How do the Drunken Master monk's Drunkard's Luck feature and the Great Old One warlock's Entropic Ward feature interact?

Question

The Way of the Drunken Master Monk gets the Drunkard's Luck feature, which states:

When you make an ability check, an attack roll, or a saving throw and have disadvantage, you can spend 2 ki points to cancel the disadvantage for that roll.

The Great Old One warlock's Entropic Ward feature states:

[...] When a creature makes an attack roll against you, you can use your reaction to impose disadvantage on that roll [...]

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Both of these happen "when a creature makes an attack roll", though Entropic Ward requires a reaction, which might be relevant. I'm confused as to the timing of these events, though Xanathar's Guide to Everything does have this section on "Simultaneous Effects" (p. 77):

If two or more things happen at the same time on a character or monster’s turn, the person at the game table — whether player or DM — who controls that creature decides the order in which those things happen. For example, if two effects occur at the end of a player character’s turn, the player decides which of the two effects happens first.

We also know that both of these features occur before the roll. This is intuitive, as it would be weird to give somebody disadvantage after they rolled (what would even happen if you already rolled with advantage and somebody then gave you disadvantage?). We also know this because there are features which explicitly say they can be used after a roll (such as the Bard's Cutting Words), which these features do not:

When a creature that you can see within 60 feet of you makes an attack roll [...] you can use your reaction to expend one of your uses of Bardic Inspiration [...] You can choose to use this feature after the creature makes its roll, but before the DM determines whether the attack roll or ability check succeeds or fails [...]

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So what happens when a Drunken Master monk attacks a Great Old One warlock and the Warlock uses Entropic Ward - can the Monk then use Drunkard's Luck?

What happens if the Monk has disadvantage and attacks the Warlock - does Drunkard's Luck apply first and remove the regular disadvantage, but then Entropic Ward adds a new instance that isn't removed? Does Entropic Ward apply first, and then Drunkard's Luck removes both instances/causes of disadvantage?

Answer 1

The monk can negate the disadvantage after it is applied.

The rules for making an attack are given in the Player's Handbook on page 193:

Whether you're striking with a melee weapon, firing a weapon at range, or making an attack roll as part of a spell, an attack has a simple structure.

1. Choose a target. Pick a target within your attack's range: a creature, an object, or a location.

2. Determine modifiers. The DM determines whether the target has cover and whether you have advantage or disadvantage against the target. In addition, spells, special abilities, and other effects can apply penalties or bonuses to your attack roll.

3. Resolve the attack. You make the attack roll. On a hit, you roll damage, unless the particular attack has rules that specify otherwise. Some attacks cause special effects in addition to or instead of damage.

If there's ever any question whether something you're doing counts as an attack, the rule is simple: if you're making an attack roll, you're making an attack.

Notice that all modifiers are determined before making the attack. The "resolve the attack" step where it says "You make the attack roll." occurs after the step of "determining modifiers."

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I feel it is appropriate to add one last thing: the original post pointed out the bard's feature that allows an attack modifier to be added after the attack roll is made, this is permissable under the 'specific beats general' rule in the PHB on page 7

If a specific rule contradicts a general rule, the specific rules wins.

It can possibly be argued that the warlock's feature conflicting with the monk's feature is a special rule. That the disadvantage the warlock gives is when the attack roll is made which is under 'resolve the attack.' To that I would argue this from the rules on making an attack: it says, "when you're making an attack roll, you're making an attack." These three steps are the steps that you take when making an attack, as such, when you do something to 'make an attack roll' you are actually beginning the three step process, any changes that are made 'when you make an attack roll' are made at the appropriate time within this three step process.

Answer 2

If they actually happen simultaneously, it is up to whoever's turn it is.

As you pointed out, it might not necessarily be the monk's turn. Generally this interaction would probably be happening on either the monk or warlock's turn, so I imagine it would generally resolve to that player's favor.

You also linked the answer about whether reactions interrupt their triggers. Because Entropic Ward is worded to occur WHEN a creature makes an attack roll, I would argue this is both the trigger and the timing, and this reaction should interrupt the trigger.

Furthermore, the Drunkard's Luck ability is not a reaction, so it's only limitation, as far as I can tell, is that you have 2 ki points to spend, and you are making a roll with disadvantage. With that in mind, in your second scenario, I would go as far as to say the monk could clear a previous disadvantage from the roll, the warlock could re-apply disadvantage through Entropic Ward, and then the monk could spend two more ki points to clear it again. This all happens sequentially "during" the roll.

HOWEVER, let's make the argument that it doesn't interrupt the trigger and they don't happen simultaneously.

You mention also that intuitively, it wouldn't make sense for Entropic Ward to impose disadvantage after the roll, however, I can't find any rules that explicitly state both d20 must be rolled simultaneously for disadvantage, simply that you roll two and take the lower. So even if we go with the interpretation that disadvantage is applied after the initial trigger we could still do so between the initial roll and resolving the attack. The sequence of the events would be something like:

1. Monk makes initial attack roll
2. WHILE that is happening, warlock declares that they are using their reaction for Entropic Ward.
3. Monk's initial roll completes, Entropic Ward activates
4. Monk must now roll a second time to apply the disadvantage
5. Monk instead spends 2 ki points and uses the first roll.
6. Modifiers are added and attack is then resolved.

In this situation, because they are not actually happening simultaneously, it also doesn't depend whose turn it is. The potential problem arises, like you mentioned, when the initial roll should have been made with advantage, as the advantage and disadvantage should cancel out. Of course, in this case, the monk wouldn't need to use Drunkard's Luck anyways.

In either situation, it seems logical to me that Drunkard's Luck could reasonably be used.

Answer 3

As they each activate at the same time, one can not be used because another was used

Since they each must activate as the attack roll is being made, which is a specific time that they can be activated, they all have the exact same time that they must be activated. One can not be activated and then the other, they would have to be activated simultaneously without taking the others' effect(s) into consideration as it does not specify that there is any range or alternate time that the ability can be activated during.

The Bard feature does throw a bit of a wrench into this argument, but the point still remains as the bard feature specifically specifies an alternate time to make the decision. Since it specifies that you can make the decision after the rolls are made, you can use it after the rolls are made. As neither of the other abilities specify this, we must revert to the base version, where it must be assumed that there is no range or alternatives to the time when the decision is made, as it does not specify any.