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As a bonus I will then crouch and choke them out. Don't kill them just knock them out and take only food or groshen. You can eat the food before going back to town and the groshen doesn't show up as stolen. That's a quick way to level both stealth and pickpocketing.
When you are trying to pickpocket indoors you can go and choke out everybody in the room. Then you can loot everything you need. Again, especially early in the game, don't take things that will show as stolen. Food and groshen are good bets. Don't forget to wear dark quiet clothes and get a pair of Silent Shoes.
As your speech levels up choose the Magistrate I, II, and III perks. If you're stopped for a search you can get an option to bribe the guard for 20 groshen.
The risk/reward of pickpocketing is always debatable, but that applies to street pickpocketing as well as sleep pickpocketing.
Sorry if that wasn't clear. Thanks for the other advice.
maybe you stand/crouch too close and touch the AI by mistake? because bumping into them from behind also makes them aware of you, for example when walking in the streets.
it seems a little bit random when they sleep. maybe they have a light sleep sometimes, lol
try some hours later or the next night and see if it works out better.
I'll try and if I fail I guess I'll just roll back through later when my level is higher. It's possible it's my sneak skill or something - I know I'm not getting so close that I touch him, because he is VERY easy to wake up even when I have 0 noise and all of that. Both times I tried was after waking him up a few times just trying to get close enough to get the prompt to pickpocket in the first place, forcing me to haul ass out of the house before he recognizes and pops a bounty on me. When I did finally inch in until I was close enough to pickpocket without him waking up, I pressed and held E to pickpocket (I've done awake targets multiple times, such as the Blacksmith, so I know how to do it) and it would just immediately fail, without even letting me get the medallion timer. Like as soon as I held E "You were caught" and he's getting out of bed already yelling at me. Not only that, but he would immediately have the bounty on me even if I ran before he fully woke up (something that doesn't happen when he just wakes up while I'm sneaking and I make it out before he is fully awake and walking up to me - in other words, he normally has to "catch" me).
Bottom line, mechanically something seems off with sleeping guys. Targets that are awake are way easier to pickpocket, which not only doesn't make sense, but also the game itself says sleeping targets should be practiced on iirc (I think the Miller says this) which implies they should be easier. They're not, and I can't figure out why. I imagine I will at some point.
whats your pickpocketing skill now? could be it is too low for this sleeping target.
as you dont seem to stand too close, maybe you stand too far away when grabbing in his pants?
ive read people suggest to aim for the waist because thats where the items are in the pocket.
use the padfoot potion, it should help.
or find a way to poison this guards food with a sleeping potion. youd need to spy out his dayly routines and see where/when he eats from a pot.
i dont know if NPCs eat food they find and pick up, because this way you could poison a salami or something and put it on the floor of his room before he comes home.
damn, im eager to install and replay this game again...still so many things to figure out.
but you can overweight bandits for example, when u drop in their routine way itwms with lot of weight because they grab it :)
Pickpocket skill is 4 iirc, two perks (rob people with my charisma easier, and cursor moves faster in pocket). Sneak is 3. Just got those levels robbing guards and smiths though, it's not hard even at minimum level as long as they or nobody else sees you and you have 0 noise. Just, can't rob sleeping Pazdera lol (haven't tried any other sleeping targets either, doing other things).
Pickpocketing is a skill check using circumstances and skill levels.
Related items are Noise, Agility, Stealth Skill, Pickpocket Skill, and Circumstance (like sleeping or awake), and maybe others.
How the check works (just a review):
You can fail a Pickpocket Check immediately, meaning right when you start holding the "E". You can also fail shortly after, before the clock winds past the important marker. The other fails are rather obvious.
Chance of success ?:
Pickpocketing from sleeping targets, as a circumstance, is much much harder than pickpocketing from awake targets. It is simply stupid hard.
I have never successfully pickpocketed from a sleeping target with under a 5 in Pickpocket and 8 in Stealth. It's simply too hard.
As far as a CONE, i have noticed that being just below the waist to be the best location, but i think this has to do with distance, since distance does affect likelihood of success.
So, if we consider the waist to be the center of the target, then you need to be the proper distance from the waist to maximize you chances of success. Not too close, not too far.
Hope it helps
i was sneaking crouched infront of his face and another time infront of his belly region. i got a green window for around 15 seconds while picking his pockets.
so i dont think there is a vision cone when NPCs sleep.
i used my fully upgraded 180Hrs Henry build with good sneaking/no-visbility/no-sound clothes though...
it sure can happen that NPCs wake up though, had that happen too. maybe rng is involved.