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The rules for grappling require:

The target of your grapple must be no more than one size larger than you, and it must be within your reach. (PHB, p. 195, italics added)

Normally, this would mean that you must be within 5' of a creature to grapple it. But some creatures have a longer reach. For example, an Ancient Red Dragon could grapple a creature with its claws which is 10' away from it (an odd use of its action, but whatever).

Jeremy Crawford has already indicated that if you're grappled, you can still attack the creature grappling you even if their space is outside your reach, since you can attack the arm/tentacle/appendage that is holding onto your body. But I wondered about a similar situation: ranged attacks.

The rule on making ranged attacks while an enemy is nearby states:

When you make a ranged attack with a weapon, a spell, or some other means, you have disadvantage on the attack roll if you are within 5 feet of a hostile creature who can see you and who isn’t incapacitated. (PHB, p. 195, italics added)

So if you are grappled by a creature who is 10' or more away from you (but you're in its reach), and you make a ranged attack, do you have disadvantage?

On the one hand, you are more that 5' away from its space. On the other hand, part of its body is definitely within 5' of you, since you're grappled by it.

Is there any definitive answer to this question? I've tried to search similar questions and sage advice, but without success.

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RAW, grappling with reach doesn't impose disadvantage

There are no rules stating that being within a monster's reach imposes disadvantage. The rules explicitly say "within 5 feet", not "within an enemy's reach". Grappling, unless otherwise stated, does not naturally impose disadvantage to attacks by itself.

Grappling does say this:

When you want to grab a creature or wrestle with it, you can use the Attack action to make a special melee attack, a grapple. If you’re able to make multiple attacks with the Attack action, this attack replaces one of them. [...] The [grappled] condition also ends if an effect removes the grappled creature from the reach of the grappler or grappling effect [...]

So if you are not within 5 feet, and grappling does not impose disadvantage, and grappling relies on reach rather than adjacency, then being grappled at that extended reach will have no effect to your ranged attacks.

This does bring up a possible question as to how movement/positioning works after being grappled with reach, but that may be grounds for a different question.

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    \$\begingroup\$ Because of the double negatives involved in my question, you might want your answer's title line to be a bit more direct. Like "The Attack would not have disadvantage, according to RAW." \$\endgroup\$ – Gandalfmeansme Aug 13 '18 at 22:34
  • \$\begingroup\$ @Gandalfmeansme Good point! Fixed it! \$\endgroup\$ – Daniel Zastoupil Aug 13 '18 at 22:35

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