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A PC in my campaign has an enemy grabbed and prone and is attempting to drown them. It's the enemy's turn. Can the enemy escape while grabbed?

If so can he shift while prone if he succeeds on an escape?

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Couple of things:

  1. It's perfectly acceptable to stand up while prone and grabbed (grabbing immobilizes, but immobilization does not prevent standing from prone).

  2. Yes, he can absolutely use acrobatics/athletics to escape, but he'll be prone and as such will not be able to use the free shift.

This makes grabbing and proning an effective strategy as it means the monster needs to consume 2 move actions to be able to move freely.
A smart one will not do so however, as creatures without any melee or close attacks are very rare. Being grabbed gives no penalty to attacks or defenses. So the best tactic for them is to Stand up and attack in the first round, then Escape and attack in the next.

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As usual with 4E, it is worth stating that the condition prone and the act of "standing up" do not have to be taken literally in descriptions. The enemy doesn't have to be visualised as flat on it's back at the start of standing up, nor does it have to be imagined as somehow ignoring being held and freely standing up. It just goes from unable to walk or shift and granting combat advantage, to being more capable of movement. One suggestion - it manages to roll or move around in the grab and get a leg down onto the floor for leverage. –  Neil Slater Oct 29 '13 at 19:18

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