Hello,
There have been a couple of threads regarding pickpocketing and asking how it works with the "Loaded Pockets" Berath's Blessing. If you want information on Loaded Pockets, you can go here.
In anticipation of the new patch, I decided to do a deep dive and try to figure it out. To pickpocket an item, you need to be actively in stealth. When you activate a pick pocketable creature, you will see it's pick pocketable inventory. Items that cannot be pick pocketed are greyed out but show