The Halfling Racial feature Lucky reads as follows:
Lucky When you roll a 1 on the d20 for an attack roll, ability check, or saving throw, you can reroll the die and must use the new roll.
So there are two very important words here, "Can" and "Must".
When rolling with disadvantage, if one of the two dice is a 1 you Can re-roll it, and you Must use the new roll. This seems to indicate that regardless of whether the new roll is the lesser of the two (from disadvantage) it is the result.
The rules and even tweets from Crawford on the subject only seem to focus on the rare instance when you might get double 1s. And further don't actually clarify if a double 1 with disadvantage can be negated by a Halfling's luck. They only clarify that you can only re-roll once for the attack, save, or check.
Further, when rolling with advantage, if one of the two dice is a 1 you Can re-roll it, and you Must use the new roll. Meaning if you roll a one and, lets say, an 18. If you choose to re-roll the 1 and get a 4 you Must use the 4, not the 18.
This interpretation leads to more speculation and meta game thinking when it comes to decisions about using the feature when you have advantage. This is really counter to the feel of 5th edition, and likely is not the intent.
Would you play this feature as written or allow your players to do so?
The rules as written are vague, since the phrase "use a roll" is not actually defined. Use it for what? One could argue that it means you reroll a dice and then must use the new roll as the result of the old roll, i.e. that you cannot choose to use the old value or reroll again via any method. The implication of that interpretation would be that this does not override the mechanism of advantage or disadvantage, in that having rerolled one dice and been forced to replace its value you must now select which of those two dice rolls to use for the result of the check as normal. I feel that this interpretation is perfectly valid, and that it fits best thematically given that a halfling's lock should really be an inherent trait, but something that should involve strategically calculating whether using a reroll has a minor chance of making things better or worse. Blanket rule becomes: halfling rolls some d20, a 1 is visible, a single 1 is rerolled, then calculate result as normal.
Advantage: 12,1 (reroll) -> 12,7 = 12 (result)
Disadvantage: 12,1 (reroll) -> 12,7 = 7 (result)
Someone might produce a twitter ruling or argue that this or that phrase has been defined, but I think I have no intention of listening to arguments that are trying to make the mechanics of the game stupider or more counterintuitive.
This seems to be the way it is usually treated, and the simplest interpretation to implement, but who can pass up a nearly 10% chance to completely negate disadvantage. It's the D&D equivalent to the Monty Hall problem.
The RAI is to prevent players from ever rerolling a reroll, not to make the feature a metagaming headache. The new roll stands; but advantage/disadvantage rules still mean you take the highest or lowest of the two final rolls. The only reason you should ever choose not to reroll a 1 is if you think it is narratively preferable to fail at the task. Any other interpretation of Lucky is, pardon, asinine.
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The Halfling Racial feature Lucky reads as follows:
Lucky
When you roll a 1 on the d20 for an attack roll, ability check, or saving throw, you can reroll the die and must use the new roll.
So there are two very important words here, "Can" and "Must".
When rolling with disadvantage, if one of the two dice is a 1 you Can re-roll it, and you Must use the new roll. This seems to indicate that regardless of whether the new roll is the lesser of the two (from disadvantage) it is the result.
The rules and even tweets from Crawford on the subject only seem to focus on the rare instance when you might get double 1s. And further don't actually clarify if a double 1 with disadvantage can be negated by a Halfling's luck. They only clarify that you can only re-roll once for the attack, save, or check.
Further, when rolling with advantage, if one of the two dice is a 1 you Can re-roll it, and you Must use the new roll. Meaning if you roll a one and, lets say, an 18. If you choose to re-roll the 1 and get a 4 you Must use the 4, not the 18.
This interpretation leads to more speculation and meta game thinking when it comes to decisions about using the feature when you have advantage. This is really counter to the feel of 5th edition, and likely is not the intent.
Would you play this feature as written or allow your players to do so?
Extended Signature
The rules as written are vague, since the phrase "use a roll" is not actually defined. Use it for what? One could argue that it means you reroll a dice and then must use the new roll as the result of the old roll, i.e. that you cannot choose to use the old value or reroll again via any method. The implication of that interpretation would be that this does not override the mechanism of advantage or disadvantage, in that having rerolled one dice and been forced to replace its value you must now select which of those two dice rolls to use for the result of the check as normal. I feel that this interpretation is perfectly valid, and that it fits best thematically given that a halfling's lock should really be an inherent trait, but something that should involve strategically calculating whether using a reroll has a minor chance of making things better or worse. Blanket rule becomes: halfling rolls some d20, a 1 is visible, a single 1 is rerolled, then calculate result as normal.
Advantage: 12,1 (reroll) -> 12,7 = 12 (result)
Disadvantage: 12,1 (reroll) -> 12,7 = 7 (result)
Someone might produce a twitter ruling or argue that this or that phrase has been defined, but I think I have no intention of listening to arguments that are trying to make the mechanics of the game stupider or more counterintuitive.
This seems to be the way it is usually treated, and the simplest interpretation to implement, but who can pass up a nearly 10% chance to completely negate disadvantage. It's the D&D equivalent to the Monty Hall problem.
Extended Signature
The RAI is to prevent players from ever rerolling a reroll, not to make the feature a metagaming headache. The new roll stands; but advantage/disadvantage rules still mean you take the highest or lowest of the two final rolls. The only reason you should ever choose not to reroll a 1 is if you think it is narratively preferable to fail at the task. Any other interpretation of Lucky is, pardon, asinine.
Even a blind squirrel finds a nut once in awhile.