Right now, if a mob has an item in it's inventory, you can attempt to pickpocket it an infinite number of times without any risk of consequence. The only time there is any consequence for pickpocketing is when the mob has no item for you to steal. This doesn't really make any sense. It should probably be changed so that the pickpocket command has a chance to make an enemy aggro regardless of whether they have an item in their inventory, and possibly even regardless of whether you succeed at stealing an item from them.
Right now, if a mob has an item in it's inventory, you can attempt to pickpocket it an infinite number of times without any risk of consequence. The only time there is any consequence for pickpocketing is when the mob has no item for you to steal. This doesn't really make any sense. It should probably be changed so that the pickpocket command has a chance to make an enemy aggro regardless of whether they have an item in their inventory, and possibly even regardless of whether you succeed at stealing an item from them.