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Alright so I've heard talk of specific rules overruling generic rules, but both of these seem like specific rules to me.

So the Halfling racial trait Lucky (which I'll call Halfling Luck from here on out, to help avoid confusion) states:

When you roll a 1 on an attack roll, ability check, or saving throw, you can reroll the die and must use the new roll. (PHB, 28)

and the Lucky feat specifies:

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 choose which of the d20s is used for the attack roll, ability check, or saving throw. (PHB, 167)

Meaning that if you use a point with an advantage or disadvantage roll, you're allowed to choose from any of the three rolls.

So if you use Halfling Luck to reroll a 1, can you then decide to use a luck point and still get to choose any of the dice? Or if you use a luck point and that dice rolls a 1, do you reroll it with Halfling Luck and then still get to choose any?

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I think this is pretty cut and dried with just what you have quoted. If you're a Luck Halfling and you roll a 1, you can re-roll it once and use the number. Then if you just don't like any number you rolled, even the re-roll, you can spend a luck point to re-roll (again). One doesn't replace the other, you simply have both features, and both operate exactly as they written.

First Case: Feature then Feat

So if you use Halfling Luck to reroll a 1, can you then decide to use a luck point and still get to choose any of the dice?

Yes.

Example

Let's say you roll to attack, and roll a natural 1. Your halfling luck kicks in:

When you roll a 1 on an attack roll, ability check, or saving throw, you can reroll the die and must use the new roll. (PHB, 28)

You get a, say 5. It still isn't high, so you choose to use your luck feat.

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 choose which of the d20s is used for the attack roll, ability check, or saving throw. (PHB, 167)

Second Case: Feat then Feature

Or if you use a luck point and that dice rolls a 1, do you reroll it with Halfling Luck and then still get to choose any?

Not quite. The roll is whichever you choose when you use in the feat Lucky. So, you could choose the 1, and then get to re-roll, as per RAW, but you'd have to use the number of that Halfling luck reroll not the previous two.

Example

So, in this case you roll a 3 and use Luck Feat to roll again, you roll a 1.

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 choose which of the d20s is used for the attack roll, ability check, or saving throw. (PHB, 167)

You choose the 1, specifically to trigger your halfling ability. So, you've now effectively rolled a 1, and get to reroll it:

When you roll a 1 on an attack roll, ability check, or saving throw, you can reroll the die and must use the new roll. (PHB, 28)

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    \$\begingroup\$ Well technically the Lucky feat doesn't have you re-roll one of the dice, it has you roll a completely new dice and sort of "add it to the pot" of dice rolls and choose from any of them. But I get what you mean about basically whichever one I use last is the one who's rules I follow. \$\endgroup\$ – J Nason Oct 8 '16 at 4:38
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    \$\begingroup\$ This is how the Lucky Feat actually works. dnd.wizards.com/articles/features/sageadvice_feats \$\endgroup\$ – Airatome Oct 8 '16 at 13:47
  • \$\begingroup\$ @JNason is correct. The feat adds a die to the pool, including turning disadvantage into "super advantage" (see the sage advice). Halfling racial trait re-rolls the die. \$\endgroup\$ – Mindwin Sep 12 '17 at 17:16
  • \$\begingroup\$ Mindwin, That is true of the Lucky Feat, not of halfling luck. In the case of disadvantage you roll the disadvantage and then use the luck feat to choose which of the three to use -- which is how the first instance works. However, in the second instance they use luck and choose to use the 1 to trigger the Halfling luck, which then rerolls that 1 into whatever comes up on that die -- it isn't a "super advantage" situation like disadvantage or the first case is... Following RAW. \$\endgroup\$ – J. A. Streich Sep 12 '17 at 19:55
  • \$\begingroup\$ I believe the OP's confusion came from the Halfling's Lucky trait including the phrase "[you] must use the new roll". Why do think that the Lucky feat overrules this clause in the Halfling trait? \$\endgroup\$ – Medix2 Aug 14 at 10:46
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When you roll a 1 on an attack roll, ability check, or saving throw, you can reroll the die and must use the new roll.

If you use the lucky trait to re-roll the one, the rule specifically says you must use the new roll. You could still roll the for the lucky feat, but you can't use that roll.

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Here's another possible interpretation: Say you use 1 or more luck points, and you're rolling 3 d20's to make a check For each of those d20's, if you roll a 1, you re-roll it if you're a Halfling

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    \$\begingroup\$ Hi @derelbenkoenig, welcome to RPG.SE! I encourage you to take the tour; it's a useful introduction to the site. We work a little differently than some other sites; in particular, answers with specific justification in the text, or experience at how a ruling works out in play, are favored over those that only give possible interpretations. I don't think your idea is bad, but do you have a particular reason for going that way? Also, can you explain the implications in a little more detail? For example, when would one have to make the decision to use either or both traits? \$\endgroup\$ – SirTechSpec Sep 11 '17 at 22:48
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    \$\begingroup\$ You cannot use more than one luck point at a time. Advantage and disadvantage (and the lucky feat) don't allow a halfling to reroll multiple dice. Only one dice may be rerolled. \$\endgroup\$ – Johnathan Gross Sep 12 '17 at 6:08

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