
DMBrendon |
On CRB pg. 200:
"Humanoid creatures without two free hands attempting to grapple a foe take a -4 penalty on the combat maneuver roll."
"If you are grappled you can attempt to break the grapple as a standard action by making a combat maneuver check"
Does this mean that if a PC with 2 free hands is grappling an opponent with a shield or holding a weapon, the opponent gets -4 when trying to escape the grapple? Or does that penalty only count when starting the grapple?

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You only take the penalty when initiating the grapple with one hand.
As a standard action, you can attempt to grapple a foe, hindering his combat options. If you do not have Improved Grapple, grab, or a similar ability, attempting to grapple a foe provokes an attack of opportunity from the target of your maneuver. Humanoid creatures without two free hands attempting to grapple a foe take a –4 penalty on the combat maneuver roll. If successful, both you and the target gain the grappled condition. If you successfully grapple a creature that is not adjacent to you, move that creature to an adjacent open space (if no space is available, your grapple fails)....
If you are being grappled...
If you are grappled, you can attempt to break the grapple as a standard action by making a combat maneuver check (DC equal to your opponent's CMD; this does not provoke an attack of opportunity) or Escape Artist check (with a DC equal to your opponent's CMD). If you succeed, you break the grapple and can act normally. Alternatively, if you succeed, you can become the grappler, grappling the other creature (meaning that the other creature cannot freely release the grapple without making a combat maneuver check, while you can). Instead of attempting to break or reverse the grapple, you can take any action that doesn’t require two hands to perform, such as cast a spell or make an attack or full attack with a light or one-handed weapon against any creature within your reach, including the creature that is grappling you. See the grappled condition for additional details. If you are pinned, your actions are very limited. See the pinned condition in Conditions for additional details.
There is no mention of a penalty of only having one arm free.

Iron Giant |

I've put a lot of thought into the grapple rules, so here is my take on it:
The initial grapple and all grapple checks done by the controlling grappler are "grapple checks". The check done to escape or reverse a grapple is actually a different type of check despite the secondary grappler possibly gaining control of the grapple with a check. If you look at various feats/traits/abilities, you'll notice that the two appear to be discrete. That being said, I think the two available hands penalty only applies to "grapple checks" so it wouldn't apply to escape attempts.