Have had this issue too when i level'ed in SK.
Just like Uthgaard said, it happens with same pet. one moment it procs, 10 sec. later you get the insufficient will message.
For me it seems like the system is coded to do some kind of lvl or dmg check every time the pet gets a proc from it's weapons, and sometimes it gets a value that makes the system believe the pet is too low lvl for the wep. to proc.
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