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Message: <blockquote data-quote="DrunkonDuty" data-source="post: 4963250" data-attributes="member: 54364">Wow. Tricky. Let me preface my answer by saying I don't like the DnD grapple rules and think they need to re-written and clarified/simplified. The following is just the way I'd run it. 1) & 2)  Yes. All in one great big pile. A 5 foot square is quite large really, especially if everyone is piled on top of one another. As GM you have to decide when there's too many  people to fit in one square. And also when there's too many people trying to get a hold on one individual and you say, "No-one else can get close enough to the target." 3) You could run it several ways I think. Either a whole bunch of individual grapple checks. Each result determined separately. Each result applied separately. OR one grapple check, each side having a Main Grappler and everyone else merely using the Aid Another rules. OR one BIG grapple check: Everyone adds all their grapple bonuses together and each side makes one check. I'd use the different methods depending on the situation. Of course then there's iterative attacks. Oi. Also don't forget that the Monk can use their unarmed attacks against someone who has them grappled (but not pinned.) Also they count as armed so if someone attempts to grapple them without the Improved Grapple ability the Monk gets an AO on them. Good luck.</blockquote>