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I've been reading through RAW, and I simply cannot find an answer to this question. My apologies if it is stated somewhere and I'm just missing the obvious.

Once Inspiration has been granted, when exactly can it be used by a PC? Is it only before the original roll is made, or can it be spent after a failed roll to essentially grant a re-roll?

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From the Player's Basic Rules v 0.2, page 35:

Using Inspiration

If you have inspiration, you can expend it when you make an attack roll, saving throw, or ability check. Spending your inspiration gives you advantage on that roll.

Generally, if something lets you wait until after the roll and see how you did before you use it, it specifies that. "When you make" a roll suggests that you use it at the same time as the roll, which isn't that helpful, but its effect is to give you advantage, which says (page 57):

Advantage and Disadvantage

Sometimes a special ability or spell tells you that you have advantage or disadvantage on an ability check, a saving throw, or an attack roll. When that happens, you roll a second d20 when you make the roll.

This is more helpful, because it says you roll the second d20 when you make the roll. So advantage doesn't allow you to make the roll, then use your second d20; you roll them both at the same time. Since inspiration just gives advantage, it seems clear that you have to decide to use it before you roll.

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    \$\begingroup\$ Although I agree with your conclusion, I find the evidence provided here confusing. You're using "when you make the roll" (2nd text) to support your conclusion of what "when you make an attack roll, saving throw, or ability check" means. If we're unsure what the first meant, then I'm not sure how the second helps us. Both timings are "when you make [a]... roll." \$\endgroup\$ – Gandalfmeansme Oct 30 '18 at 16:44
  • \$\begingroup\$ This is particularly problematic because "when you roll" is sometimes used in contexts that clearly are to be used when a roll has already been made (such as a the sorcerer's Empowered Spell metamagic). \$\endgroup\$ – Gandalfmeansme Oct 30 '18 at 16:54

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