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Let's say my party is attacking a dragon. I'm a Mastermind rogue who can use Master of Tactics to use the Help action as a bonus action if I'm within 30' of the dragon. Can I specify who in my party I'm giving the help to? Or will it necessarily be the next player who attacks the dragon?

Let's say the paladin in my party has his turn next and he decides to attack the dragon... but I'd really like to give advantage to the other rogue in my party who goes after the paladin. Can I specify that I'm helping the rogue?

If so, how would this be role-played to make some kind of logical sense? How would it play out?

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You must specify the creature you're helping, so your scenario works

The Help action in the PHB states (192),

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.

This section implies that you are giving your aid to another creature. In other words, the creature you're helping is the target of your help action. Therefore, you can choose to use your help action on the rogue. In this particular scenario, you must choose who you're helping: you can help the rogue, or the paladin, but to help with a condition like "whoever attacks the dragon next" you need to ready an action, which you can't do as a bonus action.

Given that you're a "master of tactics," such aid would be as simple as calling out a perceived, momentary weakness, or giving a word of strategic advice. Something like "The dragon has exposed his underbelly on the left!". The advantage only lasts for a single attack, and only for a single turn, so it has to be something brief.

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  • \$\begingroup\$ Thanks for your reply Icyfire. This was my original interpretation of Help as well, I'm not sure why you've been downvoted. I asked the question because in my research I had found videos that said my interpretation was wrong... but nowhere could anyone point me to the rules to clarify further. I think your interpretation of how this would play out in roleplaying makes a lot of sense. \$\endgroup\$ – Queebo Sep 8 '18 at 13:14
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    \$\begingroup\$ @Queebo Glad to have helped! I think I got downvoted because I leapt to answer instead of calling out the duplicate, which is a fair reason to get downvoted, I think :/ \$\endgroup\$ – Icyfire Sep 8 '18 at 22:22
  • \$\begingroup\$ @Icyfire: The other reason for downvotes may be that the answer may be wrong, at least based on designer intent - as suggested by the top answer to the question this is marked as a duplicate of (and the "rules as intended" portion of the other one). \$\endgroup\$ – V2Blast Feb 17 at 9:30

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