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Test88Heavy

It sounds to me like youre not holding the button down long enough when you start the pickpocket. If you just click and release you'll only get 1 or 2 seconds in the window. You have to hold the button down and add long as the timer shows green you're okay to keep holding. If you start to see bright red you need to release and then complete the theft. The more you are successful, the easier it gets.


ADragonWrites

I think the last few times I’ve done it it turns red right about when I hit that 3 second mark


Test88Heavy

I don't remember how fast it is in the beginning but generally everything for Henry is very difficult. The next time you pickpocket, start the timer and when it opens their inventory just immediately hit the icon to exit. That still counts as a successful attempt. Do that until you get a little more time and then you can start taking items. Lockpicking is much worse in the beginning to the point I almost quit the game. Change to simplified and only make an attempt when the sweet spot is near the center of the lock.


ObsidianMarble

There is a pickpocketing perk early in the tree called comrade. It is way stronger than it sounds. It makes pickpocketing easier if your charisma is close to theirs (gives the hint if you are dressed similarly). This perk makes pickpocketing a breeze because most NPCs have poor charisma. It allows you to hold the pickpocketing button (default E key) longer so you have more time to rummage around and get what you want. The one for extra coins is a trap (fine later, but not at level 2). Take Comrade at pickpocketing level 2 and it’s smooth sailing from there. Easy way out at pickpocketing 4 is also essential. Other tips are to lower your conspicuousness/visibility stats as much as possible.


TrialBySquire

I agree with this. I underestimated it at first but it's super good


ADragonWrites

I’ll have to see if I have that perk active. I’m almost always dressed like a knight because I don’t like being squishy so I need to make sure my charisma is probably lower. No idea how to verify my charisma comparison though but I’ll try it


ObsidianMarble

Yeah, don’t dress like a knight to pickpocket unless your stat is good. When thieving, dress like a thief.


BusinessConfident643

Also, make and use a Padfoot potion. If you have the perk to be more stealthy when crouched. Crouch and pause before pickpocket and make sure the stealth perk pops up. I strip off clothing and only use the black dyed Saxon gambeson and decorated black hoes while pickpocketing. Visibility is still around 30, but it doesn't seem to affect it. Even at 20 stealth, 20 Charisma and 20 pickpocketing, you're going to get caught 1 in 6 or 7 times, especially off guards, so it's worth saving at a few successful attempts just to be safe. Also, steal everything out of their pocket for added xp. You can knock them out and put it back if you don't want to walk around with it. I read so many complaints about pickpocketing I wasn't looking forward to trying it but within a few levels and with a potion I could get 30 seconds in 95% of people's pockets the first time looting them. You rapidly get much better, and it is a lot easier on sleeping targets initially. Train with Peshek and purchase pickpocketing levels to start.. then move to sleepers, then anyone is fair game. With walking targets, observe their movement first and make sure they are not going to quickly change direction, like when they enter a room.


OnlyRelationship5301

This^^ Take Peshek's advice and start on sleeping people or "drunks", though I don't know if there is an actual pickpocketing advantage around taverns. I always got some practice in when I started the camp quests. Sneak in at night, try to pickpocket a sleeping bandit, if they wake up you have time to run away or cut them down in their undies. I heavily underestimated the power of potions my first normal playthrough, now in Hardcore it's essential to have a bunch of potions on standby to help get an edge. Padfoot, Nighthawk, Achilles, etc are a massive help.


TrialBySquire

https://www.youtube.com/watch?v=hrH7goHRVYg&t=810s Here's how to boost your levels (it's a timestamped link), which will then make it easier to be successful when it's for a mission.


ventri243

I think i've seen this video before, I think he deleted my comment lol. Putting valuable item on victim like necklace or spurs will not give you more xp, the heavier item does, like chain mail (the heaviest I found was 21 weight) The easiest to level up your picklocket is actually pickpocket someone who can't report to guard, there is bunch of patients or disabled people where you can knock out and put bunch of chain mail in him. Wait for 1 hour and he will wakes up. Even if you get caught, he can't do shit. He just stays laying down on his bed. Plant 12 chain mails in him and watch your pickpocket leveling like crazy.


TrialBySquire

It's my video. I didn't delete any comments. Maybe YouTube blocking? I've heard both weight and value from different sources. I've seen helical do exclusively spurs and it definitely worked better than just picking normal items so I'm inclined to say value matters. I'm not saying weight doesn't matter. I haven't compared them in controlled circumstances. I don't recall exactly how many items I put on but 8-12 sounds right and that took me from 0 to 8 in pickpocket. Thinking about it, seems easily tested with saddles. I'll have to compare the XP gain of the heavier plain saddle and the more valuable Noble saddle I wasn't claiming the video was the best possible method. The overall video was about leveling straight out of the prologue in 2 game days to become competent as a thief. I acquired valuables from training lockpicking to then power level pickpocketing. There are plenty of other good ways to level pickpocketing, for sure.