I think it's pretty well known that the best heists are those where the party gathers information, makes plans, gets their gear together, and then in the middle of executing the plan something happens to force them to improvise and change what they're doing on the fly. It's that difference between the careful planning and the execution, in my opinion, that makes heists so fun to play and run.

In the heist I'm running for my players right now, I set up the location of the heist to be full of little surprises that would hopefully require them to improvise a little. Unfortunately, I set it up so that they'd have to improvise if they didn't get a series of improbably good rolls, as a party... and then they did just that.

(A location was guarded that they thought was unguarded... but they bypassed it simply by the dice saying they were sufficiently sneaky, and continued the plan as normal).

Now, I'm not going to take that away from them. And sometimes, it's awesome when something just goes your way 100%... but I can't help but feel that they've been cheated out of some of the fun by being too successful. Is there any advice to "stir the pot," so to speak, without being unfair or stealing their victories away from them? Basically, how can I introduce a fun twist that doesn't require a fumble of some sort from the characters?

I'd prefer answers to be system and setting agnostic-- I'm not just looking for answers about this heist, but heists in general. That said, I'm using D&D 4e. The players are seeking to empty the vault of an evil and powerful politician in a kingdom where money directly equals political power-- denying him access to the money is technically more important than obtaining it themselves, but they'd certainly like to get their hands on the money anyway (and unbeknownst to them, the vault also contains some nice plot hooks for the next part of the story). The vault is located beyond a portal in the center of the guy's main stronghold, and the portal leads to the Elemental Plane of Fire. The planning sequence involved personally scouting the outer portions of the stronghold and recruiting a pair of NPC cat burglars who previously reached the vault (but they failed to endure the plane of fire's heat and had to bail), and who unfortunately had no knowledge of changes to what areas were to be heavily guarded after their attempt.

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    \$\begingroup\$ I don't think this is system agnostic. There are systems which address this issue, there are also diceless systems, etc. \$\endgroup\$
    – enkryptor
    Commented Jan 31, 2022 at 9:11
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    \$\begingroup\$ Could you specify what system you're using to run this scenario? Although you want answers about heists in general, we want to focus on your problem, which means being aware of the constraints and expectations your system has, and the tools it has available that we can suggest you use. The way this gets addressed in Fate is completely different to how it gets addressed in Leverage or Gumshoe. In light of not specifying a system, answers will still assume these—usually from whatever games the authors are most exposed to. I'm voting to close so we can know this rather than have it withheld. \$\endgroup\$ Commented Jan 31, 2022 at 10:57
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    \$\begingroup\$ See also: Should I use a narrow system tag, or use a broader tag? \$\endgroup\$ Commented Jan 31, 2022 at 11:02
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    \$\begingroup\$ Are you players thrilled that their careful planning and execution went according to plan? Or are they losing interest and is the session feeling dull? \$\endgroup\$
    – yesennes
    Commented Jan 31, 2022 at 19:20
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    \$\begingroup\$ Just gotta say I hugely disagree with your opening premise that things going wrong is the most fun. Don't screw players over just because you enjoy failure. \$\endgroup\$
    – SeriousBri
    Commented Mar 10, 2022 at 20:00

8 Answers 8


Inflict half damage on a miss.

So an introductory word: on one level, you're fine. You presented something the players didn't expect, hopefully by actually saying something like "wait, this corridor wasn't supposed to be patrolled today" rather than just describing a patrolled corridor and trusting the players would look at their own notes and create their own surprise. As long as your players were worried while the dice were tumbling and relieved when they landed high, that little interlude has had its desired effect.

But, I get it. This was supposed to be the frostro bostro dragon, you had it all set up just that one clean hit from its bostro frostro breath would get somebody trapped in ice and things would get all dramatic, but you didn't roll high enough to hit ANYBODY, not even your clank-clank cleric. And when it got its breath weapon back again and raked everybody with it again, you somehow managed to skunk all the rolls AGAIN. It doesn't matter what kind of effort you put into describing the pulsing ice veins on its neck and the way the breath snaps and cracks in the air as it rushes past, the actual effect of the fight was just a big white dragon, not at all the experience you wanted.

You don't totally dodge a white dragon's breath, though, right? When it misses it does half damage. The type and amount of that damage (and, yes, the shape of the breath) is one important way in which a dragon of one color is different from another, and so dragon fights don't feel the same even if your players propitiate the unholy demons of DM dice jinxing. You need a "half damage" for this effect, too.

In the frostro bostro case it's, I dunno, on a miss portions of the ice cage still form all around you, creating difficult terrain in a close burst 1. Somebody can still burn a ground slam or fire wave to clear out a chunk of it and get everybody moving, and it pays off your description while still giving your players a sense they dodged something significant.

So what is it in the stealthily heistily case?

...as long as you have more than one hit point.

In the degenerate case, a stealth operation has exactly one stealth hit point. The party is either unseen and undetected, or everyone knows where they are and is closing in to capture them, with little practical room in between.

Whatever system you run a heist in, make sure it's not limited to the degenerate case, and instead offers something like a suspicion pool or a stealth clock or some sort of system-relevant way to create room between full alert and condition green. Even if the dice get you through a patrolled corridor without being seen, it's still quite a bit slower than just walking through the corridor and only having to worry about making enough noise to tip off people in adjoining rooms. And the longer you stay in...

The bank? I'ma call it the bank, you'll see why later.

The longer you stay in the bank, the more trace of yourself you can't help but leave. Lose one stealth hit point.

Or if you're in a system like Blades in the Dark where the GM can make up whatever clocks they want at any time, the time clock ticks forward or perhaps starts spinning if your scoundrels haven't previously encountered undue delay.

Of course there's the chance that you're already accounting for this, too, and the dice roll that got your PCs past the obstacle was so good they got some critical benefit out of it, such as not taking a bunch of extra time.

In the 4E case, where I'm assuming you're using some kind of skill challenge framework to set this up, your stealth hit points are your challenge failures, but the way the system is set up it doesn't make a sense to say "eat a failure even when you succeed". A simple way to pay this forward is to make whatever the next thing is in sequence one step harder, or with some kind of circumstance penalty, representing the extra effort you need to put in to make up for the lost time.

But in the broader analogy space, hit points can also be recovered and effects can be dispelled -- as long as something's possible as a result of the dice it can happen. So suppose this is one of those cases of extreme good luck and any "damage" you might have done, any clocks you might have ticked, have been preempted by the sheer flair of it all.

You can still have this leave an impact. How?

Everything happens for a reason.

That is, every effect has a cause. This corridor wasn't supposed to have anybody in it, and yet, it does. Why is that? If the cause extends beyond simply this room, then even if this room had no immediate mechanical drawback it still serves as foreshadowing for something the players might face in the future. When you call back to it later on, it will feel impactful and important even if the dice just slipped right by.

Maybe the corridor isn't supposed to have anybody in it today, because it was going to be cleaned. But Viscount Poncingjay threw a real rager last night and he's bought out every cleaning service he can find to get the place back in shape before Mumsy comes back from vacation. This could just be a fun conversation to overhear, or it could really throw a wrench in the players' plans if they were, say, planning to disguise themselves as cleaners and sneak out later.

Maybe the corridor isn't supposed to have anybody in it for the next fifteen minutes, because that's how patrols usually run. But somehow a cat got loose in the bank and it was kind of an all-hands scramble to get the darn thing corralled before it tripped some of the passive defenses and created a real hassle for security to stand down and some very bad PR. This could just be a fun conversation to overhear, or it could really throw a wrench in the players' plans if they were, say, planning to make use of precise patrol timing and now everything's been thrown off by some random time interval.

Or maybe there's a big twist you're planning from the start. The corridor isn't supposed to have anybody in it because it's a sparsely monitored overflow zone, but now it's full of a mix of regular bank personnel and security staff from the West Metropole embassy. The West Metropole ambassador got up today and decided to deposit something important into the bank, or maybe withdraw something important the bank currently has custody of. Now your players have an entirely different faction and general higher security to deal with, especially if the ambassador is trying to withdraw the same thing everybody's there to steal.

You should always understand the reason behind something when you put it into your game, even if it's as simple as a surprise guard patrol. When you understand why it's there, it makes it easier to understand the orthogonal consequences you might bring down on the PCs and the ways it might have further narrative impact down the line.


The Hiccup.

In heist movies, a moment of tension is often a hiccup in the plan that is almost instantly overcome by quick thinking, skill, or pure luck. A guard walks up, instants from seeing the entire heist team frozen in the bank vault, yawns, and just keeps walking. The shift changes, but the guard forgets his keys, and comes walking back - luckily the contortionist is able to shove himself into a cabinet in record time, etc.

This is a common trope of the genre. The serious twists however don't tend to be 'bad luck' based like that. They specifically require longer sequences to resolve, which sometimes come with their own hiccups or additional complications. The vault door, for example, is a different model than they were expecting and they cannot drill it - it needs a key kept in the manager's office to 'disarm' the explosives inside first. This is not something you can instantly bypass with a single roll (or set of rolls). Someone needs to come up with a new plan on the fly, execute it, roll, succeed, and then you have the key.

Complications that can be resolved with a single roll vs complications that require a sequence of events to resolve are also part of regular adventuring - as the GM you already should be introducing these in non-heist situations, and only need to adapt that method of thinking to stealthy, highly-planned thefts to create appropriate content. Short-duration hiccups are part of encounters, 'yes, but's like 'yes you can swing on the chandelier, but it's old and rickety and might fall down - stranding you in the middle of the duke's men', meaning someone might need to think quickly to save their friend who is now surrounded after a bad roll. Actual complications, like the vault door in the heist movie, are entirely new encounters. Getting all the way to the manager's office past several guards and employees and a laser security system is a new encounter, or even a minor sidequest. It is a complication on the order of the party returning to their employer with the Head-Dress of Gongarra and finding the inn room broken into, blood on the bed, and a goblin knife stuck into the dresser. Now to complete the mission, they must find their kidnapped employer (or confirm his death and find a new buyer). Which entails some investigation and fighting the goblin assassin guild etc etc etc. 1-3 Encounters.

Heist movies play with these tropes a lot - Ocean's Eleven is full of false complications that are actually part of a deeper plan, and then actual deviations from the plan that are not new complications but rather personality issues of the thieves involved etc. You don't really need to do this (although you can) as often ttrpgs go a bit simpler than scripted movies due to the audience participation/puzzle effect. But if you want an actual complication, it must be something that requires the party to effectively deal with a new encounter - and a good rule of thumb for encounter design is that if the party can bypass it with a single roll, it's not necessarily a great encounter (or should be treated as only part of an encounter). The clever plan exception to this is that if the party comes up with a particularly clever plan, it may be fine to have them overcome an entire encounter with a single roll (or only very few rolls, or even no rolls at all), as rewarding clever plans is excellent GMing.

It is to a significant degree a judgement call as to what will require multiple rolls + a plan of some kind to overcome and what is a trivial hiccup that can be defeated with a single roll, but that kind of judgement is a pretty key GMing skill. There are reams of advice online about encounter design, my personal favourite being the ones from the Alexandrian. But since they cannot know your party composition, the psychology of your players, and all those little details only gained by being the actual person there, it ultimately comes down to the GM in question to make those decisions (and meddle with things on the fly to change it if you build it wrong).


Why are you ruining the players' success?

Do you do this when they have a streak of good luck with combat rolls?

Sometimes, everything just clicks and that can be enormously satisfying and fun for the players. Bear in mind that while you know everything is going to go smoothly, they don’t. They’ll have all the suspense waiting for the twist and then be elated when it doesn’t happen.

Perhaps the issue is that you’re scared this will ruin your fun? If so, just let that go and enjoy the players' fun. Sooner or later the rolls will turn and they’ll have all the your kind of fun they can handle.

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    \$\begingroup\$ I believe that continuous success makes the game boring for players, but we should ask the OP. \$\endgroup\$
    – enkryptor
    Commented Jan 31, 2022 at 9:16
  • \$\begingroup\$ @enkryptor I don't think OP would know the answer. OP can ask their players, perhaps, but I really don't think asking OP will, by itself, reveal correct information. \$\endgroup\$
    – VLAZ
    Commented Jan 31, 2022 at 9:41
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    \$\begingroup\$ -1. Makes heavy assumptions not supported by the question. Equates success to fun, which reams of GMs/advice/articles say to avoid. \$\endgroup\$
    – user2754
    Commented Jan 31, 2022 at 11:54
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    \$\begingroup\$ As a player, I think that I would be incredibly disappointed if everything went exactly according to plan---I think that it robs the scenario of some of its tension and (therefore) satisfaction after the fact. I would almost expect that we would, for example, get to the safe, expecting an RDX Deluxe with thumbprint scanner, only to find out that the safe is actually an RDX Ultima, which requires a retina scan, too. \$\endgroup\$ Commented Jan 31, 2022 at 18:19
  • \$\begingroup\$ I explicitly said I have no interest in ruining their success. I haven't done so, and I'm not going to do so. But both my players and I agree that having to adapt and change to circumstances is fun, especially and particularly when it comes to heists. Things going according to plan is a relief, but not fun. \$\endgroup\$ Commented Feb 5, 2022 at 2:35

If there is no chance the outcome is changed, don't roll for it

A dice roll represents a chance, a measure how good or bad you perform at a task that has a chance of failure and/or success. If it is impossible, don't roll for it, simply declare you fail or narrate they realize it is impossible.

But be careful with unavoidable obstacles, for if the players are allowed to roll for something and still fail with spectacular rolls, you might be accused of cheating or actively working against the players, which is of course not fun for anyone involved.

So if something is impossible, just make it clear that is the case, without rolling any dice. Let the players think of a plan B since their usual way doesn't work out as planned.


I'm going to challenge the framing of this question a bit: OP did "force them to improvise" (granted, the sample improvisations were pretty straightforward).

It's important to remember the tremendous information asymmetry most TTRPGs have between the GM and the non-GM players (which, OP's question seems to assume such a setup).

As the GM, you know that a quick "be sneaky" check can wholly bypass an encounter, but the players don't know that.

As a player, you hope that a quick "be sneaky" check can bypass the complication that's just come up, but you don't know (a) that that's the case, (b) how hard that check will be, or (c) what the consequences for failure are. You also don't know what other surprises are lying in wait. While the player who stumbled into the path of the unexpected guard is confirming that there's a good hiding spot and actually rolling the dice, they - and the rest of the players - are quite likely running through backup plans in their heads: can they restrain/kill the guard quietly? should they try talking their way past the guard? can they lie about being lost on the way to the bathroom and try again tomorrow? if a fight starts, how big will it get and screwed is the rest of the plan?

As a player, I'd also want to know how the guard was missed: did our source lie (and, if so, what else did they lie about)? did the scout just miss the guard (and, again, what else did they miss)? is something special going on today that warrants extra guards (and, surprise, what else does that event warrant)?

I suspect that OP's players have a very different recollection of the heist than OP does: they remember how lucky they were that they could sneak past that guard, etc. - how well they handled the unplanned, unexpected complications!

To directly answer the question: it depends on how the party got its information and what the sources of the surprises are.

  • If the party scouted ahead, casing the place on their own, they'd have to have screwed up pretty hard for a surprise vault door to appear.
  • If the party paid an informant, said informant could have been lying about their access or the degree to which they're willing to sell out the ... casino? ... for that extra vault door to appear.
  • Extra guards are easier to explain: a VIP high-roller might have body guards; inspection day might see extra guards either just for show or to offer extra protection since the inspection will see valuables in nonstandard locations or just see a lot more people in the secure side of the building.
  • Other security upgrades (upgrading from a palm reader to an iris scanner, perhaps) should probably have some foreshadowing to avoid their becoming screwjobs (good intel might include that there's a new security head looking to beef up security and the new locks are just a bit ahead of schedule; bad intel might result in noticing day-of that the guards are all new).

Add a few twists

Whenever I do a heist, I always make sure to add a few twists.

Here are some I've used.

  1. Some guards are somewhere inconvenient that they shouldn't be. They're decided to take a smoke break there, and the PCs need to handle them somehow, or exploit the hole they left in security.

  2. There's some valuable loot on site that will substantially increase the reward of the job, but it's risky to grab it.

  3. Someone valuable and important to them is in the site with key info being interrogated/ tortured.

  4. A rival corporation has decided to send a kill squad to the place to kill everyone inside.

  5. There's some sort of sentient robot/ monster inside which if released could be a friend or a distraction or an enemy.

  6. Some evil act is happening inside involving people which will earn the team a lot of social credit if they stop.

  7. An external force like a monster attack or a storm is happening that messes up procedures.

  8. The valuable data is gone. The corporation is bankrupt, and the employees seeking better opportunists have stolen it and put it elsewhere in the building.

  9. The employees are actually aliens/ russian spies/ an interdimensional horror, and a plan to hurt the community is visible.

  10. It's surprise bring your children to work day, and there's a bunch of kids running around the site.

Any or all of these twists can make the heist more fun without relying on bad dice rolls.

As others have noted you can just do twists that are basically bad things happening, but you can also have twists that work even if everything goes perfectly. I've found that players often get annoyed if all their hard work with dice is ignored in favor of rail roading some bad encounter.

So instead if they roll perfectly, it's often better to make the random events things that could be good or bad for the players. A twist to make them adapt, but not a bad thing. It might be a good thing that the manager is stealing the cash, because the safe in his office is much less secure than the main safe say.


Make a twist unavoidable.

If you feel there must be a twist, set up your twists that can be avoided by great rolls, and set up one that can't be bypassed simply by rolls. Not everything in the game should be able to be dealt with simply by character abilities and skills; narration is a big part of the game.

In the case of your guards, it is reasonable that there's no chance to sneak past them. That doesn't force the players to fight necessarily, but they might be forced to improvise, if they want to avoid detection or alarm.


Use a Drama Dice

I introduced a Drama Dice in my game system, that introduces a mechanic to inject a scene with dramatic events etc.

Every player rolls an extra d20, with every single roll. This extra die does not contribute to the final roll. We can safely discard its result, unless it's a 1 or 20. 1 is Bad Drama, 20 is Good Drama.

If a player rolls Good or Bad drama, then the can reflect this in the scene. It should be noted that drama doesn't have to happen at the moment the player makes the roll.

For example, Bad Drama on one of those sneak rolls, could mean that one of your players accidentally leaves a fingerprint, or tiny bit of evidence that will later be discovered by investigators.

I really like this drama mechanic because you can create some very interesting scenarios. I should also note that you can use a d10 if you want drama events to happen more often, and even though I've not done this in my games, I can see a scenario where you may want to make higher stakes scenarios use higher stake drama dice.

I have an example of this in my home-brew docs: https://www.node10.info/system/rules.html#drama-dice-example

  • \$\begingroup\$ +1 I like the idea - but I think my other half ate all my drama dice. :) \$\endgroup\$
    – Thank-Glob
    Commented Feb 4, 2022 at 20:56

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