- you can only pickpocket each NPC once (I think this is to prevent people from exploiting shopkeepers);
- you can only pickpocket in sneak mode;
- the character must have at least one point in pickpocket;
- each time you take an item, the value and weight bar at the top of the victim's inventory will start to fill. Objects will darken (and cannot be stolen) if the value or weight of these objects exceed the available limit on the bar. The higher the character's level in pickpocket, the more you can steal.