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This question has been answered by a Jeremy Crawford tweet here, but it is my understanding that those rulings are not valid here, so I'm hoping to find an answer in the game rules themselves.

To use the scenario conveyed in the tweet, assume a druid wild shapes into a giant octopus (which has a reach of 15 feet). The giant octopus hits a creature 15 feet away and grapples it. Can the grappled creature attack the giant octopus (which is outside the grappled creature's reach) by using melee attacks on the grappling tentacle, as Crawford claims?

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    \$\begingroup\$ After answering your question, I had a feeling that this had probably been asked before, so I searched around and a good dupe target, so I've closed this as a duplicate. \$\endgroup\$ Commented Jul 7, 2022 at 19:23

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Rules as written, no, but I allow the attack at disadvantage.

There is no rule that changes how your reach works when you are grappled. The usual rules apply whether you are grappled or not. Thus, if the target creature occupies a space that is out of your reach, you cannot attack them. It is unfortunate that Jeremy Crawford's sensible ruling is not reflected in the rules Jeremy Crawford wrote.

Naturally, this rules-as-written ruling may not be a satisfying ruling. I've tried it before, and we decided it just didn't make sense narratively. The ruling I use now is to allow attacks to be made at disadvantage. The idea there is that you should be able to have a chance at hitting, but it should be harder than if you were next to the creature. When I first implemented this ruling, we felt it was a fair compromise between the rules as written and what we felt the characters should be able to do in the narrative. Note, when the target that is grappling you is within your reach, I do not impose the disadvantage.

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RAW, no.

However this is patently ridiculous on a number of levels, from game balance to simple common sense (the creature holds you in place with their hand/tentacles/whatever and you can't touch them) such that I would suspect few if any DMs would implement those rules in that fashion.

Whether they simply ignore that interaction, houserule it, or 'interpret it' (houserule without the word houserule) I'd imagine it would not work like that.

If it does work like that, consider polymorph/wildshape options that allow you to do things based on this, as it might be incredibly potent vs melee enemies.

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