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The PHB p195 (Escaping a Grapple) describes how to break free from the condition but, once free, I assume the grappled creature stays where they are, on a threatened square and therefore attack of opportunity rules apply.

However if the grappler was humanoid and it grappled you with their arms/limbs, I can't imagine how they could attack you when you are escaping because in order to grapple you they would have to sheathe or drop their weapons and, therefore, can't attack you with anything other than their limbs (bludgeoning 1 damage) when you try to leave.

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A grapple only takes one hand

So, after they grapple you, and trip you so you can’t stand up because the grapple reduces your speed to 0, they can then wail on you with that long sword they are holding in their other hand, with advantage because you are prone. Why do you think they started the grapple in the first place?

If you break the grapple, your speed is restored and you can then move. They still have that long sword of course, so if you move without Disengaging they’re going to use it to cut you with an opportunity attack. If you are smart, you stood up first so they don’t have advantage but you can only move with the half of your movement you have left, so about 15 feet. You know they’re coming to grapple you again on their next turn, right?

Of course, breaking the grapple is problematic: they almost certainly started it because their Strength (Athletics) is better than yours, or your Dexterity (Acrobatics). Smart enemies don’t grapple fighters or rogues: they grapple wizards or warlocks or other wusses.

I was DM for a party in Tyranny of Dragons who worked out that the best way to kill a dragon was for the Bard to polymorph the Barbarian into a Great Ape who has a much better grapple ability than any dragon, grapple the dragon whereupon the Sorcerer would drop a Wall of Fire on it (cold side to the ape) plus other non-concentration stuff, the Cleric would use Cloud of Daggers plus other non-concentration stuff, the Bard would stay out of the way and the Barbarian would rage and hit the dragon - 2 rounds maximum.

Notwithstanding

An unarmed strike has a reach of 5 feet anyway ... pray it is not a monk grappling you.

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    \$\begingroup\$ I thought polymorphed creatures lost their sense of reasoning, they literally became the beasts, and might just rampage around or run away. Is this a homebrew rule of your table or have I been misinterpreting the spell? \$\endgroup\$ – BlueMoon93 Dec 19 '17 at 9:54
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    \$\begingroup\$ @BlueMoon93 A creature polymorphed into another creature "retains its alignment and personality", which I interpret to mean that it keeps as much of itself as the new form has space for in its mental scores. So a person who turns into an ape would be as close to their original selves as an apelike brain allows. In most cases - even relatively unintelligent beasts - this would allow them to remember who their friends are and comprehend the rough idea that they're fighting the big scaly thing. Even feeblemind says the victim can still "identify its friends, follow them, and even protect them". \$\endgroup\$ – anaximander Dec 19 '17 at 10:19
  • \$\begingroup\$ @anaximander TIL \$\endgroup\$ – BlueMoon93 Dec 19 '17 at 15:29
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Yes. An opportunity attack can be made without weapons (or hands, or anything...).

You can make opportunity attacks even with unarmed strikes. And remember, unarmed strikes don't have to be punches, they can be a headbutt or a kick.

So, your grappler might have dropped one of his weapons (since you only need 1 hand to grapple, like Dale M said), or even dropped his two-hander, or even have the other hand occupied with something, and he can still attack you.

Barbarians, Brawlers, and Monks are particularly great with opportunity attacks, as they add a lot of modifiers on top of the unarmed strike.

Finally, it also triggers attacks from any other enemies around it, so consider the Disengage action when trying to break yourself from grapples, or forced movement (such as Shove, and Thunderwave), or Teleports, etc. Ways to move without triggering OAs can be found here.

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  • \$\begingroup\$ "consider the Disengage action when trying to break yourself from grapples" but breaking a grapple takes 1 action, so you can't escape with Disengage on the same round that you break from a grapple, right? \$\endgroup\$ – Juan Alonso Jan 6 '18 at 6:49
  • \$\begingroup\$ For most classes, you couldn't "break from grapple" and "disengage" in the same turn, no. But Rogues can Disengage as a bonus action, Fighters can Action Surge, anyone can be buffed with the Haste spell, and I'm sure there are more ways of doing it :P Finally, if someone breaks the grapple for you, or if you break it on another turn, you still might want to get away, and Disengage is a decent option then \$\endgroup\$ – BlueMoon93 Jan 6 '18 at 11:47

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