Just wondering about this. I'm new to this pickpocketing business (I forget what level I'm at) but I have the perk to place poisons on the target and have them consume them. I was doing a DB quest to kill a guy checking on security measures for the Emperor. I followed him into Castle Dour where he took a seat at a table in the barracks. I gave him a paralyzing potion (7 seconds, IIRC) and he slumped in his chair. However, even though it said "pickpocket so-and-so" pressing the "A" button did nothing. It wasn't until the potion wore off that I could pickpocket him again. I might as well have taken the potion myself. Is this how it's supposed to work? If so, what's the point?