Improved Steal for reference.
Benefit: You do not provoke an attack of opportunity when performing a steal combat maneuver. In addition, you receive a +2 bonus on checks made to steal an item from a foe. You also receive a +2 bonus to your Combat Maneuver Defense when an opponent tries to steal an item from you.
It doesn't seem to specify that the +2 is limited to only whilst performing a Steal Combat Maneuver during a fight. As far as I can tell, it should apply to Sleight of Hand checks to pickpocket out of combat too. Am I right?
I'd give it to you, but I'm not entirely sure that's the intent, as all the Improved Maneuver feats are worded like that.
In addition, you receive a +2 bonus on checks made to grapple a foe.
In addition, you receive a +2 bonus on checks made to trip a foe.
In addition, you receive a +2 bonus on checks made to sunder an item.
And so on...
I would say yes, considering it says you get + bonus to steal an item from a foe and doesn't say "in combat". It also doesn't say +2 with the Steal combat maneuver. It simply says, "steal an item from a foe".
Thanks guys. I'm making a Pilferer Familiar, which gets Improved Steal as a bonus feat. The feat seems strangely useless since most familiars are tiny and get a -2 to CMB to use the Steal maneuver in the first place. Makes much more sense for it to add to the Sleight of Hand skill (which Pilferers get as a class skill).
So, being tiny, your familiar would only be snatching things from peasants.