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In my current OOTA Group my party fought against a rocktopus. They attacked them from the ceiling out of reach for melee attacks.

Is it possible for the players to ready an attack with the trigger "when one of the tentacles attack I'm gonna hit it"?

Normally I would say no. If your target attacks you with a weapon with more reach and is out of your reach it shouldn't be possible to hit them with your readied action. But the melee weapon (the tentacle) is part of the rocktopus and I am not sure how to handle this situation.

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You sure can.

Even if you couldn't by the rules as written, I would suggest allowing it to reward player ingenuity, and allow for diversity in combat. However, this overruling is not necessary because the rules permit this action:

Choose a target [for the attack]. Pick a target within your attack’s range: a creature, an object, or a location.

While the tentacle is attacking you, the creature is within range and is therefore a valid target. This is further supported by the lead game designer, Jeremy Crawford, on Twitter when he answered a similar question (while not an official ruling, it lends credence to my ruling above):

A creature grappled by a giant octopus can attack the octopus via the grappling tentacle.

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    \$\begingroup\$ This... is uncomfortable. Being in a grapple does not have the same timing context as being the target of an attack. I don't think this quote applies to the original question. \$\endgroup\$ – João Mendes Apr 29 at 16:19
  • \$\begingroup\$ @JoãoMendes That's why I mentioned it only as cursory evidence (which it would be anyway as it only speaks to the rules intent as clarified by one of the designers). My official ruling refers to the fact that the creature is within range \$\endgroup\$ – David Coffron Apr 29 at 16:21
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    \$\begingroup\$ How does this ruling interact with other rules like attack of opportunity? Do PCs get to swing back each time they are attacked by a tentacle with reach? \$\endgroup\$ – Winterborne Apr 29 at 17:14
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    \$\begingroup\$ @Winterborne no, because the rocktopus is not "moving" out of reach. \$\endgroup\$ – David Coffron Apr 29 at 17:18
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    \$\begingroup\$ @Winterborne because the tentacles are not the creature. They are a part of a creature so they can be targeted as a creature, but attacks of opportunity require "movement" (the game term), as in expending part of your speed (or movement gained from something else) \$\endgroup\$ – David Coffron Apr 29 at 17:40

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