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Ok so here is the rule:

Lucky
You have inexplicable luck that seems to kick in at just the right moment. You have 3 luck points. 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 the rule only states "you can spend one luck point to roll an additional d20", and then says "you can spend one luck point after you roll the die".

So my question is a bit of a two-parter:

  1. If I don't like the roll I made on my luck die, (Eg. I roll a 10, choose to roll a luck die, then rolled a 5) do I not have to spend the luck point?
  2. Can I spend more than 1 luck point per roll? Eg. I roll a 10, choose to roll a luck die and rolled a 5 - can I roll another luck die?
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    \$\begingroup\$ Related discussions of the Lucky Feat and Luck Rolls are here and also here. \$\endgroup\$ – KorvinStarmast Oct 29 '15 at 12:43
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  1. "...you can spend one luck point to roll an additional d20...". In order to roll the additional d20, you spend the luck point. Cause and effect. Very similar to "you open the door to get through" - you don't go through the door first and then decide if you want to open the door. ;)

  2. "Whenever you make an attack roll, an ability check, or a saving throw, you can spend one luck point...". The die roll granted by Lucky is not any of these rolls - it is a re-roll of the triggering roll, and is thus not treated as a separate roll. Using the venacular of damage rules, it is an "untyped" roll. And because you've already burned a luck point on the triggering roll, you can't burn more because the rules restrict you to just one luck point per triggering roll.

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  1. The luck point "buys" you the extra roll. IE, it's spent before the luck roll. Once you have rolled the additional die,

    You choose which of the d20s is used for the attack roll, ability check, or saving throw.

  2. You can spend one luck point...

    Whenever you make an attack roll, an ability check, or a saving throw, you can spend one luck point to roll an additional d20.

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By RAW, you can use them once per attack roll, ability check or saving throw.

This is actually covered in the wording of the ability, wherein it states (emphasis on the important bit):

Whenever you make an attack roll, an ability check, or a saving throw, you can spend one luck point to roll an additional d20.

The luck die isn't an attack roll, ability check or saving throw, so it would not trigger an additional luck roll option.

If you don't like the roll, you're unfortunately stuck with it. You spend the point to make the roll before the outcome is determined, but rolling the luck die still costs you a luck point.

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I think your confusion is caused by misparsing the language of the rule.

Specifically, "the die" in the phrase "after you roll the die" does not, as you seem to have assumed, refer to the "additional d20" mentioned at the end of the previous sentence, but to "an attack roll, an ability check, or a saving throw" mentioned earlier.

Read that way, the sequence of events is clear:

  • You decide / need to make an attack roll, an ability check, or a saving throw:

    • You roll a d20 to determine the outcome.

    • After rolling the die, but before the outcome is determined, you may decide to spend a luck point:

      • If you do, you get to roll another d20, and choose which one of the rolls is used.
    • The outcome of the attack roll, ability check or saving throw is then determined according to the result of the (chosen) d20 roll.

Your original reading, with "the die" referring to the "additional d20", on the other hand, would produce a nonsensical and self-contradictory result: you need to spend a luck point in order to roll the additional d20 in the first place, so you cannot decide whether or not to spend the point after you've rolled it — by then, that decision has already been made. As Pitzy writes in their answer, that would be like deciding whether or not to open a door after having already walked through it.

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I wouldn't over-think this. You can spend 1 luck point to make your check with advantage. The only detail is that you can choose to spend the point AFTER the initial roll, but before you know the outcome. Making an attack roll? You get a 5 and your pretty sure (but not completely certain) that's a miss, so you spend a luck point, roll again, and choose which die to use for your final result. That's it.

EDIT: Per comments below, my response doesn't mean to imply that you actually HAVE advantage on the check, I was attempting to convey the similarity. You wouldn't get the benefit of special class abilities, like Sneak Attack, or other features because of Lucky, you just get the extra die roll.

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    \$\begingroup\$ Note that the lucky die does not grant advantage. You will not trigger sneak attack or any other effect relying on advantage by using the "lucky" feature! \$\endgroup\$ – Neuneck Oct 29 '15 at 12:52
  • \$\begingroup\$ Agreed. I was attempting to convey that the idea behind Lucky shouldn't be over complicated. \$\endgroup\$ – Red Wullf Oct 29 '15 at 14:16

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