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Suppose the following situation: I want a familiar to give me advantage on melee attacks via the help action. However, I do not want to be yet another adventurer with an owl familiar doing fly-by helps. Instead, I pick something smaller (say, a spider), and have it ride on me.

My idea is thus: The familiar, on its turn, readies an action to help me whenever I attack anybody. Seeing as I close to melee to do that, the familiar is within both 5ft of whoever they're helping and the target, satisfying the range requirement. Is there a RAW reason this shouldn't work?

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    \$\begingroup\$ @PurpleMonkey: I don't think this is quite a duplicate, in the sense that it asks about readying a Help action - but it would be improved by being edited to focus specifically on whether it's possible to Ready a Help action. (Answers could then address whether there's any benefit to Readying it - I can think of one, in OP's case or in any similar one.) \$\endgroup\$ – V2Blast Apr 29 '20 at 0:40
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    \$\begingroup\$ @V2Blast I agree the OP might be trying to ask something different from the dupe but as written it’s a clear dupe. If the OP clarified their thoughts in a new question .., \$\endgroup\$ – Dale M Apr 29 '20 at 1:00
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    \$\begingroup\$ Not a duplicate — this questions asks about familiar riding its master and readying the Help action. The linked question asks "can a familiar take the Help action" in general. \$\endgroup\$ – enkryptor Apr 29 '20 at 10:11
  • \$\begingroup\$ @PurpleMonkey Yes, this is a different question ; it's about readying the familiar's help action, not using the help action on its initiative order; (In the case of an owl, that may include the fly by feature, so this could be a somewhat complex answer). As I look into the details, I see a number of moving parts. \$\endgroup\$ – KorvinStarmast Apr 29 '20 at 12:49
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This is legal

Help is an Action you can take. Ready lets you prepare an Action you can take to be used with your Reaction when a specific trigger is met.

Exerpt from PHB pg. 175, Working Together:

A character can only provide help if the task is one that he or she could attempt alone.

Here's the portion on Help, PHB pg. 192:

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.

A familiar can't take the Attack action, but nothing is preventing them from using the Help action.

PHB pg. 240:

A familiar can’t attack, but it can take other actions as normal.

Help is an Action that can be taken, just like Dash, Dodge, and Hide are.

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You can do this

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.

[PHB, Chapter 8, Actions in Combat, Help]

If the familiar uses its Action on its turn to Help you fight a foe then you have advantage on your first attack on your turn.

If the familar uses its Action on its turn to Ready to Help you and on a subsequent turn uses its Reaction to Help you then you have advantage on your first attack on your turn.

What's the difference?

In the second situation, the familiar waited to Help until it was close enough to the foe to be able to help. This did require the use of its Reaction, however.

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