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Steal This Rule: Flashbacks and Heists in Dungeons & Dragons

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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.