Basically, if you want to level pickpocketing in this game, you have to save before getting behind someone, pickpocket and hope they don’t instantly catch you, save the game, and reload – and in the process, you screw up countless times, forcing countless reloads. It’s incredibly tedious and it feels downright unfair when you’re caught the instant you press E.
I’m going to wear my SSD out just by saving and loading my game a hundred thousand times. =/
So…you’re doing what people do in Skyrim, so there’s no “risk” then? Pickpocket is meant to be about risk. If you get caught, oh well, just claim you have no cash and go to jail.
But if you’re finding it hard, a good way to level it is to wait until you’re staying at an Inn, sleep until the early hours of morning (I think most NPCs wake around 6am?) around four or five, your game has saved, and pickpocket the sleeping people in rooms (the staff for example). They’re easier to pickpocket when sleeping as there’s no witnesses and they’re less alert. This is a good way to also do lockpicking and thieving…if you bugger up, you can go back to your sleep save I suppose and try all over again without losing your saviour schnapps.
It feels too risky, though. Let’s not confuse difficulty with tediousness. It feels like RNG punches me in the mouth whenever I mess up and I get caught, and the thing is, it seems like sleeping NPCs catch me just as often. It’s annoying, not difficult.
It’s easy to level Pickpocketing in safety.
You get to the Mill at Rattay at the beginning of Awakening main quest, and have the chance to learn Pickpocketing from Miller Peshek.
You do this with him to steal his dagger to learn the basics.
But once you succeed and complete this side quest, you can talk to him again and repeat the same quest by taking the do it again option. Just keep practising with no danger and no penalty for failure with him and raise your skill.
It has the added bonus of levelling Stealth also at the same time. All for free and no dangers.
After a few levels you will have learnt the system better and gain more time and grab the first perk ideally will help for future efforts.
There is a decent guide on how to get the side quest and tips of the skill may help.
GL
Ahhh… I didn’t realize you could level pickpocketing just by doing that training mission. I figured it was just for practice rather than actual skill leveling. That’s helpful to know. 
It’s too bad Peshek’s lockbox only re-locks a finite number of times, because I’m starting to run out of doors and chests to unlock…
Its really difficult in the beginning when you have a low skill in both pick pocketing and stealth. Be sure to follow Pesheks advice and target sleeping people, and when you do be sure that the clothing you currently have equipped aswell as your weapons aren’t making to much noise.
Its a factor that is easily over looked because people wanna play this like skyrim where stealth is only based on crouching and your level.
Even with my pick pocketing maxed out and my stealth maxed out you will find it hard to get away with pick pocketing whilst wearing plate (which gives 100% noise rating).
If you want to level your pick pocketing and stealth, go the infirmary at the Monestary. The wounded don’t react even if you fail.
If you have plate you can steal from country folk like charcoal burners and they will run away if they catch you. Then come back like nothing happened. No guards, but you will take a big hit on reputation. So im currently looking for a place like this near a town i dont care about
Even better. Do you get negatives reputation if you fail?
The issue with pickpocketing is the almost entirely RNG nature. You literally just hold E and pray.
Use lullaby potions in cauldrons and wait for the npcs to fall asleep, that’s what I like to do.
Or, You could actually ask the miller for more practice, which levels you up, until you are lvl 4 or 5 then go out and do some pickpocketing on sleeping people, which is easier.
get a grip and learn the systems they are not that hard.
Pickpocketing is another one of those features that warhorse plans to polish. You’re not alone.
It is somewhat tedious.
Youre right. Certain things i love and will go out of my way to figure it out. Pickpocket i dont necessarily love, so i didnt think of amazing ideas like this
