What is the best way to improve pickpocketing?

Question

Every time I have tried to pickpocket from someone, they realise what I am doing and I get caught. I sneak up to them and only attempt the pickpocket when I am undetected, but as soon as I lift anything out of their pockets, I get caught. Am I doing something wrong or am I just not good enough at it yet?

Answer 1

I used to level pickpocket, sneak and speech at the same by trying to steal from guards. Just sneak behind them for a bit, then pickpocket an easy item and repeat until you get caught. Now just opt to persuade them. Once your spech is high enough to persuade, you will be able to do this exactly once for each guard. They will however remember you and arrest you when you try to steal again from that exact guard.

Also if you're heavily into pickpocket, I'd recommend a mod to increase the maximum chance to 100%. In vanilla state, Skyrim caps the maxium chance at 95%, which will leave you getting into problems regularly even as a pickpocketing master. There are plenty mods available to achieve this, I'd recommend this one as it does just that and nothing else.

Answer 2

You are doing things correctly. Your chance of being detected while pickpocketing will be displayed at the bottom of the screen. The UESP has this to say on pickpocketing mechanics and leveling:

The chance of successfully pickpocketing an item is dependent upon the item being stolen. Heavier items and more valuable items are harder to steal but reward more exp for leveling. Most of the time stealing items worth more than 100 at earlier skill level and 500+ later on guarantee skill level increase. If you fail, the target will detect you and you will receive a bounty. Even if successful, there is also a chance that the target will hire a thug to kill you.

A possible way to exploit leveling is when you unlocked the Torture Chamber, reverse pickpocket everything you have on one victim, and then pickpocket it back. Of course, pay attention that at a low level heavier items can't be placed so stick with the lighter ones to begin with. Another method is to steal and reverse pickpocket gold with Sibbi Black-Briar in Riften Jail.

After investing in the Poisoned perk you may reverse-pickpocket poisons onto targets to damage them. Giving multiple poisons to a target will make them "take" the poisons until they are either all gone or the target dies. Remaining poisons will be left on the corpse.

An easy method for leveling any given skill plus pickpocket is to find a trainer, level as many times as your gold will allow, and then pickpocket the gold that was just spent. This may require several reload attempts or may be impossible to perform when receiving higher level training due to the large sums of gold required. The cutpurse perk helps greatly but does not assure success. Training one level and stealing the money back immediately will increase the pickpocket odds by keeping the amount of gold down. The sleeping Companions in Jorrvaskr and the trainers in the College of Winterhold are excellent targets to swiftly level up pickpocket and the skill they train in.

Answer 3

If you join the Thieves' Guild you can try to pickpocket its members. If you happen to get caught, they look away and do nothing.

Answer 4

I gained 50 pick pocketing levels in half a day by doing this:

Only works on guards... also you have to gain some king of respect that applies to the area your in. For example, pick pocketing in Riften using this method means first joining the thieves guild. For me, everywhere else was fine because I've completed the Stormcloak quest first. Basically, you can't get away with bribing thievery unless your a local "someone" to the guard.

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Steal everything they have that's easy enough, like 90%, if your lucky enough not to get caught, re-place it on them, and anything else you stole and don't care about. Keep giving and taking items until your caught.

When they catch you bribe them.. In my experience, they all demand 420 septims (ish), except for the Riften area, where it's only 12 septims. When this happens, wait for "HIDDEN" to appear and take back the money you bribed.

I've never been caught taking back the money... DO NOT carry on taking items after this. If your caught after bribing there's no option to bribe again. Only hit each guard once, I THINK after a period of time you might be able to hit the guard again.. Do so at your own risk, and by period of time I mean at least a few days.

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I did this to all guards in Markarth, Whiterun, Riften, and a couple of other places. Meanwhile, pickpocket every civilian, but only take things like money, lock picks or arrows, seriously. After a pick or 2 I'd stop, they seem to catch me even with 100 PP, and there's never a bribe option. If a guard is near by and says "stop!" then the fight stops. Attacking the civilian is a bad idea, and the guard is only handy if you can bribe them.

Hope this helps!!!

Answer 5

Join the thieves guild and either level up pickpocketing from one of the guys there or go around pick pocketing the members of the guild. They won't try to fight you and it leveled me up from 20 to 50 within minutes.

Answer 6

I found a good way to pickpocket. Go to a shop with an upstairs room, hide behind the door and when the shop owner comes up and opens the door you can pickpocket them from out of sight. Even while doing it this way you need to follow the basics others have laid out though: only steal high percentage items and save often when successful.

Answer 7

If you join the Thieves' Guild and buy a pickpocketing ring, your chance of succeeding is doubled. So just keep on practicing.