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When I use the Help action, do I choose the monster to distract (and then the next ally to attack gets advantage) or do I choose the ally and the monster (so that only his attack against that target gets advantage)? Or something else?

Help

[...]

Alternatively, you can aid a friendly creature in attacking a creature within 5 feet of you. You feint, distract the target, or in some other way team up to make your ally’s attack more effective. If your ally attacks the target before your next turn, the first attack roll is made with advantage.

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For ability checks, target ally. In combat, distract enemy instead of targeting ally.

According to the 5e Dungeon Master's Screen Reincarnated, it's both.

You help one creature with a task, giving that creature advantage on the next ability check it makes for that task. Or you distract one creature within 5 feet of you, and the next attack roll that an ally of yours makes against that creature has advantage.

Whichever option you choose, the advantage goes away once used or when your next turn starts.

So basically out of combat you help your ally (target: ally), in combat distract enemy (target: enemy)

After the help is used by one player, the nobody else gets advantage from it (from the updated DM's Screen).

Rules as written, you don't get to choose a player to help during combat, but my DM homebrews that you can choose to help a specific player instead of distracting a specific enemy.

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    \$\begingroup\$ Also, welcome to RPG.se. Please take our tour. Note that we're interested in detailed answers from experience or textual evidence, so your answer could be improved by giving that. \$\endgroup\$ – HellSaint Jul 29 '18 at 4:07
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    \$\begingroup\$ @HellSaint Thanks for the critique, added my source. \$\endgroup\$ – John Carroll Jul 29 '18 at 4:28
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    \$\begingroup\$ Note that 5e has a good amount of info under OGL (in the SRD), including the combat section where the Help action is described. Interesting enough, the wording on the screen contradicts the wording in the books. \$\endgroup\$ – HellSaint Jul 29 '18 at 5:25
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    \$\begingroup\$ This answer is correct. Jeremy Crawford confirms it here: "If you use the attack-aiding option in Help, the next ally who attacks the target gets the benefit." \$\endgroup\$ – V2Blast Jul 29 '18 at 8:03
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Current RAW (or at least my reading on it)

Alternatively, you can aid a friendly creature in attacking a creature within 5 feet of you. You feint, distract the target, or in some other way team up to make your ally’s attack more effective. If your ally attacks the target before your next turn, the first attack roll is made with advantage.

This wording specifies a singular ally. It doesn't say "the next ally that attacks"1 or "your allies' attack" or "If one of your allies" or anything similar, which strongly implies it affects only one ally, which is chosen by you.

Additionally, note that distracting the enemy is one possible way to help, but there are others. In particular, note this sentence. Again, this implies that interacting with the enemy creature itself is not even needed.

or in some other way team up

Conclusion: You help your ally (one specific ally) in attacking a creature.


Rules as Intended is different, though

1 According to John Caroll's answer, it actually does say that in the 2017 DM Screen. I would expect some clarification or errata on the PHB from that. The "in some other way team up" is also excluded and distracting is the only way to help in combat.

Or you distract one creature within 5 feet of you, and the next attack roll that an ally of yours makes against that creature has advantage.

This wording is consistent with the answer by Crawford in twitter

If you use the attack-aiding option in Help, the next ally who attacks the target gets the benefit. #DnD

Note that this answer is inconsistent with this other answer from him.

Q: Can a Mastermind Rogue use the Help action as both a normal Action & a Bonus Action in the same turn to assist 2 different PCs in combat?

A: Yes.

Since the advantages would simply "stack up" in the same attack and be lost2. Note that the tweet about assisting two different PCs is more recent than the tweet directly saying "the next ally attacking gets the advantage".

If the intended is that the next person attacking gets the advantage, an errata should be published for that, IMO.

2 As noted by V2Blast, this is not true if two different enemies are chosen - but the wording in the question is, at least, unclear.

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    \$\begingroup\$ This answer is incorrect, according to Jeremy Crawford: "If you use the attack-aiding option in Help, the next ally who attacks the target gets the benefit." \$\endgroup\$ – V2Blast Jul 29 '18 at 8:04
  • \$\begingroup\$ @V2Blast Took into account now. Also added another tweet which contradicts this. \$\endgroup\$ – HellSaint Jul 29 '18 at 21:51
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    \$\begingroup\$ I've seen that Mastermind tweet... I'd say it doesn't necessarily contradict the tweet I linked, since you could Help against two different targets, but the curtness of the answer and the lack of context/elaboration by the person he was responding to does definitely make it unclear. \$\endgroup\$ – V2Blast Jul 29 '18 at 21:53

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