How to Avoid Boring Rerolls of D&D’s Ability Checks

Dungeons & Dragons plays best when players can only retry ability checks if something changed after the first roll.

For many ability checks, this makes sense because failing makes trying the same thing again impossible. The Dungeon Master’s Guide gives this example: “If the rogue loses a contest of Charisma (Deception) against the guard’s Wisdom (Insight), the same lie told again won’t work.” Typically, Intelligence and Charisma checks only allow one attempt.

Still, the realization that DMs should avoid allowing rerolls surprised me because some checks naturally invite retries. Typically, Strength and Dexterity checks seem open to multiple attempts. Why not try to pick a lock again? The Dungeon Master’s Guide even includes advice for multiple checks. “In some cases, the only real cost is the time it takes. To speed things up, assume that a character spending ten times the normal amount of time needed to complete a task automatically succeeds at that task.”

That suggestion seems like advice for retrying checks, but at the core, it tells when to skip them. If a character can succeed and has time, then skip the roll. This guideline never explains how to determine whether characters have enough skill and talent to succeed. (Spoiler: I will recommend rolling a check.)

DMs aim to run an exciting game, and skipping rerolls helps. The outcome of a roll should launch—or at least nudge—the game ahead or into a new direction. Even a failure that blocks progress should inspire ingenuity. If a failure does nothing more than prompt a player to fish for a higher number, then the game stalls. Boring. Third edition even created rules to avoid such fizzles. A player could take 20 and spend 20 times as long in exchange for an automatic 20 on a check attempt.

For checks that seem to allow multiple retries, the take 20 rule answers the can-I question using addition. While fifth edition skips the take-20 rule, the math remains the same. If a character’s check bonus plus 20 meets or beats a task’s DC, then mathematically the character could succeed. But this take-20 math leads to unsatisfying play for two reasons:

If bending the bars of dungeon cells requires success against a DC 20, which the game calls “hard,” then anyone with an average Strength of 10 and time to spare gets loose. The same goes for a hard lock and an untrained thief with no aptitude. For dungeons to hold athletes and locks to deter thieves, the iron and the mechanisms need a DC 25 and talented beginners still get through. I think we can all agree that prisons work better than that. But we contrive DCs to create a fun and challenging game. D&D aims for heroics where the barbarian bends the portcullis and the rogue picks the lock, all before the approaching monsters arrive. So the game recommends DCs based on the assumption that characters only get one attempt.

Instead of using take-20 math to decide whether a character has enough talent and skill to succeed, the game usually plays better when one ability check decides. Knowledge checks already work that way. When players ask if their characters know the history of Netheril, a check answers without rerolls or taking 20. For any check where failure blocks a retry, one die roll decides whether a character can succeed. Can the paladin persuade the mayor? Can the wizard decipher the sigil?

Checks that decide what a character can accomplish date back to first edition and attempts to bend bars or lift gates. “The attempt may be made but once, and if the score required is not made, the character will never succeed at the task.” Does a failed check reveal thicker bars? Maybe. Such checks fit D&D’s long tradition of rolling to learn things about the game world, things like whether a door is locked or if the skies are clear.

Die rolls bring more fun than letting take-20 math or a DM’s ruling decide between success and failure. Plus, you only roll once so the game never stalls while someone fishes for a higher number.

Now that you know to never allow a character to repeat a check, I will weaken that principle by revealing exceptions.

One obvious exception: Sometimes a change in approach allows a reroll. If a character failed to move a stone, perhaps a lever will help. Gain another attempt.

The second exception requires a DM’s judgement, something right in the DM job description.

When characters risk paying a price for failure, allowing retries can create a more exciting game. If a climber can fall or if someone attempting to disarm a trap can suffer the device’s effects, the character can retry and bear the risks again. Often the price of failure comes from losing time against a ticking clock—a draining hourglass in most D&D worlds. In classic D&D games, every moment wasted raises the risk of wandering monsters. When attempting to break a door, the price of failure is often noise, whether it alerts wandering monsters or nearby guards.

Fifth edition allows for setbacks more interesting than damage or delays. Failure can mean that a character “makes progress combined with a setback determined by the DM.” For example, if a rogue blows a roll to pick a lock, the DM can decide that the lock opens but the attempt made a noise that leads to complications. Gamers call this failing forward.

The Call of Cthulhu roleplaying game includes a “pushing the roll” rule that lets players agree to pay a price for a second failure in exchange for a retry. Players describe the extra effort or time taken to justify a second chance. Plus, they give the game master “permission to bring dire consequences” if the next attempt fails. You may steal this rule for your D&D game. The idea works especially well for checks with a potentially harsh penalty for failure. For example, a character who fails a first climb attempt realizes the cliff seems too treacherous and makes no progress. If the climber pushes on despite the risk, and then fails again, they fall.

DMs who ask for a check must be ready for failure. Sometimes even published modules include checks where a failure blocks the rest of the adventure—checks with no room for failure. At conventions, I have seen bad rolls test DMs who abruptly realized that a failure left the adventure no way to continue. These DMs switched to improvising new checks as a way to drag the group to success. When we kept failing, the damage control turned comical. Failing forward lets characters fail checks and still pass ahead, but search checks and especially knowledge checks can make inventing a setback a hard challenge for a DM.

Related: In D&D, Letting Everyone Roll Certain Checks Guarantees Success, So Why Bother Rolling?

7 thoughts on “How to Avoid Boring Rerolls of D&D’s Ability Checks

  1. EarlobeGreyTea

    The computer RPG Disco Elysium uses the “try, and try again when you get better” mechanic you mentioned. Failed skill checks are recorded, along with an indication that you can try them again when your stats improve or you have an item that helps. Not all checks are like this – some result in permanent failure, but things like forcing open a door fall into this category of being able to retry when you have a tool to help.

  2. Ilbranteloth

    We’ve used variations for years, and 5e helped simplify the options even more for us.

    First off, we have passive skill checks. That’s basically the same as take 10. That gives a baseline for what is easy for you and doesn’t really need a check unless the circumstances alter your chance of success. For example, passive Stealth against passive Perception. Some folks seem to get bent out of shape when I mention a rule like this, but consider that a deer is naturally far stealthier than a person, even when they aren’t trying to be. That’s an example of a higher passive Stealth.

    We also use the Take 20 mechanic when there is time to succeed.

    We do take into account trained vs. untrained, etc. as well, but it’s not important right now.

    You raise the issue that many things will be successful all the time because of the DCs. We feel the DCs in 5e are too low, and adjust them accordingly. At the very least, most need to be 5 points higher. But certain trope-y things (bending iron bars to escape a cell) are much more difficult, as they should be. My players prefer things to be more ‘realistic’ so something like breaking out of prison is very, very hard to do. We view failure as a good thing, because it forces the Players/PCs to find other solutions and be creative. We don’t share the same philosophy as 5e that failure is boring or bad.

    But the biggest difference that if the PC is capable of something, then a failed roll provides information for the DM to adjudicate the circumstances. The most common option we use is that the difference between the DC and the failed roll is a measure of time.

    For example, picking a lock is something that is relatively easy for somebody who knows how to do it and come across a ‘standard’ lock. It takes a few moments, but not that long. But what if they are trying to pick a lock to get out of a hallway before the guards come around the corner?

    With the pressure on, they roll a check. In this case we’ll say the DC is 25, but they rolled a 17. Rather than re-rolling, we use the difference as a measure of time. In this case they failed by 8, so it will take 8 rounds for them to pick the lock. The PCs don’t know how long it will take, of course. But it adds a missing piece of the skill check puzzle that also provides information that was previously missing in the system.

    So the PC continues to try to pick the lock, while the lookout is getting antsy because the guards are getting closer. Finally, in round 5, the burly fighter kicks in the door instead. Of course, that alerts the guards and now they’re on the run…

    Depending on the circumstance and task, the measure of time might be rounds, minutes, hours, even days, whatever is appropriate.

    What about something like a trap, you say? You’re attempting to disarm a trap and fail, doesn’t that set it off? I don’t think so, not all the time, anyway. We have different checks for disarming a trap and setting off a trap. That’s built into the description of the trap itself, and the chance increases the more you fiddle with it. If the sensitivity exceeds the skill modifier of the PC attempting to disarm it, then you set it off. Each round you continue, the number increases by 1.

    This can also be used as information to inform the narrative by the DM.

    For example, the PC is attempting to disarm a trap. The DC to disarm is 20, and the sensitivity (chance to set it off) is 2 (not very sensitive). The PC rolls a 16 on their chance to disarm. So the DM knows it will take 4 rounds. The PC has a modifier of +4, though. Which means that if they continue to try to disarm it, they will set it off in round 3. The modified sensitivity is the new base. So if they stop and another PC stops after one round, the sensitivity is now 3, which means that they need to succeed in the first round, or they will set it off.

    Note that it is still quite possible that the trap will be set off on the first failure.

    The same mechanic can be used for other types of checks. For example, if you’re trying to ask a favor of a guard, the initial check sets the stage. The DM decides that the guard loses patience after 3 minutes (which is the measure they determine makes sense for this interaction), so if the check fails by 4 or more, then the conversation plays out until the guard loses their patience.

    So what if the PC tries to overcome the guard’s impatience? Such as offering a bribe. Sure, you could call for another check, but that doesn’t take into account the prior check. Instead, use that as a modifier, based on the guard’s disposition and circumstances. For example, if the guard is likely to be swayed by a bribe, then it gives the PC advantage, and a +5 to the existing roll.

    If the original roll missed by 9, then after three minutes the guard has lost his patience. The PC quickly offers a bribe, and the guard is listening. That grants the PC another 5 minutes to the attempt, but it’s still short by a minute, and ultimately fails to sway the guard.

    We also use degrees of success and failure, success/failure by 5 or more, 10 or more, etc. In the guard scenario, the initial failure was by more than 5. So if the PC continued to press, without altering their chances, then the guard would have become more irritated, and potentially remembered the encounter beyond the initial one. If they were offended by the bribe attempt, they might have immediately called for assistance, and arrested the PC.

    However, if they were interested in the bribe, but they still declined (failed by 1), then future interactions could be more favorable, and under the right circumstances a bribe might be taken later.

    1. GavinRuneblade

      “You raise the issue that many things will be successful all the time because of the DCs. We feel the DCs in 5e are too low, and adjust them accordingly. At the very least, most need to be 5 points higher. But certain trope-y things (bending iron bars to escape a cell) are much more difficult, as they should be. My players prefer things to be more ‘realistic’ so something like breaking out of prison is very, very hard to do.”

      I think some of this comes down to what a group (or the developers) define “very hard” and “nearly impossible” to mean. I’m taking a guess here because I haven’t seen the developers say why they set the DCs where they did. But, it appears that they want “nearly impossible” to mean “nearly impossible for a human being living on real-world Earth in the 21-st century; but actually not all that hard for a mid- to high-level PC living in a D&D game world”.

      At one point I totaled up every possible stacking bonus you can get (expertise goes up to +12, bardic inspiration dice go up to d12s, guidance, applying a manual to raise your stat to 22 not just 20, having a feat or class ability that lets you apply a second stat to a skill check, etc.) from a WotC published product. It is possible for high-level characters to get a result of 63 when they roll a 1 on the d20. And there are probably things I missed when I was making my list so the real number might be higher than that. Absurdly unlikely yes. But possible.

      And even if you just assume expertise and +6 from the stat and 2 points from somewhere else, “nearly impossible” happens successfully half the time (11+ on d20). Less with advantage, which is not hard to achieve at high level (burn a low-level spell for enhance ability, for example, or have someone take the “help” action). So clearly, they didn’t mean “nearly impossible for a 17th level character. Unless they think winning a coin toss is “nearly impossible”.

      Some groups, especially those who play at levels 11 and under, will never see a problem with these numbers. Like most of 5e (and every edition) it only breaks at high level. So what does “nearly impossible” mean to your gaming group? Is 30 high enough? What does “medium” mean to you?

      Games have different needs. So thank you for sharing how and why you changed what you changed. I hope it helps other DMs who think the numbers in 5e are off from what their table needs.

  3. gutsdozier

    I like the idea that when the DC for opening something is 15 or less, then a failed roll just indicates how long it takes to open. But if the DC is 20 or higher, a failed roll indicates that the player cannot open it using the same approach. That allows the DM to decide whether they’re creating a challenge that could become an insurmountable block. If the players are thrown in a prison with a DC 20 lock, the DM knows that they’re creating a situation where a failed lockpick check could result in the players starving in prison unless there are other possible means of escape.

  4. Brian D

    Here are two suggestions which may help reduce unnecessary checks.

    1: Base the skill check on the level of the character, as in “only a 7th level wizard would know ‘X’” or “a martial character skilled enough to attack twice a round could do that.”

    2: Bending the prison bars requires a DC 15 Strength check made by a character with a strength score no lower than 16 or two characters with a combined attribute bonus of +4.

  5. Pingback: Stop Favoring Perception for Searches in D&D | DMDavid

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