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For example, a halfling has advantage on an attack and rolls an 8 and a 1. The 8 misses. Does he get to re-roll the 1 using Luck?

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Yes, the halfling gets to reroll the 1. (The halfling gets to reroll the 1 even if the 8 didn't miss.)

How abilities that allow rerolls — like the hafling Lucky trait — apply to advantage and disadvantage is not immediately obvious, so it's actually covered explicitly in the rules for advantage and disadvantage, even using Lucky as the example (PHB, p. 173; Player's Basic Rules, p. 57):

When you have advantage or disadvantage and something in the game, such as the halfling’s Lucky trait, lets you reroll the d20, you can reroll only one of the dice. You choose which one. For example, if a halfling has advantage on an ability check and rolls a 1 and a 13, the halfling could use the Lucky trait to reroll the 1.

So yes, you get to reroll the 1. If both dice came up 1 though, you'd only reroll one of them though, not both.

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  • \$\begingroup\$ Can you please cite us a rule that says that when rolling two Natural 1s on an action, you get to re-roll only a single one? As per RAW it seems each and every Natural 1 gets rerolled, and for that Natural 1 you accept the new roll, end of story. \$\endgroup\$ – Pat Nov 26 '20 at 20:21
  • \$\begingroup\$ @Pat Is the quote in the answer not already "a rule that says that when rolling two natural 1s… you get to re-roll only a single one". The quoted rule says, "When you have advantage or disadvantage and something in the game… lets you reroll the d20, you can reroll only one of the dice." Am I misunderstanding your question? \$\endgroup\$ – SevenSidedDie Dec 4 '20 at 17:53

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