Steal This Rule: Flashbacks and Heists in Dungeons & Dragons

In a heist film, a group of experts team to overcome elaborate security measures using a carefully planned series of steps. Much of the fun comes from seeing the ingenuity of the heroes as they crack seemingly impenetrable obstacles as if they were puzzles.

Roleplaying games such as Blades in the Dark and Leverage offer rules for adventures centered on heists.

As an activity for a roleplaying game, heists pose two challenges:

  • The exhaustive planning behind a typical heist would tax the patience of gamers eager to jump to live play.

  • The characters in a heist have more experience and expertise in the game world than the players can match. These characters can plan for trouble that surprises the players.

Heist games use a flashback mechanic to substitute for the planning players would rather skip and the expertise they lack. Players can call for a flashback to do preparations in the past that affect the current situation.

In my last post, I suggested using flashbacks as a formal way to allow players to pause the action and work out the strategy that their expert characters would have planned earlier.

For Dungeons & Dragons sessions where players attempt a heist, adding a flashback rule helps capture the feel of a well-planned caper.

When players face an obstacle, they can call for a flashback and describe a past action that impacts the current situation. For example, if the characters face a cult priest who demands to see the tattoo that shows their cult membership, they could flashback and narrate the scene where they forged the mark. This might require a deception roll to pass the priest’s inspection.

Flashbacks don’t work as time travel. The players couldn’t flashback to the scene where they killed the priest—he stands in front of them.

As a dungeon master, you might require an Intelligence check to determine if the character anticipated the situation and did the proposed preparation. The more unlikely the circumstance, the higher the DC.

As a price for a flashback, you can claim a character’s inspiration, take DM’s inspiration to spend on a villain’s roll, or both. The price of a flashback might start at nothing, and then rise through the game session.

Flashbacks make a lightweight mechanic that you can easily adopt for a session focused on a planned mission.

12 thoughts on “Steal This Rule: Flashbacks and Heists in Dungeons & Dragons

  1. Matthew Neagley

    I beg to differ. The player absolutely COULD flash back to when they killed that priest, knowing he would impede them at this moment.
    Yet here he is. Was he brought back to life? Is this a similar priest? The vengeful dead? Is there something wrong with the character’s memory?

    Seems like something that shouldn’t be done often, and has the potential to really monkey wrench shit, but seriously, how cool would that be?

    1. Joshua

      Hear-hear: maybe DM spends their inspiration to add the double-twist? Or uses a number of twists equal to CR or heist target leader’s INT mod or something.

    2. mAc Chaos

      My reaction to that is, why would the player waste their resources on flashing back to kill the priest then, if the priest is still obstructing them there.

      Of course, for pure PR potential it is good.

  2. Curtis Costello

    In our games, we’ve come up with a system of “contrivance points” that players can spend to add in plot, and maybe stretch credulity. I might add flashbacks as another use for these points

  3. Michael Lush

    The Netflix series 3Below (The Arcadian Job) had an interesting ‘flash forward’ spin on this.

    The protagonists need to break into a high security military base, but the action focuses on the planning session where they narrate what they are doing and what they say appears on screen ie

    We infiltrate under cover of night and cut through the wall with BZZZZZZT!!! No no can’t do that! Look the the wall is electrified…

    We infiltrate under cover of night, short circuit the wall with (failed Security roll) Alarm rings guards show up instantly and they die in a hail of blaster fire! No no can’t do that…

    OK . infiltrate under cover of night, insulate the wall with rubber matting (rolls a success) and climb over the ZAP!! Oh sentry turrets

    Hmm the wall is a bust, how about the gate?

    Once they are through all the security it switches back to normal ‘real time’ play.

    From a GM POV I would probably toss a coin for each area they travel through (ie We infiltrate under cover of night (heads, no minefield) and cut through the wall (tails deathtrap) so you get an interesting narrative of all the perils encountered, avoided or circumvented without the tedious cavern crawling “I move forward 10ft and check for traps” play.

    (actually if you have Netflix I’d highly recommend Trollhunters and then 3Below (Del Torro productions!!))

  4. lunaabadia

    One of the mechanics I really like in Gumshoe games such as Night’s Black Agents is the Preparedness skill. It represents this concept that your character has a knack for planning. As with other skills in the game, you spend one or more points to add to a roll for what you are trying to accomplish. You might say, “but of course I brought night goggles,” and you make the roll. As you noted above, the whole point is to zip past the boring hours players can spend wondering what gear to bring. Preparedness answers the question of whether you brought it and frees players’ brains to focus on the action.

    I would guess that could be done with Inspiration, and in a heist session it could make a lot of sense to give each player Inspiration at the start of the mission, representing their planning. Do you spend it on a roll? Or do you hold it in case you need to do a flashback? You don’t get advantage on any rolls during the flashback. You just get the flashback.

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  6. Browncoat Jayson

    I like the concept, but I don’t want to tie it to Inspiration. I’ll probably make it a variant of the Plot Point rule in the DMG, and probably use a downtime activity as the way to gain points (rather than just starting everyone with one).


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