
Quandary |

By the RAW, I think you could,
but again, by the RAW only the "Damage Option" for 2nd-successful Grapples does damage in the first place. I think appling critical Unarmed damage (or whatever you're using to do the Grapple) on INITIAL Critical Grapples is completely reasonable (assuming it succeeds, I don't believe Maneuvers automatically succeed on 20s) but that would more or less be in the realm of house-rules, for the above reason.

hogarth |

(assuming it succeeds, I don't believe Maneuvers automatically succeed on 20s)
They do:
"Determine Success: If your attack roll equals or exceeds the CMD of the target, your maneuver is a success and has the listed effect. Some maneuvers, such as bull rush, have varying levels of success depending on how much your attack roll exceeds the target's CMD. Rolling a natural 20 while attempting a combat maneuver is always a success (except when attempting to escape from bonds), while rolling a natural 1 is always a failure."

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Is it possible to do a critical hit with a grapple for double damage?
On the one hand, it says that combat maneuvers are attack rolls, but on the other hand, it doesn't mention critical hits (only that a natural 20 is an automatic success).
I would say yes IF you're attack with a hand held light weapon, anatural attack or have improved unarmed strike.
http://paizo.com/pathfinderRPG/prd/combat.html
"Grapple
As a standard action, you can attempt to grapple a foe, hindering his combat options...
Damage: You can inflict damage to your target equal to your unarmed strike, a natural attack, or an attack made with armor spikes or a light or one-handed weapon. This damage can be either lethal or nonlethal."
Mike