How to Use Failed Rolls to Spark Storytelling Opportunities

What if failure was the most interesting part of your session? That question echoed in my mind after running A Stitch in Amber, a stealth-driven one-shot set deep in the Feywild. The dice worked against us—roll after roll came up short. The party struggled to move quietly, persuade allies, even land their blows. Instead of tension, we got stalling. It was the perfect storm of failure in Dungeons and Dragons. Instead of drama, we got frustration.

It reminded me of a problem I’ve long known but hadn’t fully wrestled with: when the dice say “no,” the story often stops. And it’s not just as a DM. Before running A Stitch in Amber, I was playing an artificer who encountered the perfect narrative moment—a mechanical musical book that needed repairing to unlock the next chapter of the story. It was tailor-made for my character’s abilities. Three rolls were called for. I failed all three.

What should’ve been a moment of spotlight and growth became a narrative brick wall. That moment stuck with me. Because this is the core issue: DMs need tools to flavor failure, yes—but system designers need to recognize that mechanical failure without narrative flexibility can break immersion and fun entirely.

Why Failures Feel Flat

In fact, this issue has been explored in depth by other creators too. Matt Colville addresses a similar point in his excellent video “Failing Forward”, where he breaks down how a game master can treat failure as an opportunity to make the story more interesting, rather than shutting down the action. His framing is a perfect companion to the techniques explored in this article.

In Dungeons & Dragons, most rolls are binary. Either you succeed, or you don’t. When you fail, the default outcome is usually silence:

• You fail to pick the lock. The door stays shut.

• You fail to sneak past the guard. You’re spotted.

• You fail to persuade the noble. They say no.

It’s clean, but it’s rarely satisfying. Repeated enough, it grinds a session into a slog.

Players want drama, not dead air. So how can we reframe failure to keep the story alive? So how do we give them that—even when the dice are ice-cold?

Story-First Tools to Spark Creativity and Narrative Opportunity

1. Fail Forward

Instead of “you can’t,” think “you can, but…” The goal still happens, but at a cost.

• You unlock the chest, but your tools snap.

• You scale the wall, but drop your pack halfway up.

2. Partial Success

Even a failure can yield something:

• You don’t persuade the guard to let you pass, but they reveal what worries them most.

• You don’t silence your steps, but you overhear a clue before being noticed.

3. Consequences Over Blocks

Make failures change the situation instead of stopping it:

• The rope doesn’t hold, you fall, making noise that alerts nearby creatures.

• Your spell fizzles, but a strange resonance attracts a new magical presence.

4. Spotlight Characters

Failures can reveal flaws, quirks, or vulnerabilities:

• The rogue trips, not just noisy, but muttering a curse that shows their impatience.

• The cleric stumbles in persuasion, blurting out a personal belief that deepens roleplay.

d6 Tables of Flavored Failures

Sometimes you don’t have the energy to improvise in the moment. That’s where a simple tool helps: roll a die and flavor the failure with inspiration. Here are a few to try tonight.

Stealth Failures (d6)

1. A sudden noise from the environment betrays you. A branch snaps, a stone clatters. The sound echoes unnaturally, drawing a creature’s curiosity, but not yet alarm. You have one action before they investigate fully.

2. Someone nearby notices something odd. Not you, but a shadow or echo. They call out, alert but uncertain. You now have to stay still, hide better, or create a distraction.

3. You stumble and drop something small, perhaps a coin or charm, that rolls into view, catching a glint of light. Someone begins to approach. If they inspect it, your cover may be blown.

4. Your movement exposes another ally, drawing danger their way. They must act quickly or risk discovery. You remain hidden for now.

5. You’re briefly seen, but mistaken for a harmless creature or servant. The observer is now alert and more likely to investigate oddities.

6. Your clumsy step distracts the enemy, though you’re noticed, the shift in attention gives another player an opening or advantage.

Skill Challenge Failures (d6)

1. You succeed, but it takes longer than expected. Time-sensitive consequences now loom.

2. You succeed, but at a cost, a tool breaks, or a resource is consumed unexpectedly.

3. You fail, but in doing so, uncover new information, a hidden symbol, clue, or secret you weren’t looking for.

4. Someone witnesses your struggle, now there’s added pressure, scrutiny, or interference.

5. You partially succeed, the door opens, but with a loud creak, or the path is revealed, but it’s unstable.

6. Your effort shifts the scene, dust rises revealing old markings, a rock shifts revealing a cave, or the ground destabilizes.

Bringing It Back to Amber

If I could rerun A Stitch in Amber, those repeated stealth failures wouldn’t have been dead ends. Each could have made the Feywild feel more alive:

• A snapped twig echoing through amber caverns.

• A dropped trinket glowing faintly, drawing fey insects.

• A guard alerted, not by sight, but by the sweet tang of pollen drifting in the air.

These details wouldn’t erase failure, but they’d turn it into story.

Creativity Over Calculation

Failure in Dungeons and Dragons isn’t a dead end, it should be creative fuel. When players and DMs embrace it together, failed rolls become a shared invitation to improvise, react, and reveal. They’re story seeds, not walls. With just a little prep, or a handy table, you can turn disappointment into drama and hesitation into heat. When you shift your mindset from punishment to potential, every roll, win or lose, adds to the tapestry of your game.

Let the dice misbehave. Your story doesn’t have to.

And if you’re ready to go deeper, Part 3 of this series will walk you through “A Stitch in Amber”, a one-shot adventure that uses everything we’ve explored here. With built-in failure flavor and story-first tools, it’s designed to keep the drama alive even when the dice aren’t on your side.

While I work on the final part, If you haven’t already check out my post Stealth in Dungeons and Dragons it’s where I started this journey, where the dice failed me and my interest was spiked.