“Next time for sure!”

One of the aspects of the Dungeons & Dragons rules that is somewhat missing is a discussion of whether or not you can reroll an ability (skill) check.

This is something that various editions of D&D have treated differently. In first edition, the rule was generally no. In third edition, it was generally yes – with a few exceptions.

So, which version should you use? Honestly, it depends on the situation.

Two Questions

Making an ability (skill) check tends to be trying to answer one of two questions:

• Are you talented enough to succeed at this task?
• How long does it take you?

If you are allowing rerolls, you are asking the second question. If you are not allowing rerolls, you are asking the first.

Allowing Rerolls

In the dungeon exploration of early D&D, stuck doors were a standard feature, opened on a roll of 1 on 2 on d6 (for standard strength characters). There was never any question that the door would open, but the question was “how long?” Why did this matter? It mattered because failing on that first check negated surprise and permitted one more time for the opponents to prepare or call for reinforcements.

Obviously, if there is no time pressure, then allowing rerolls is rather pointless. You might as well just allow the player to succeed on the first attempt. Third edition has a “Take 20” mechanic which assumed that the player would try until they succeeded – and standardised it as taking 20 times as long. As a mechanic, it was a way of getting away from making rerolls, but it was asking the wrong question. Taking 20 assumes time does not matter. Instead, it is asking if the character is good enough.

As an alternative to time pressure, perhaps there are other consequences on a failed roll. Disarming traps and climbing have been classic examples. If you fail the check by 5, the trap goes off or you fall and take damage. That makes each individual roll interesting – and that is what you want.

Not Allowing Rerolls

When you only allow a character to try once, you are letting the dice decide if they are good enough. And, honestly, I am fine with that.

Some typical rolls that I like to keep the “roll once” on are Opening locks and using knowledge skills like Nature and Arcana. Either you know a thing, or you do not.

One aspect of not allowing rerolls is that the DC of the checks need to be relatively low so that skilled characters feel accomplished. Constantly failing checks for skills that you are trained in is not that great.

Never, ever put a no-reroll check on a check that the party needs to succeed to continue the adventure. The best solution is to have alternative routes to success, so that this failed check does not derail the adventure and the characters can try something else.

Sometimes Allowing Rerolls

Even in games where rerolls are typically not allowed, we allow rerolls when the situation changes.

For instance, in AD&D, you can try Open Locks again when your skill gets better – such as from gaining a level.

Some games (like Cyberpunk RED) allow a reroll if you change the conditions, so you get a bonus on your original roll.

Variants of Training

A couple of variants for ability (skill) checks I like to use:

• Characters with Expertise or Proficiency (you can choose the level) automatically succeed, everyone else has to roll
• Only characters with Expertise or Proficiency can roll. No-one else can try.

These can be particularly useful for limiting knowledge checks.

You must be “This High”

The one aspect of Take 20 I do not like? When it says to a player, “Your character needs a +10 in this skill to succeed”. Because that is what it often means.

I like it when there is more of a variance to the questions that we ask the game. And it is why setting the DCs to be achievable is so important!

Take 20 worked a little better in 3E because there was the possibility of varying how much you had invested in a skill (skill points); but in 5E, there is not enough of a variance to make that an interesting question.