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If I have the Lucky feat, 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?

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According to this Sage Advice column, 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. It does still preclude using things dependent on not having disadvantage (like Sneak Attack). You can even choose to roll the third die after you've seen the result of the roll.

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As noted in xanderh's answer, the way Lucky interacts with disadvantage (RAW) is:

  1. You roll 3 die.
  2. You choose which one you want to use.

This effectively turns disadvantage into a huge advantage, except for the fact your action is still treated as done in disadvantage, as noted here. So, answering your question, no, you don't get to not expend the lucky dice, but you also can't ever get a worse outcome, because you still can choose the higher dice from before.

However the reason I am necro'ing this thread is because I'd like to add some references from Crawford.

First, it should be noted that in what seems to be the first time this question came to surface, the answer was actually different. In this answer, you would take the middle dice (second best/second worst). This might indicate that RAI, originally, Lucky shouldn't be so good. It is also stated as a potential problem and other solutions have been proposed. I'd like to remark the

Sage advice is for clarification, not redesign.

and

In Sage Advice, I explain how the game works, not how I wish it worked.

With that in mind, as a player you should probably ask your DM how he's going to handle this interaction before choosing the feat, and as a DM it's up to you choosing between RAW and (possibly) RAI (certainly more balanced). Unlike RAW, as a DM you can play exactly how you wish it was played and how you think it should be played.

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    \$\begingroup\$ Worthy answer. I usually go RAW, but knowing that Crawford regards the RAW as problematic makes me want to rule the less lucky way. \$\endgroup\$ – keithcurtis Apr 15 '18 at 17:33
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    \$\begingroup\$ @Hellsaint FYI I updated the top line of your answer to correctly attribute that post to xanderh. Thomas Nyman didn't write it, they just edited it. \$\endgroup\$ – doppelgreener♦ Apr 15 '18 at 18:01
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It's simpler than that. A disadvantage roll rolls 2d20 and discards the higher one, leaving only the lower; once you know what number your single one die has rolled, you can choose to spend a Luck Point to roll a second 1d20 (this one without the disad) and then choose which of the two rolls you take.

TL;DR You don't choose among three dice, you choose between two rolls.

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    \$\begingroup\$ This almost directly contradicts the previous post. While yes this might be an interpretation of the rules, the previous post contains info from an authority on the Rules as Written. \$\endgroup\$ – Ben Sep 27 '15 at 6:19
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    \$\begingroup\$ The feat also says "regardless of how many dice are involved" \$\endgroup\$ – daze413 Sep 27 '15 at 11:00
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    \$\begingroup\$ This is my interpretation of the feat as well. I don't actually understand how Sage Advice comes up with their interpretation. \$\endgroup\$ – Greenstone Walker Dec 4 '17 at 1:26
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    \$\begingroup\$ While this is the most reasonable interpretation, the timing language of Lucky means this is not RAW. "Whenever you [make a roll], you can ... roll an additional d20. ... You choose which of the d20s is used...". You may also choose to spend the luck point "after you roll" but before an "outcome is determined". So it does, both RAW/RAI, grant super advantage from disadvantage. But as the GM, your decisions are final! This is a great example of why playing solely by the RAW or RAI can cause silliness in the game. Use your judgement to make rulings that are right for your table! \$\endgroup\$ – Aaron3468 Jan 19 at 20:04
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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.

I don't know why Crawford would interpret the text that way, and I hope that if it is addressed in an official Errata, he will reconsider what he said (assuming he said it on Twitter). I think that El Suscriptor is correct.

For one, you do expend a luck point if you roll a luck die because "you can spend one luck point to roll an additional d20" whenever you make an attack, meaning that if you choose to use your luck point and roll, it will be expended. This is indicated by the phrase, "You can choose to spend one of your luck points after you roll the die, but before the outcome is determined," which isn't commenting on when you can choose to expend a luck point in and of itself. Rather, it refers to the time that you may expend your luck point as part of the mechanism that it entails. In other words, expending a luck point necessarily gives you the right to roll a die to give you the de facto advantage.

Two, the text unambiguously states that there is no "superadvantage." This is because die is singular, not plural:

You can choose to spend one of your luck points after you roll the die, but before the outcome is determined.

It's saying, "You can spend a luck point [and therefore roll another die] after your attack roll [of one die]." If there were a "superadvantage," the previous sentence would say "die or dice," but it does not. This means that, as El Suscriptor said, you choose between two rolls. It is like doing the order of operations in a simple math equation. For example, if you look at 2*(5+3), you don't multiply 5 by 2 and then 3 by 2, you need to conclude the addition within the paraphrase. Using that same order of logic, you need to conclude the advantage or disadvantage procedure.* If you roll a 1 and a 20 with disadvantage, you take the 1. That is your die after the roll, and then a luck point can be expended (roll a die) before the outcome is determined (i.e. when the DM says you crit missed or whatever).

* Procedure:

When you have either advantage or disadvantage, you roll a second d20 when you make the roll. Use the higher of the two rolls if you have advantage, and use the lower roll if you have disadvantage. For example, if you have disadvantage and roll a 17 and a 5, you use the 5. If you instead have advantage and roll those numbers, you use the 17.

Notice that you must decide which of the two dice must be used. It must be concluded, and it's mutually exclusive of any other rolls or procedures. It is a bracketed section of a math equation.

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    \$\begingroup\$ Your argument seems to hinge on the authors eschewing the phrase "die or dice." But there are literally hundreds of occurrences of "die" which would have to be replaced with "die or dice" if your reading is correct. (Or, if we don't, then it turns out that (dis)advantage doesn't come into play nearly as consistently as we thought.) Can you address the precedent your reading would set? \$\endgroup\$ – nitsua60♦ Apr 18 '16 at 19:50
  • \$\begingroup\$ I wanted to upvote this just because I think it brings some value... oh hell I did upvote, but nearly didn't because of " 2*(5+3), you don't multiply 5 by 2 and then 3 by 2"; this is wrong. The correct statement is "you don't multiply 5 by 2 and then add 3", since algebra (factoring) certainly relies on the distributive property! Any ways back to your idea about sets. We interpret it the same way. Adv and disadvantage are considered a single roll. We frequently use lucky and no one to date has has thought to use it in this way... \$\endgroup\$ – Quaternion Nov 11 '18 at 20:16
  • \$\begingroup\$ @nitsua60 you are right in that his argument is about the plurality. We are not concerned about all the places die could replace dice, only those places where a d20 is concerned with advantage and disadvantage. His argument is that advantage and disadvantage are sets (of two) with pick highest and pick lowest respectively, this results in a single die outcome. I think this is clear. In this interpretation there is a significant difference between spending the luck point up front (at the time of the roll which would result in a set of 3 pick highest) and after which results in this outcome. \$\endgroup\$ – Quaternion Nov 11 '18 at 20:31
  • \$\begingroup\$ Run disadvantage procedure, including picking the lower roll. All is good. Now use Lucky. It states you can choose which die to use, which makes the disadvantage pick irrelevant; you could even pick the higher of the two original disadvantage dice. Still, good analysis: +1 \$\endgroup\$ – Yakk Dec 6 '18 at 19:56

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