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D&D 5E Multiple Grapples

D&D 5E.

Suppose a creature with multiple tentacles can grapple with each tentacle, either one creature or multiple creatures. It chooses to grapple a single creature with multiple tentacles. Does the creature need to Escape each grapple individually? Or does one Escape roll end multiple tentacle grapples?

What say you?

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Rotten DM
If Correctly Remember I, a critter can only grapple a creature once. But success escape roll beats multiple. So I say!


Title? I don't need no stinkin' title.
By strict reading of the rules, my ruling would be that an escape attempt must be made against each grapple.

But that means that a PC grabbed by all 6 tentacles of a roper is just SOL since they will never have 6 escape attempts. Unless someone else can make the escape attempt for the PC of course.

So I'd probably just make it disadvantage to escape the grapple if grappled more than once so the PC has a fighting chance. Maybe give the attacking monster advantage if the PC is grabbed by more than two tentacles [edit: or if the PC already has disadvantage because they're restrained.]


The action of "escaping a grapple" ends all grappled conditions on someone. They make one strength(athletics) or dexterity(acrobatics) check, and if it succeeds they are no longer grappled.

Everyone who has the target grappled can contest it. Each makes a strength(athletics) check. Each person grappling that they beat (or who chooses not to contest) is no longer grappling them. If they beat everyone, they are free.

This is, as far as I can tell, a reasonable RAW reading. No rules state that "Escape a Grapple" has to be done for each grappler, it simply states they can "escape a grapple" and what check and what contests it. So I chose not to add that (also reasonable, but unwritten) requirement in.


If you have something grappled 10 times, you don't get to contest it 10 times. This follows from the above.

If you are a roper using 6 tentacles, arguing it has advantage on its check is reasonable; that is what advantage is for.

OTOH, if 3 huge creatures all try to grapple the same small creature, I might argue that they interfere with each other and grant each other disadvantage (there simply isn't enough room!)


Title? I don't need no stinkin' title.
LOL. The help of "there are two completely different ways of ruling that you probably already knew?"

I don't follow the letter of the rules because that's just not how the books are written. We've just always treated multiple grapples (in the very rare cases it's come up) as separate things.

But the issue I have with 1 check to escape them all is that a Roper for example has a fixed DC of 15 to escape. Escaping 1 grapple is no more difficult than escaping 6. So maybe 1 action but 6 checks would be another option. Do what makes sense for you and your group.

Ha! Yeah, but you all give me stuff to think about. The Roper example is exactly what I'm dealing with now. I'm leaning toward it being 1 action, but roll for each grapple. I can imagine someone heroically escaping a bunch of tentacles... but also a hero escaping all the tentacles, except that one still holds their ankle...