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I have three attacks this round. Let's assume I have access to many tiny free thinking minions who obey my command, but don't require an action to do so on my part.

Can each minion use the ready action in turn, to help distract the opponent I am fighting between each of my attacks, granting me advantage on all my attacks?

If I somehow had ten attacks and ten tiny minions would it still work?

What is the limit of attacks/creatures able to use the help action in combat with me?

Official WotC rules only please, no UA.

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With suitable timing, each help action grants advantage on one attack

As you've surmised, for this scheme to work all the helping creatures except the first one must ready actions with triggers of "after my ally's first attack", "after my ally's 2nd attack" and so on, because if they all took the help action before your turn, then all the extra help would stack up on your first attack and be wasted, since multiple sources of advantage don't stack. However, assuming you can organize all your helpers appropriately, there's no reason that each help action can't grant advantage on one attack, giving you advantage on as many attacks each round as you have helpers. Obviously at some point you could run into other limits such as the number of helpers able to get into melee range, but the vast majority of the time, the limiting factor will be the number of attacks you can make in one round.

Each help action grants advantage on the next attack

I'm claiming that each help action grants advantage on the next attack, but the wording of the help action doesn't fully spell this out, so let's think about it a bit. The relevant part is:

If your ally attacks the target before your next turn, the first Attack roll is made with advantage.

Which attack roll is the "first" one? It's a bit ambiguous. Clearly it's not the first attack roll of the campaign, and it probably doesn't mean the first attack made by the ally during the current combat. That would make the help action mostly useless after the first round. Hence, the "first attack roll" must be implicitly referring to the first attack roll within a certain time period. The end of that period is given explicitly: it's the start of the next turn of the creature taking the help action. But when does it start? The only start point that makes any sense is when the help action is taken. Hence, if multiple help actions are taken at different times using readied actions, they can grant advantage to different attacks made by the same creature during a single turn.

In other words, the wording above is equivalent to (addition in bold):

If your ally attacks the target before your next turn, the first Attack roll after you take the help action is made with advantage.

Presumably, the text doesn't specify this explicitly because usually it doesn't matter. The only time it would be ambiguous is if a creature readies a help action to be taken during another creature's turn, which is a rare occurrence. And it is well established that 5e doesn't try to spell out rare interactions in the rules, but instead expects the DM to handle them.

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    \$\begingroup\$ Tiny servant stipulates that when you have multiple servants, all servants must be given the same command. How are you getting the servants to organize appropriately with the same command? \$\endgroup\$ – Thomas Markov Jul 21 at 12:56
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    \$\begingroup\$ @ThomasMarkov The OP has clarified that they are asking about the mechanics of the help action, not the mechanics of the Tiny Servant spell. (Ideally they should reword their question to remove any reference to the spell.) \$\endgroup\$ – Ryan C. Thompson Jul 21 at 12:58
  • \$\begingroup\$ Ah, I see that now, I will see if I can get the question reworded appropriately. Thanks for pointing that out. \$\endgroup\$ – Thomas Markov Jul 21 at 13:00
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    \$\begingroup\$ @Lovell Correct, with proper coordination the only limits are the number of attacks available and the number of allies able to take the help action. \$\endgroup\$ – Ryan C. Thompson Jul 21 at 13:16
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    \$\begingroup\$ Ryan sorry I was being a bit flippant (non-pejoratively!), but suggesting that you might edit the question to lead with that answer, then follow with the explanation \$\endgroup\$ – Lovell Jul 21 at 13:29
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Strictly, if you wanted to follow the rules as written:

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.

Not an attack roll, or the attack roll but the first attack is made with advantage.

Is this over simplifying? Probably, but it is the rules as they appear.

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    \$\begingroup\$ You could argue that it's the first attack you make after the help action is given, and then it still applies. \$\endgroup\$ – Sam Lacrumb Jul 21 at 9:03
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    \$\begingroup\$ "If your ally attacks the target before your next turn, the first Attack roll is made with advantage" - that seems pretty clear to me, regardless of how many attacks you have, you have one, and only one, first attack. And then the wording would surely by "the next attack" otherwise? \$\endgroup\$ – Steve Jul 21 at 9:07
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    \$\begingroup\$ surely "first attack roll" here means "first attack roll subsequent to your taking the help action"? \$\endgroup\$ – Lovell Jul 21 at 9:14
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    \$\begingroup\$ No offense but is that what it says? That's an interpretation you're free to apply but RAW it simply doesn't say that. \$\endgroup\$ – Steve Jul 21 at 9:46
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    \$\begingroup\$ If you think "first attack roll" doesn't mean "first attack roll after the help action is taken", can you define "first" in this context? First attack roll made by that character during the current round? First attack roll of this combat? First attack roll of the campaign? To me, there's no other timing that makes more sense than "first after taking the help action". \$\endgroup\$ – Ryan C. Thompson Jul 21 at 12:24

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