguises, forge a document or two, bribe a guard, plant a crew member in the location, perform a dry run of the mission, or practice their parkour, before they can pull off their heist.

5. Execution

It’s all systems go! The players must execute their plan, infiltrate the location and hone in on the target, overcoming any final layers of security to get their hands on the elusive MacGuffin.

6. The Getaway

With the target now in their possession, the players must exit the location and then flee a safe distance, losing any pursuers in the process. If they succeed in making the final rendez-vous with the rest of their team, then it’s cava and caviar all around… after all there’s no way Dave has jetted off to Rio with all the diamonds by himself. I’m sure he’s just caught in traffic…

Designing a Heist Adventure

One of the best things about running heists is that they are very formulaic, and once you’ve mastered the formula you’ll be able to run any number of successful capers, just changing up the adventure’s core elements, and adding twists or a touch of the unexpected to keep players on their toes.

All heist scenarios share the same 3 core elements, which are:

1. The Target (aka ‘MacGuffin / The Score’)
2. The Location (aka ‘Fortress’)
3. The Security 

And then you have an optional 4th element, namely:

4. Complications

Let’s take a look at each of these elements, and what DMs need to consider when designing them.

1. The Target

Often referred to as the MacGuffin, obtaining the target is the mission’s objective. If the target is loot, it might also be referred to as ‘the score’.

To really evoke the heist vibe, the target of the caper should be something truly wondrous or valuable. The target’s high value is what justifies the high security, which in turn demands the advanced level of planning required to pull off the job. This is no ordinary burglary, so a good heist needs a more memorable target than 50 gold pieces in the family safe.

In Keys from the Vault, interesting targets includes an eldritch egg, a sentient painting, the still-beating heart of a king, and the Book of Vile Darkness itself, while more than one heist requires the obtaining of information, like persuading a prisoner to part with the names of three powerful devils. From the world of TV and film, information is a classic target: the plans of the Death Star being an obvious example.

Worth its weight in dirt…

2. The Location

While a memorable target is a boon, more often or not the target is a MacGuffin in the true sense of the word, i.e. a plot device required to make the adventure happen. The heist location is the true star of the show, and just the mention of it should get the players excited for what’s to come. The Keys from the Golden Vault does a great job in this respect by treating us to some unforgettable locales, like an efreeti’s fortress, a Feywild palace, a svirfneblin mining town in the Underdark and a bedevilled music conservatory. (Obviously, none of those are quite as cool as a Bloodwizer-sponsored airship replete with Skybubble hot tubs, so head over to the DMs Guild if you think your players are capable of pulling off an Incredible Balloon Bamboozle!).

Of course, classic heist locations, like banks, can be fun as well, but be sure to give them a twist! Keys from the Golden Vault did a nice job here too, with a Nine Hells-themed casino in an underground cavern, a panopticon prison in a frozen wasteland and an interplanar train cruising through the skies on its way to Mechanus.

An interplanar train makes for a great heist location in The Concordant Express

Aside from cool factor, what any good heist location needs – in terms of gameplay design – is a few different ways to get in. For players to feel like they are criminal masterminds, they need to be able to consider the pros and cons of different options, not feel railroaded towards one specific way in. Meanwhile, none of the ways in should be easy, rather each should be challenging in different ways. The front door has the most muscle guarding it, but could be infiltrated by deception. The back door is lightly guarded, but further away from the vault, with an inner door that is magically locked. The chimney is unguarded, but presents its own dangers (getting stuck etc.), and leads straight into the duke’s bedroom.

Thinking about how the location receives messengers, visitors and supplies, and how it disposes of waste, could provide alternative ways in for the players who do a good job in the Intel. Gathering stage of the heist (see above).

The Vault. A subsection of the Location is ‘the Vault’, the final impenetrable room with the toughest security measures. This could be a classic booby-trapped safe, but here’s another chance to put a twist on proceedings with something new and original…. maybe the vault is a glass coffin submerged in a pool of acid?

3. Security Measures

Once you’ve mapped out your location (and you need to do this in some detail, as clever players will want to know the precise whereabouts of every skylight, cat flap and crap chute), you need to flesh out the security measures in place.

As mentioned, you can divide these into a) Guards and b) Obstacles.

– Guards

You want your guards to be the focus of your location’s security measures: and to create a truly immersive heist scenario, for your players to interact with, you need to do better than simply note down that the front gate has four guards. You need to know how many guards are at any given sublocation both by day and night, when guard rotations take place, which areas are patrolled (guards are expensive, so they can’t be placed at every key juncture) and how often, as well as where off-duty guards can be found, in case the alarm is raised.

Sentinels such as golems, that don’t require food, sleep, air or water, can be keyed into the location just as with a dungeon, but generally speaking you want to avoid the ‘encounters waiting in stasis’ style of adventure design for heists, because we want to give the location a credible working ecology – and in doing so offer the players full autonomy on how and when they conduct the caper.

Creating a credible ecology might mean planning the time of day when the giant crocodiles are fed, which in turn gives the players opportunities they can take advantage of… croc feeding time could be the ideal time to swim across the usually deadly moat, for example.

Sneaking up on unsuspecting guards in Vidorant’s Vault

Tip: One huge advantage of running heists in a fantasy setting is that you needn’t restrict yourself to liveried hobos with halberds as guards, and you might want to add in gazers (excellent look outs!), basilisks, bugbears, minotaurs, dragons or whatever else takes your fancy… just come up with a viable reason for them to be there, so your location remains credible.

– Obstacles

Obstacles include locks, alarms, arcane versions of security cameras, traps, puzzles (potentially), Entrapment-style laser beam sensors, and any other non-sentient thing that stands in the way of the party and their prize. There are some specific spells in Dungeons & Dragons lore that you might consider employing, which I’ll go over later, that can do some of the heavy lifting for you (In a lore consistent world, experienced players might even be expecting to encounter many of these spells! DMs will also need to consider security counter measures against certain spells, like teleportation, passwall, gaseous form etc. More on that point further into the article).

– Perimeter, Interior and Vault

Instead of dividing security into ‘guards’ and ‘obstacles’, another useful way to think about security is geographically: into Perimeter Security, Interior Security, and Vault Security.

Navigating each layer should have a slightly different vibe.

The perimeter security consists primarily of locks and ‘eyes’ (guards and/or cameras), and presents a formidable challenge. Fail here and the adventurers could bring the mission to an abrupt close, or possibly put the location on high alert, making their work significantly harder from then on in. However, if the players performed the preparatory stages of the mission properly, they should be well placed to infiltrate this initial layer.

Interior security is typically the weakest layer of security, as intruders are not expected to make it past the perimeter – the interior of the ‘fortress’ might just be denizens of a castle going about their business for example. Defeating interior security usually means ducking into doorways and / or pretending to be fetching a sandwich from the kitchens for the Duke, but you might consider some roving guard patrols and potentially a trap / alarm or two, if no one is supposed to be there (like a museum or bank after dark). While less formidable than perimeter security, players often don’t know what to expect from interior security, so you can play on their ignorance to create tension, or perhaps throw them a curved ball. Usually the castle is deserted by night, but tonight of all nights, the Duke has stayed up late to celebrate his birthday… the castle is awash with drunken guests swaying through the corridors!

The final layer of security is the vault security, and this should, of course, be the toughest to tackle. Elaborate combination locks, exploding runes, forcecage traps and final guardians all find their place here. Ideally the players’ intel. gathering means they should be at least semi-prepared for what awaits, in order to give them a fighting chance.

A waterlogged vault in Casa del Papel makes for a great final challenge…

Setting the difficulty level: When designing a heist, DMs need to strike a balance between creating a credibly secure location (i.e. a mage’s tower is going to have alarm and glyphs of warding etc., wards against teleportation and clairvoyance, and likely some see invisibility devices) with an appropriate difficulty level. If the location is totally impenetrable, your players are going to fail no matter what and have a miserable time. One way to make breaking into an impenetrable fortress possible is to build in (believable) weaknesses to the security that the players can discover in the Intel Gathering stage. Once a month half of the guards are obliged to leave to celebrate the birth of their God; budget cuts mean there is now only one sentry per tower and the traps haven’t been serviced for months; the mage responsible for casting alarm (8 hrs duration) does so at 9pm, meaning there’s a period after 5am when all the alarm spells are down, and there’s only a handful of night guards on duty. Or, if you really do want to create the ultimate ‘fortress’, dangle it front of your players like a prize for when they reach higher levels. Sure, let them attempt it now, if they dare… but at least you’ve warned them!

4. Complications

Heists rarely go smoothly! Part of the fun of any caper is the would-be burglars having to think on their feet to overcome the unexpected complications that threaten their operation. In the introductory chapter of Keys from the Golden Vault, suggested complications include two classic devices: the moving MacGuffin (the players crack the vault to find it empty… as per Honor Amongst Thieves!), and the rival crew… a second bunch of thieves who try to swoop in ahead of the party, or otherwise make their lives difficult.

One of my favourite complications from the actual KftGV adventures takes place in The Murkmire Malevolence, as the object of the heist is in fact the egg of an eldritch horror ready to hatch at any given moment. Generally speaking, any unexpected obstacle, or discrepancy between the party’s intel. and the reality of the situation, can be considered a complication.

Being frank, while they’re great in the movies, complications aren’t always necessary, or recommended, when running a heist in D&D… the swinginess of the dice and the chances of the players fucking up several of the many skills checks that stand between them and their goal are going to create plenty of organic complications, without the DM having to artificially insert more. BUT it’s worth having a couple up your sleeve, just in case things are going rather too smoothly for the party and you need to spice things up. If you are able to deploy them, without totally sh*tting on the players chances of pulling off the job, complications are certainly a lot of fun, and tend to elicit those rueful groans from the players that every DM loves to hear.

Social Heists

During his video review of Keys from the Golden Vault, Eric ‘Rogue’ Watson divided the heist locations into hostile and non-hostile environments: meaning some locations, like the efreeti fortress of Brimstone Hold and the automaton-ridden village of Tockworth had a kill on sight policy towards intruders, while other locations like the Afterlife Casino and Paliset Hall have an open door policy (at least for folks going about their legal business, or those with a party invitation).

I thought that was an interesting observation. Obviously every location becomes hostile once the players’ larcenous intentions become apparent, but a certain type of heist adventure design allows players to get closer to the target, usually by attending events taking place in the target’s location. The opening gala at the Varkenbluff Museum is a great example (from The Murkmire Malevolence), as is the Three Dragon ante tournament at the Afterlife Casino (The Stygian Gambit), and the Sky Party on the Dragonbowl Airship (The Incredible Balloon Bamboozle). In each case, these events allow players to get closer to their goals by openly appearing in person, albeit often in disguise. These are what Eric Watson would call heist adventures featuring non-hostile locations, but I prefer to label them social heists.

Social heists are really fun because they put players in a position where they have to interact with NPCs, use deception and think on their feet, as well as use some underused D&D abilities and spells. You can make almost any heist a social heist, by including an event in the heist location… for example Fire and Darkness could become a social heist, if the efreeti boss decided to throw a feast to celebrate a recent victory on the battlefield.

Another name for these would be Front Door Heists, as, instead of rappelling through a skylight, one simply waltzes in through the location’s main entrance (and then waits for the right opportunity to sneak off into the shadows to find the safe). When you plan a social heist you are effectively substituting Stealth and Athletics checks to get past the perimeter, for Deception and disguise kit checks to convince the relevant NPCs you’re supposed to be in the interior.

The Incredible Balloon Bamboozle

Ok enough with the artfully woven-in adventure plugs, here’s the slap-in-the-face promo spiel for my own recently released heist scenario… The Incredible Balloon Bamboozle. Inspired by the Keys from the Golden Vault, I revised the Airship Heist side quest from my 5-star best selling DRAGONBOWL adventure and developed it into a standalone adventure.

Recognising the fun potential of the social heist, for The Incredible Balloon Bamboozle I deliberately leaned heavily into this style of caper, setting up a scenario in which the players must impersonate various NPCs to gain access to a VIP party. The adventure tests each player’s improvisational skills (in what are designed to be hilarious ways!), as they maintain their cover while on board the Dragonbowl Airship, while presenting them various options to infiltrate the blimp’s upper sections (where the dirigible’s technical blueprints are safely stored).

The adventure ends with a complication to end all complications, as Xanathar itself leads an aerial assault on the airship and attempts to blow the blimp out of the skies.

>>> CHECK OUT THE INCREDIBLE BALLOON BAMBOOZLE <<<

Players must plan their assault on the airship’s Head Office…

Running Tips

So now that you know what a heist is, you are able to distinguish the 6 different stages of gameplay that will play out (just signposting these stages, either directly, or through an NPC, goes a long way to creating the desired vibe!), and you understand how to design a heist adventure, you are more or less ready to summon your fellow dice rollers to the table!

But before you send that Whatsapp message, let’s just run through a few more tips on running a successful RPG caper…

i. Dealing With Failed Checks

Perhaps the one thing that could ruin your running of a D&D heist is using an unforgiving interpretation of the rules for skills checks. In any given heist, the adventurers are going to make a LOT of skills checks, and what we really want to avoid is for the game to implode on a single bad roll – whether that being the first PC to attempt to sneak past the guards, or the only rogue in the party fumbling the all important thieves tools check to pick the vault’s lock.

Bad rolls are going to happen. Most likely they are going to happen often. So if you build a scenario where the party have to individually succeed on even three or four crucial rolls to pull off the heist, then they will fail.

On the other hand, if you repeatedly allow players who fail at skills check to simply try again, the game world loses any sense of reality and consequences. The players will feel they are playing the adventure on cheat mode. And, even if they complete the heist, they won’t get any great sense of satisfaction from having done so.

There are actually a few tricks and techniques we can employ here to prevent failed skill checks derailing the adventure.

Failing Forward. Failing forward is a much-fêted technique that every good Dungeon Master should have in their refereeing repertoire. As the name suggests, the players may fail a roll, but the adventure still moves forward. It works by allowing the players to succeed on a skills check they failed, but at a cost, or with an ensuing complication. When the rogue rolls a 2 on the dice, it doesn’t mean the lock is beyond their abilities to pick, it means their lock pick broke in the process, or they injured their hand, or they made a loud noise in doing so. In other words they failed to do a good job, rather than failed outright, and the story continues…

Failing Sideways. Ok, I made this term up, but another way of dealing with a failed skills check is to enforce the failure – the door is still locked – but to give the player another go at the challenge. But you just said failure should have consequences? And it should. To acknowledge the failed roll, you can now raise the DC of any subsequent checks, or stress that each failed attempt costs a significant amount of time (obviously this only really works if they are labouring against a ticking clock!). You can also enforce the same type of complications I mentioned in Failing Forward, but this time they haven’t achieved their objective and still have to come up with a good roll to progress. I like Failing Sideways, because it’s a bit grittier than Failing Forwards, which is cool and cinematic but feels a little bit too generous at times.

Accumulated Failures Needed to Fail. One of the reasons Blades in the Dark is hailed for its heist-enabled gameplay is its progress clocks mechanic. Progress clocks measure the success of a task over a number of rolls, with final success dictated by achieving X amount of successes before Y amount of failures. This helps mitigate the role of luck, tipping the probability balance of success firmly in the players favour (assuming they are any good at the skills they are attempting!).

This is a bit similar to how group checks officially work in D&D, in that a group check is considered to have succeeded as long as more players succeed than fail (I actually have a house rule for group skills checks that I prefer, if you wish to check it out). But progress clocks offer more flexibility than standard 5e group checks (you can make tasks easier or harder by changing the number of successes needed vs. failures), and they can also be applied to solo endeavours, or applied to a complex task. A sophisticated lock, for example, might require 5 successes before 3 failures to pick, which could also be spun out into a dramatic mini-scene.

An advantage of this system is that players can also see when they are doing badly, and perhaps throw some extra resources (different forms of inspiration, guidance etc.) at the problem, or change their approach to the situation.

Use the Suspicion Mechanic. If you bought Keys from the Golden Vault, turn to page 60 to read about the Suspicion Mechanic introduced in the Prisoner 13 adventure. Essentially, the more suspicious shit that goes down, the more alert the guards become and the harder they are to sneak by or deceive. This gives DMs a nice consequence they can apply to failed Stealth checks etc., without having to immediately bring the house down on them on a single botched roll.

Stacking the Odds. I’ve blogged before that DC 15 shouldn’t be 5th edition’s go-to DC. It seems fine when it’s a Perception check thrown at the whole party and only one PC has to pass, but as soon as players have to individually succeed on multiple tasks heroes quickly become clowns at this difficulty class. The chance of any given character passing three different DC 15 skills checks is usually much less than 50%, and will often be less than 10%. My advice, keep the DCs as low as possible and award advantage as readily as you can, without appearing to go easy on the party. “The wall is DC 10 to climb, but with your grappling hooks and rope you get advantage.” And while I generally hate rerolls (they undermine the whole point of rolling dice in the first place), I can stomach the characters starting any given heist with 5e’s single point of inspiration. I do also approve of story-earned re-rolls. Maybe have the party’s patron suggest they leave an offering at the Temple of the God of Trickery before attempting their endeavour. If they succeed on a Charisma-based Religion check, while doing so, they get one or more ‘luck‘ points which they can use during the heist.

Success Can Go A Long Way. If a character succeeds on a Stealth check, in particular, let them carry that result forward as far as possible, before calling for another one. If players need to succeed on a new Stealth check every single time they pass a guard, it’s inevitable they are going to raise the alarm sooner or later and you’ve essentially given them a 100% chance of failure. If, however, they roll a 15 to get past the first guard, let them keep going further into the fortress until you feel a higher roll would be required to progress, and only then say… “you peep into the courtyard and see four guards practicing their swordplay. If you want to sneak through here, you’re going to need to pass on a new DC 20 check.”

ii. Planning For Failure

Some DMs feel that for D&D to be fun the players have to succeed, and what is decided at the table is not whether they succeed, but how they do so. I am not one of those DMs.

For success to be meaningful, failure has to be possible. And one of the great things about heists is that players can fail and the session can continue. Guards rarely summarily execute thieves, so if the players get caught while executing the heist simply have a plan for what the guards do with them. Maybe they bring them before their boss for questioning right away, but most likely they will lock them in some kind of cell (which, for gameplay purposes, needn’t be particularly secure). Depending on the scenario, the thief might get away with being escorted off the premises, perhaps with a mild beating and/or confiscation of some or all of their equipment.

One scenario that you almost want to play out, is ONE of the players being caught. Now you have a cool complication, but the heist is very much still on, as the party have to raid the vault and rescue their bumbling colleague.

Bond suffers a minor complication in Live & Let Die

Strokes of Luck. In general, you want to use your foresight to predict a few likely moments of failure and what might happen to keep the story moving… one device you can use are Strokes of Luck, which are essentially the exact opposite of Complications (and maybe more useful to the DM!). Nowhere are the vicissitudes of fortune more present than in a good heist, and the prepared DM will be able to inject a slice of hope where once despair reigned. Maybe, just as the players horribly fail their Athletics check to scale the high walls of the fortress a servant materialises out of a hidden door at the base of the ramparts to chuck out the rubbish. Perhaps, as the players despondently sit outside the vault, having dogfastly (I could have sworn that was a word… it is now!) refused to make a single good thieves tool check, the Duke comes whistling down the corridor to deposit a family heirloom back in the box. You can keep Strokes of Luck as a story device left to the DM’s discretion, or you can give the party one nebulous SoL at the start of the adventure to be employed when they most need it…

iii. Do Split the Party

During the running of a heist, GMs should consider it a boon if the party decide to split up, hopefully to each take care of a key task commensurate with their skills. Now you can narrate the action in cinematic style, cutting like a slick director between this crack team of specialists to focus on each person’s role in the caper.

You can even leave cliffhangers and complications dangling before cutting to the next player. “Ok, Ashara you insert your lock pick and quickly realise this ain’t no ordinary lock. You take a deep breath and concentrate, delicately twisting the pick against the lock’s mechanisms. Roll your thieves tool check… 17. You hear a loud, maybe too loud, click…. but it’s back to your turn Leif. The guard on the bridge looks you up and down, but seems to have bought your story. Where are your papers? He says routinely.”

Splitting the party also means that, if the alarm is raised, it might only be one burglar who is busted by security, and we’re back to the cool complication we planned for earlier in this article.

iv. Use an NPC Sounding Board

During the planning stage of the heist, the players are inevitably going to dream up some absolutely ludicrous shit that would never work. Obviously, your first response to this nonsense is to do nothing and hope the other players around the table point out the evident pitfalls in their plan. But it is worth having an NPC in the room too, as a sounding board. Possibly the quest giver themselves, or some other patron or ally, with some standing. You can use this NPC, not only as your mouthpiece for shooting down preposterous proposals, but also for raising important issues they are forgetting. Like how they are going to transport the 50 sacks of gold from the vault, back to their base.

While crucial to the heist vibe, you don’t want the planning stage of the adventure to go on too long (I’d suggest 20 minutes max!), or for indecision to reign, so having that NPC in the room can really expedite matters, and is a way more immersive way of ensuring the players start on track than you the DM directly addressing the players with doubts about their plan / sanity.

D&D Specific Problems

Most of the aforementioned advice should apply to running heists in any given RPG system, but now let’s look at a few D&D specific tips.

Naturally, given that it wasn’t designed specifically for the task, a wise DM considers some of the problems that D&D poses to the smooth running of a crime caper, and prepares for them.

i. Make Lowly Guards Lowly

Film heists are full of heroes karate chopping guards unconscious, shooting them square in the throat with a crossbow bolt or knocking two heads together to instantly put a pair of lookouts in la la land. D&D doesn’t really support a reliable killer or knock out blow mechanic, so if you want the PCs to be able to take out a guard before they sound the alarm be sure to give said guards as few hit points as possible. Punching a veteran with 58 hit points isn’t going to do much, so better to give the average sentinel a guard stat block, especially if they are just a look out. Similarly, during the escape phase, it will be more fun if the players can take out some of their pursuers with a single attack roll.

ii. Preparing For Magic

Magic can be both a boon and a potential issue when running heists in D&D. On the positive side, you can use magic to replicate many of the real world technologies that feature in some many of our favourite heist movies, such as Oceans 11, The Italian Job and so many scenarios from the Bond films franchise. The alarm spell takes the place of electronic alarms, arcane eyes act as security cameras, arcane lock is a complex combination lock etc. etc. You can also invent new magic spells / items to replicate anything you think is missing, or create more specific effects and security systems.

Meanwhile, you want your players to be able to counter these arcane security measures and so you want them to be able to cast detect magic to find alarm spells or glyphs of warding, and dispel magic to disable of them. Similarly, knock is a the equivalent of a stick of dynamite, and passwall is a drilling machine. These are cool tools for the players to employ, so let them! Just try to design a scenario with enough obstacles that they can’t turn the heist into a cakewalk by simply expending one or two spell slots.

Probably the most problematic magic that DMs need to be aware of is teleportation magic. Being able to jump directly into the vault, grab the MacGuffin and teleport out again isn’t going to make for a great session. Dimension Door is the lowest teleportation spell that might realistically enable players to circumvent the entire location’s security measures, and it’s only a 4th level spell – which means an 8th level wizard could use it to get both in and out of the vault. Luckily the fix is easy enough: have the location, or the vault at least, be protected by a teleportation ward. (Tip: read up on Mordenkainen’s private sanctum, as it does that and more).

Other magic that can compromise a heist is the wild shape feature, and you can expect druids to transform into things like spiders and fleas to gain entry into the vault. Given that they could then revert to humanoid form, grab the MacGuffin, and use the wild shape feature again (I believe its two uses between short rests, even at low levels) to get out, this could be a problem. The best solution is probably to design a vault with sufficient obstacles that the druid can’t go it alone once there, but you could also consider airtight seals, or even place a few hungry geckos in your ‘dungeon’ to eat up any burglar bugs. Similarly, a few house cats can prevent familiars from wondering around the target location with impunity.

Dungeon Masters might as well refresh themselves on some of the more common information gathering spells that we considered in our post about running mystery adventures. However, in heists we typically want the players to be able to gather plenty of information. What is vital is that getting into the vault remains a challenge… which reminds me, players are likely to make use of the spell pass without trace if they can. This spell has always felt spammy to me (plus it reads like you should only be able to cast it in dim light). But in any case, not even a roll of 30 on a Stealth check allows you to pass right in front of a guard’s nose, and you could always employ those Entrapment-style lasers if you want the party to work a little harder.

iii. Something For The Whole Party

Most D&D classes have some skills that can be used to good affect in a heist scenario, besides which performing a successful heist depends on as much the wits and decision making of the player behind the character, as the character’s own stats, skills and spells. Clerics, fighters and barbarians are perhaps the least ‘heisty’ of the D&D classes, but if you build in some Athletics challenges, or other checks tailored to their specific skills you should be able to keep them involved. You might consider being more relaxed with the rules that usual… maybe you could allow bless to affect skills checks instead of attack rolls, or rule that a high enough Athletics roll or unarmed fighting attack roll could knock a guard out cold (despite the fact they’re a veteran!). In general, in D&D there are always sessions where one class’s unique skills come to the fore, so it’s not a crime (pun intended) to have a session in which rogues are the stars of the show.

iv. Consider New Chase Mechanics…

During the escape phase of the heist, a chase is likely to ensue between players and guards. D&D mechanics don’t deal with such scenes very well. I’ve proposed some rules that have helped me improvise better chases in the past, and I might simplify them even further for you now. Give each group of guards a passive ‘speed’ of 10 + their Str / Dex and then each round let players roll their choice of Athletics or Acrobatics to try to put distance between them and the guards. Succeed by 5 and they put one ‘gap’ (roughly 30 feet) between themselves and the guards, fail by 5 and the guards gain one gap on them (each player can use a D6 to measure the number of gaps between them and the guards… if they start 60 feet away and succeed in the first round, have the player turn 2 to 3 on the die. Let them know how many gaps they need to open up to escape).

To make things more fun, you can let both sides use a bonus action (during a chase, it is assumed that each creature involved uses their action to ‘Dash’) to make an attack roll at disadvantage. Mechanically, this means lots of guards missing the fleeing thieves with crossbows, which will evoke that epic action movie vibe, while the players’ superior to hit bonuses should let them still pick off a guard or two, even with disadvantage, as they run away. (Note: you may have to switch to active ‘speed’, ie. Athletic, rolls for the guards at some point, to inject more drama – especially if there are multiple groups of guards, but passive scores makes things cleaner to run!).

For shorter chases, down a corridor for example, just run a one-off Athletics / Acrobatics contest. If the players succeed they get to the door (or whatever) and can close it before the guards have a chance to attack. If they fail, the guards get to attempt an attack or grapple.

Remember, as well, to narrate the dice rolls during any chase scene… or encourage the players to. If they roll well, let them describe how they successfully put distance between them and their pursuers. You can also throw in additional checks, to avoid specific obstacles or to make heroic jumps etc.

More Heist Advice

Ok, that’s about all I have on heists for now… if you like this advice do consider picking up a copy of The Incredible Balloon Bamboozle to see some of these design points in action.

I’ll leave you with a solid article from Sly Flourish who tackles this topic succinctly on his blog.

I’d also appreciate hearing any readers tips, and experiences, in the comments.

More D&D Advice

As mentioned, I’ve also tackled running mystery stories and horror adventures on the blog previously, as well as a host of other fun topics…

How To Run (Murder) Mystery Adventures in D&D

7 Haunting Horror Stories for Halloween

Designing Unforgettable Combat Encounters for 5e D&D

Keys from the Golden Vault: Reviews of All 13 Heists!