[RPG] How is the “Lucky” Feat affected by Advantage/Disadvantage


If I have the Lucky feat1, it allows me to choose to take a re-roll, to see if I might do better on a d20 check:

Whenever you make an attack
roll, an ability check, or a saving throw, you can spend
one luck point to roll an additional d20. You can choose
to spend one of your luck points after you roll the die,
but before the outcome is determined.
You choose which
of the d20s is used for the attack roll, ability check, or
saving throw.

So in the chance of a disadvantaged roll, I can choose to attempt a better roll; but if the outcome is still worse, it does not expend a "luck point", should I choose. Is this the case?

1 Not to be confused with the Halfling's racial trait also called Lucky that works somewhat differently.

Best Answer

According to this question from the Sage Advice Compendium, if you roll with disadvantage and use a luck point, you get to choose which of the three dice you use, effectively turning disadvantage into super-advantage:

How does the Lucky feat interact with advantage and disadvantage?

The Lucky feat represents extraordinary luck that can help you when you need it most. It lets you spend a luck point; roll an extra d20 for an attack roll, ability check, or saving throw; and then choose which d20 to use. This is true no matter how many d20s are in the mix. For example, if you have advantage or disadvantage on your attack roll, you could spend a luck point, roll a third d20, and then decide which of the three dice to use. You still have advantage or disadvantage, since the feat doesn’t say it negates it, but you get to pick the die. The upshot of this fact is that a rogue, for instance, who has disadvantage on an attack roll couldn’t use Sneak Attack even if the rogue uses the Lucky feat to pick the die.

The Lucky feat is a great example of an exception to a general rule. The general rule in this case is the one that tells us how advantage and disadvantage work. The specific rule is the Lucky feat, and we know that a specific rule trumps a general rule if they conflict with each other.

If a DM wants advantage and disadvantage to play their normal roles even when the Lucky feat is used, here’s a way to do so: roll two d20s for advantage/disadvantage, roll a third d20 for Lucky, eliminate one of the three dice, and then use the higher (for advantage) or lower (for disadvantage) of the two dice that remain.

It does still preclude using things dependent on not having disadvantage, like Sneak Attack, which Jeremy Crawford reminds us of in this tweet. You can even choose to roll the third die after you've seen the result of the roll.