In TTRPGs, the difference between success and failure often comes down to the roll of a die. This article explores why embracing failure, rather than constantly mitigating it, creates more meaningful and engaging gameplay experiences.
While DMs may be tempted to shield players from failure through mechanical advantages, genuine failure creates narrative tension, character development, and meaningful challenges that ultimately enrich the TTRPG experience.
It's sometimes disheartening to watch our players strategize brilliantly only to have their plans foiled by an unlucky die roll. Equally frustrating is seeing a particular player consistently miss throughout a session with few options to recover. During these moments, we're tempted to invent ways for players to reroll or gain Advantage retroactively (perhaps through a delayed "help" action) to help them succeed.
Background
Recently, I joined a game with a wonderful group of folks of varying experience levels—some were complete beginners, others had played a few times, while the DM was quite experienced. The adventure centered around a dragon fight in an elegant castle filled with dangerous traps. Beyond navigating these hazards, we faced two major battles: one against several suits of animated armor and the final confrontation with the young dragon itself.
At Level 4, player characters typically have a hit modifier of +5 or +6. Against creatures with 18 AC (which both the armor and dragon had), this gives players only a 40% or 45% chance to hit, respectively. Without the Extra Attack feature that martial characters gain at level 5, players naturally miss more often than they hit. However, during each battle, the DM clearly wanted players to succeed and actively tried to prevent misses. One effective approach was allowing us to target specific parts of the animated armor, so powerful hits would damage the armor and reduce its AC. This made combat progressively easier while giving players agency to influence outcomes through a "rule of cool" approach. It was a cool implementation that worked.
Yet the DM went further in their effort to minimize misses, distributing Advantage liberally and without justification. When a player would miss despite having Advantage, the DM would roll on the Wild Magic Surge table, hoping for effects that might either help the player or enable another attack—further demonstrating their determination to prevent player failure.
I understand the DM's motivation: ensuring players enjoyed themselves and that the one-shot's story progressed due to time constraints. However, handing out such bonuses ultimately lowers the stakes of any story. If players cannot fail, where is the risk or the opportunity to overcome genuine challenges?

How Failure Tells a Story
In TTRPGs, failure is not just a mechanical outcome—it's a powerful narrative tool. When players miss attacks or fail skill checks, these moments create tension, reveal character, and add depth to the story being told collectively at the table.
Failed rolls provide opportunities for:
Character Development - How a character responds to failure reveals their true nature. Does the fighter become frustrated after missing several strikes? Does the wizard second-guess their abilities? These reactions build personality and depth.
Highlighting Success - Victory means little without the risk of defeat. When players finally land that critical hit after several misses, the triumph feels earned and significant.
Creating Tension - A combat where every attack succeeds might lack drama. Misses build suspense and keep players invested in the outcome.
Showcasing Enemy Prowess - When players miss against formidable foes like dragons, it reinforces the narrative that these creatures are truly dangerous adversaries worth fearing.
While it's understandable to want players to succeed and have fun, constantly mitigating failure through mechanical advantages robs the game of meaningful challenge. A balanced approach where players sometimes fail, but those failures create interesting narrative developments, enriches the storytelling experience for everyone at the table.
When Players Feel Cheated by Failure
Many players, especially those new to TTRPGs, can find repeated failures discouraging or even frustrating. After investing time in character creation and emotional energy in roleplay, it's natural to want success more often than not. Some common player reactions to persistent failure include:
Disengagement - Players may check out mentally, believing their contributions don't matter if the dice are against them
Rules Lawyering - Searching for mechanical advantages or loopholes to overcome the randomness of dice
Risk Aversion - Avoiding creative or risky actions in favor of "safe" options with higher chances of success
Character Abandonment - In extreme cases, players might want to retire or kill off characters who consistently fail
These reactions are understandable, but addressing them by eliminating failure altogether creates its own problems. Instead, we need to reframe how failure functions in our games and help players see its narrative value.
Failing Forward: How Failure Propels a Story Forward
Failing Forward is a narrative technique with a simple premise: failure in an action or task still progresses the story in a meaningful way. In games, we often think of failure as a dead end or roadblock. A rogue fails their Dexterity check to pick a door's lock and now can't get into a restricted area. The wizard botches their Investigation check and doesn't find anything in the town's library.
Instead of halting the game when failure occurs, we can introduce new challenges, complications, or opportunities that keep the narrative moving forward. For example, what if the rogue's failure catches the attention of a nearby guard (new challenge), or another player feels encouraged to cast the Entangle spell to grow roots in the lock to force it open (new opportunity requiring a "rule of cool" ruling from the DM). The wizard may not find the book they want, but a helpful librarian comes over to see if they can help (new complication).
Whether success or failure, we want to give our players morsels for their efforts. Throwing these kinds of elements at the players isn't always pre-planned and can be done on the fly.
Applying "Failing Forward" to a Skill Check
Let's say our players need to climb a high wall to escape a pursuing enemy or reach an important objective. The DC to successfully climb the wall is 18. Meaning, they must roll an 18 or higher to bypass this challenge.
DC 0-9: Initial Failure: The character begins to climb but quickly loses their grip and falls to the ground. They suffer 1d6 bludgeoning damage. A nearby monster hears the noise and starts approaching (new complication).
DC 10-14: Partial Success: The character makes some progress but encounters loose stones about halfway up. They slip and hang precariously, losing their grip but catching themselves just in time. They are now in a more difficult position, requiring a higher DC (20) for the next part of the climb, but they notice a small ledge to rest on if they succeed (new challenge).
DC 15-17: Near Success: The character almost reaches the top but encounters an overhang they didn't anticipate. They lose their grip and slide back down a few feet. They are now aware of the overhang and can attempt a different approach, making the climb easier (DC 16) for subsequent attempts (new opportunity).
You can see how various challenges, complications, and opportunities are slotted in which require players to work together or come up with imaginative solutions to their problems. It’s far more interesting than, “You fell off the wall taking 12 points of bludgeoning damage, try again.”
Applying "Failing Forward" to Combat
The Failing Forward concept applies equally well to combat encounters. When players miss attacks, rather than arbitrarily granting Advantage to ensure hits, consider how those misses can create meaningful narrative opportunities:
Contextual Advantages - If you want to grant Advantage where rules don't explicitly allow it, tie it to something happening in the scene. Perhaps the fighter's missed attack caused the enemy to lose balance, giving the rogue Advantage on their next attack.
Environmental Effects - A missed fireball might ignite nearby tapestries, creating new tactical options or hazards that change the battlefield dynamics.
Enemy Reactions - When a player misses, describe how the enemy reacts with overconfidence or reveals something about their fighting style, offering strategic information to the party.
This approach differs from simply preventing misses through mechanical handouts. It acknowledges the miss but ensures it contributes something narratively meaningful while maintaining the integrity of the game's challenge.
Putting "Failing Forward" into Practice: An Investigation Check Example
In one of my recent sessions, I implemented a failing forward approach to an investigation scene. The players were searching a study for clues about a mysterious noble they suspected of criminal activity. Instead of a binary success/failure system, I created a tiered information structure based on different DC thresholds.
The DC to discover everything was 18, but players would learn something useful regardless of their roll:
DC 0 - Basic Observation: A portrait showing the noble with several unknown figures at what appears to be a secret meeting. One face is deliberately obscured in the painting.
DC 10 - Desk Contents: Correspondence revealing the noble's business dealings with merchants from neighboring kingdoms, including some coded language about "special shipments."
DC 15 - Hidden Compartment: A false bottom in a drawer containing a map with several locations marked, plus a ledger with payments to unknown recipients identified only by initials.
DC 18 - Secret Safe: Behind the bookshelf, a concealed safe containing incriminating documents linking the noble to a smuggling operation and the names of co-conspirators.
Funny enough, when I ran this in my session, my investigating player rolled a natural 1 (a critical failure) with a -1 modifier, so basically a zero. Lo and behold they still got something for their time and I also prompted them to roleplay how they messed up so badly, creating an enjoyable moment for the table. The rogue later rolled much better and found the hidden compartment, creating a satisfying progression of discovery.
What made this approach effective was that each tier of success built upon previous discoveries, creating a coherent narrative regardless of roll outcomes. Players felt rewarded for their efforts while still experiencing the tension of potentially missing crucial information.
It's Okay for Players to Just Miss
Sometimes, a miss is just a miss—and that's perfectly fine. Combat should feel dangerous and unpredictable; missing is part of what makes success meaningful. When players experience the full spectrum of possible outcomes, from critical failures to spectacular successes, their investment in both the battle and their characters deepens.
Misses create natural ebbs and flows in tension during combat. They build anticipation for when a hit finally lands. They provide opportunities for character development as players react to setbacks. Most importantly, they preserve the stakes that make victory satisfying.
As DMs, our job isn't to ensure players always succeed, but to ensure they always have interesting choices to make—even when the dice aren't cooperating. By embracing both success and failure as equally valuable parts of the story, we create more memorable and meaningful experiences at the table.
Coming Soon: One-Shots vs. Campaigns—Different Approaches to Failure
I'll be writing a future article examining how our approach to player failure might differ between one-shot adventures versus ongoing campaigns. In one-shots, where time is limited and players may never return to these characters, there's a legitimate argument for mitigating some failures to ensure a satisfying narrative arc in a single session. Conversely, in campaigns, embracing failure can create rich long-term character development opportunities and meaningful story arcs that unfold over many sessions. I'll explore how DMs can balance these different contexts while still preserving the valuable tension that failure creates, when it's appropriate to be more generous with success, and when we should let the dice fall where they may.
Stay tuned!
Just like da gym! Fail = Success *flexes like a half-orc*