How Many Times Can a PC Reroll a Check?

How many times can a PC reroll a skill check? Can other PCs help? How does the math of the game change if several PCs try the same check… or cast Guidance or use the Help action? And how frequently should we as DMs ask for skill checks?

But First, Draw Steel!

Just announced: I worked with MCDM and Griffon’s Saddlebage to convert 10 magic items from 5E to Draw Steel. It was a really fun project. (Available to MCDM patreon supporters here.)

It all Started with Pirate Borg

In this first of three blog articles, let’s start with the first question. A question asked on my YouTube’s Pirate Borg video kicked this off:

Let’s say a player has fashioned some kind of grappling hook and wants to toss it to hook onto a rock to try and climb. So you ask for a presence test to see if they succeed in throwing the rope to attach to the rock, and they fail the test. From a storyline perspective they could try several times to get it hooked on the rock so how do you allow for skill checks on actions that could realistically be attempted several times?

This led me to create a video on how many times a PC can reroll a check.

Considering Gameplay

At the surface level, this is a question of whether PCs should be able to retry a failed check, especially when the situation doesn’t prevent it. Generally, games don’t allow rerolls. A thief can try to pick a lock once. In some editions of D&D, the rules said they could try again when they gained a level.

Why can the thief only try once? Because an RPG is a game. Being able to endlessly try without consequence would lead to a lack of excitement in situations where there is no implication for failure.

Even when we think we could sit there for an hour tinkering with a lock, we are choosing the explanation of lock manufacture exceeding our skill for gameplay reasons – the skill check is meant to see if you succeed or fail, and you failed. More on this later.

But, in this case, we have a rope and a grappling hook. We are tossing it up to catch onto a rocky surface. It feels like this should eventually succeed, right?

Yes!

What Does the Roll Represent?

Here we can look to MCDM’s Draw Steel RPG, which has some great language:

The Director should ask a player to make a test only when the player’s hero attempts a task where the consequences of failure are interesting or dramatic, and where failure won’t grind the story to a halt. For example, if a hero wants to leap over a waist-high wall while casually walking through a peaceful city neighborhood, the worst case for failure is probably that the hero falls on their butt, takes no damage, and can stand up to either try again or walk around the wall. As such, no test is required. But if the hero were being chased by enemies, failing to leap over the wall means the pursuers can catch them, so the

Director might decide to call for a test to determine what happens.

So, in our Pirate Borg game, when a character wants to throw a grappling hook to climb, we should first ask whether this even merits a check!

If there is nothing dramatic, then no check is needed or should be called for. Let’s take a step back in time and consider possibilities:

• The characters are exploring an island and want to climb to look around.
• The characters are being chased by a zombie horde, and need to climb to safety.
• The characters are climbing to get in front of their enemy and set up an ambush.

When we consider it this way, we can see that each situation has different gameplay implications. In the first, there are no obvious consequences. If we don’t know, we can ask the player. Why are you climbing? If it is to determine where to go next, we then as GM can make a decision of whether this should simply work. The PC gazing over the landscape and seeing some options for where to go could actually make the adventure more interesting. Or maybe we know there are some details that, seeing them, would provide something extra. We might call for a check to see how many of the details they see. Or, if the characters are survivors of a shipwreck and we want to lean into survival, maybe the check isn’t to climb but instead to see if you fashion a grappling hook from driftwood and woven fibers. Failure means you need to find better materials somewhere else, then return to the cliff.

In the second situation, we have clear stakes from an approaching zombie horde. While it is possible to keep trying with the grappling hook, each failure might mean a couple of zombies might reach the party and attack! Each attempt would carry a ton of excitement.

In the third situation, climbing with no failure might allow everyone to get ahead of their enemies and the ambush is set up in time. A single failure might mean they get there just ahead of the approaching enemies and this might have a consequence or make the ambush easier to spot. More than one failure might mean they arrive too late, and no ambush can be set up.

Failure and Gating

When we consider what failure represents, we want to be wary of gating progress. The simplest example is… a gate! We have a locked gate or door and it leads to somewhere important. We logically think it would have a lock to prevent access. But if the characters fail to pick the lock, now no progress is possible. A surprising number of official adventures from many different RPG companies have this kind of situation.

We can simply not place a lock, which removes this problem. However, it also removes anything of interest.

Another option is to place the lock, but to also provide for consequences. Failing to pick the lock, the heroes can bash it down. No check is required, but time is spent and everyone near the door knows the heroes are coming. Or, perhaps a failure to pick the lock means they must now try to pick the pocket of the guard outside, with a chance they are discovered. The point is, we added consequences rather than gating progress.

Thinking about failure is important when we design scenarios. In the Pirate Borg scenario where they are climbing up to escape zombies… what if they roll poorly many times? We may want to decide that after a certain number of failures, they simply succeed because at that time they have taken severe damage. Or, maybe they can always choose to abandon the cliff and jump into the water, which will force them to end up in a different place than they wanted to be, perhaps with other dangers.

Is Success Possible?

Just as we don’t want to call for a roll when success will eventually happen, we also don’t want to call for a check when success is impossible. If the cliff can’t be climbed, because it is made of crumbling dirt, then we want to state that up front. And, to acknowledge that this is a barrier, so there must be another way to get around it.

Degrees of Success and Failure

An alternative is to have degrees of success or failure. Maybe succeeding on the first try means you can get up before the zombies. Succeeding after one to two rounds might mean each character is attacked once. Succeeding after three rounds… you get the picture.

When we ponder these kinds of scenes, we want to think through the gameplay. Maybe each failure reduces HPs, as they get banged up. Or maybe it’s more zombie attacks. Or maybe this should be a skill challenge and the grappling hook is one of several checks. Failing one doesn’t end progress, but if there are x failures before y successes, some drawback takes place.

MCDM has a very cool system for Montages and 4E had Skill Challenges to handle scenarios like this, but these aren’t the only options.

Multiple Checks for Success?

One final caution. Beware creating situations where you string together several checks.

I recall a game I watched once where the character was trying to climb a cliff, so they could look for landmarks. The DM called for a climb check every ten feet. They needed to roll something like a 10 or higher to succeed… but doing that three times in a row? They failed on the third check, falling and dying. That’s not fun, because you doomed the character and there was nothing interesting. The bad odds didn’t match the stakes.

A better way to handle this is single roll and establish a height up front where the check takes place (with risk matching reward and stakes).

Or, use degrees of success. Maybe there are three rolls, but failure represents the cuts and bruises you take on the way up. You won’t fall. The question is how good you look when you get there. This is the concept behind Draw Steel’s tiers of success on skill tests. It’s also where many RPGs introduce concepts like succeeding with a complication and failing with an advantage. We might say that if you fail all three rolls you get banged up but give an advantage to someone else to try. One success means some damage but you reach the top. Two successes means no damage and you reach the top. Three successes means no damage, reach the top, and everyone who follows you only needs to make two checks.

Next time, we look at multiple PCs trying to help with one skill check!