Dungeons & Dragons

Hits, Crits, and Fails: D&D Heists

Dungeons and Dragons

The six-person crew stood around the parchment-littered table, poring over the maps and notes from their recon. Their target: A warehouse that stood among a cluster of other brick buildings and businesses by the docks, curtained by the smell of fresh fish and salt-soaked wood.

The City Watch had the place on lockdown. They’d just busted a big smuggling operation, and in the morning, crates of nasty chemicals were going to go up in a big bonfire on the beach. It was, overall, a win for the good guys… but there was one problem.

Among the drugs were legitimate shipments, including a crate of darkwood seeds, poisonous if eaten, but otherwise harmless and very valuable.

The group was after those seeds. They were key to their benefactor’s livelihood, and if he lost them, he lost everything. He was willing to pay top dollar to a crew of rogues to rescue them, and this group was happy to accept the coin.

The watch guarded the warehouse day and night until the drugs could be destroyed, and knowing the zeal of the Watch to clean up the streets, it meant those darkwood seeds would likely be tinder in the morning. Their job was simple: get in, steal the crate, get out, leave no trace they were there. If the Watch thought a box of dreaded Demon Blood had been taken from under their noses, they would be tearing the city apart the next day. It was vital that they left no trace.

Of course that meant getting through barricaded gates, locked doors, and moving a three-foot by four-foot crate without attracting the notice of the Rangers standing guard or their animal companions perched above and constantly watching every nook and cranny.

They talked about tunneling, but didn’t have the tools to do so quietly. They talked about going in through the roof, but then there was no way to get the crate out, and the animal companions would spot them in a heartbeat.

All the while, the clock was ticking on the big bonfire tomorrow morning.

They weren’t high enough level for the flashy stuff like invisibility or teleportation, and even their best sneak wasn’t good enough to remain hidden from a dozen guards and their matching animals all getting spot checks every round. 

And then… inspiration.


I ran a thieves campaign back in the ancient days of edition 3.5. Now, a heist in D&D tends to quickly become either a fight or a chase scene depending on what the players typically do, and this is often discouraging to DM’s that really want to do a fun little heist game. How do you keep it going when they screw up? What if they all get arrested? Suppose they just try to murder their way through all the guards?

A lot of attempts to create an Ocean’s 11, Italian Job, or Leverage type of D&D game in any edition usually results in either having to railroad the players back to center, or things go so badly that the entire group winds up in prison. And while the threat of consequences adds tension, having the entire crew be arrested mid-heist tends to feel a lot like failure, which turns a lot of players away.

In a typical D&D game, while combat gets spiced up with different tactics and strategic thinking, inevitably it sort of boils down to “spam the attack button until the health bar falls off.”

But in a heist game, things are a little different, and need a lot more forethought and planning. This can be both more challenging, yet simpler. There’s no CR rating for a bank. Sure you can beef up guards as the group progresses, but the mechanics for a good heist just aren’t really built into the game as-is. Besides, ideally, the players shouldn’t even encounter the guards, and bypassing them with a good bluff is very different from taking them all on in single combat. So you sort of have to play fast and loose with the rules themselves, which I was able to do, because, well… This was 3.5, and the 3.5 rules are… complex. I didn’t have the best grasp on all of them because I’m not a human computer, and I admitted that to the group at the start. Instead I made the focus largely on roleplaying and creative thinking.

But in some ways, making a heist target was a little easier once the traditional mindset of encounter balance went out the window. When I built the warehouse, I had no idea how they were going to get in. I realized, that wasn’t my job. My job was to build the wall, and it was their job to find a way through it, or in this case, under it. Now, they could have attacked the guards, created a diversion to draw them away, or tried their luck sneaking, but the badgers… The badgers were genius.

In 3.5 celestial dire badgers have a tunneling speed and could be summoned with a spell the group had access to from their sorcerer/forger. It’s done magically, so it is utterly silent and incredibly fast.

The building across the way from the warehouse was much easier to break into. Once in the basement, the silent tunneling of the badgers brought them right across the way and into the warehouse from below. They grabbed the crate, lugged it back through the tunnel, and then had the badgers close up the tunnel behind them. A splash of mending and there was no evidence they were ever there. They were level 3, and it was one of the cleanest heists I’d ever seen. This was their first mission of an entire campaign based around thieving, and I knew right there the campaign was going to be a blast to run.

So when running a heist game, I find the best way is to change your mindset going in, and let your players know what the expectations are. This can help prevent the murder-hobo mentality and redefine what success and failure look like. 

First, go light on the rules and lighter on the combat. Sure, have the guards be tough, but only so the players are sufficiently discouraged from a frontal assault. Throw the CR system away, it’s utterly broken in the first place. For 5th, I’d recommend doing milestone XP and roll that reward in with the jobs they do. Each successful job boosts them with money, and maybe some non-mechanical benefits like making an ally, or boosting their reputation. Let their successes open doors for them to branch out into the world around them, like receiving a favor from a member of the nobility or getting sweet discounts on magic items.

Second, build a challenge that makes sense for the world. Something like a bank in a fantasy setting is going to have a lot of magical-based security, and it really allows you some interesting ways to flex your creativity. Maybe there’s a protective ward that summons a creature if someone without the right talisman opens the vault. Spill that detail ahead of time during recon and now they have to steal a talisman to break into the vault, like it’s a master key. So now one job becomes two jobs, and that increases the challenge.

Third, don’t give them an obvious window. There’s no fun cracking the safe if the key is right there in front of them. They have to earn it, and it makes opening that impenetrable vault all the sweeter. So in the prior example, they know they need to get the right talisman, but aren’t exactly sure what it is or where. So they have to do some more recon, maybe follow the bank manager home and find out it’s a ring he wears on his finger that he keeps in his safe at home. The safe is hidden behind a family portrait and the combination is his daughter’s birthday. This requires getting to know the NPC, and maybe creating an ethical dilemma, as he’s probably going to lose his job if they break in using his talisman. Maybe they’ll feel so guilty they want to find another way in. Players can be unpredictable like that, so be ready for a sudden left turn.

Or maybe they’ll try to make a fake artifact and hope it fools the vault. As I’ve said before, D&D is a game that almost encourages cheating, and there’s such a dirty little thrill in pulling off the perfect crime, the ultimate cheat. When I ran this game for my players, they were 100% into it. Every challenge I threw at them, they found inventive ways to beat the toughest security I could think of. It was a blast. Not every job was a success, but they never felt disappointed or cheated by the outcome because they earned each success. They would spend entire game sessions just on planning before even a single roll was made on the job itself.

So be adaptable, and set the right expectations. This might not work for every group, but if you think your players are up to it, there’s no reason not to give it a try. Heists are fun, and you might be surprised at the creativity of your murder-hobos if they suddenly find a different challenge before them than spamming the attack button.