I have level 17 Pickpocketing, level 20 stealth, my clothes make zero noise, and my visability 24 and conspicuious at 25. And I still instant fail at pickpocketing a sleeping person! I’m damn neaer a master, I should be almost able to pickpocket a king at this level. And I’m still being instantly caught by some nameless peasent who is asleep!
This skill is so damn annoying. It’s a good think that I made 500+ save potions just so I wouldn’t completely destroy my characters reputation and mad the game almost impossible to play in some towns.