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I am aware that usually one has to specify who is to benefit from one's Help action. However, when it comes to using it in combat, this comment by Jeremy Crawford says:

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

However, maybe one wants to help a specific ally (e.g. enable a rogue to Sneak Attack) but initiative puts them much later in the round. Still, for some other tactical reasons, it might make next to no sense for the remaining allies to avoid attacking that target in the meantime.

Of course, one could argue that, as long as you can describe reasonably how you provide help to exactly that one specific ally without influencing the rest of the fight, something like this should be allowed. But I wonder if there is any explicit mention of this in the rules.

I've been referred to this extremely similar question: Do I choose the target or the ally for the Help action?

My main point of interest is the issue that is raised in the answer by HellSaint and the comments below it. Since this discussion is about a year old, maybe the remaining unclarities could be solved by more recent publisher's comments?

Thanks a lot for your help! (Horrible pun not intended.)

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    \$\begingroup\$ This is definitely a good question (regardless of whether or not it's been asked before). I particularly wanted to call out that the answer @Davo gave is a useful suggestion to get around this problem. \$\endgroup\$ – Gandalfmeansme May 27 at 17:57
  • \$\begingroup\$ How is this a duplicate? The other question is related, but this has an independent answer. \$\endgroup\$ – András May 27 at 18:45
  • \$\begingroup\$ Welcome to RPG.SE! Take the tour if you haven't already, and check out the help center for more guidance. \$\endgroup\$ – V2Blast May 27 at 18:55
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The Player's Handbook says on page 192, under "Actions in Combat" (emphasis mine):

Help

You can lend your aid to another creature in the completion of a task. When you take the Help action, the creature you aid gains advantage on the next ability check it makes to perform the task you are helping with, provided that it makes the check before the start of your next turn.

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.

From this, it appears that you can help a specific ally (but only their first attack gets advantage, if they have multiple attacks).

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    \$\begingroup\$ Are you making this conclusion because the term "ally" is singular? I'm not sure what about the bolded sentence brings you to your conclusion. \$\endgroup\$ – Gandalfmeansme May 27 at 17:55
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    \$\begingroup\$ @Gandalfmeansme Everything in the last paragraph is singular, this is a possible reading. \$\endgroup\$ – András May 27 at 18:47
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    \$\begingroup\$ @ Gandalfmeansme I am assuming that "friendly creature" is the ally. \$\endgroup\$ – VVilliam May 27 at 20:52
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Nothing prevents one from holding a readied action to assist a certain character on that characters turn.

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    \$\begingroup\$ This does require one to still be within 5 feet of the enemy when they get to the other character's turn so it may not always be possible. \$\endgroup\$ – Sdjz May 27 at 17:40
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    \$\begingroup\$ This may in fact be a straight forward practical solution to most instances in which this problem arises that effectively brings together the explicit reading of the pertaining section in the PHB and the above tweet by Crawford. However, it would still not reject the concern raised by V2Blast. \$\endgroup\$ – Mars Plastic May 27 at 17:41
  • \$\begingroup\$ Standard requirement for assisting still apply. \$\endgroup\$ – Davo May 27 at 20:38
  • \$\begingroup\$ Is "Help" something you can ready? "Ready" is its own action, with its own description of things you can ready. It's not clear you can just Ready any other Action. (Although the reason readying an attack only gives you 1 attack is that Extra Attack only works on your turn, not that Readying an attack is separate from Readying the Attack action. That was going to be the example I used to show it was different, so maybe I'm wrong and you can just Ready any action. Of course some like Disengage are only useful on your turn.) \$\endgroup\$ – Peter Cordes May 28 at 20:38

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