How can I improve my pickpocketing?

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.

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.

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!!!

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.

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.

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

Go to Dragon's Reach and pickpocket the guard by the door placing and removing items until you are caught. Persuade him to let you go and continue to do the same thing. When he catches you the second time, agree to pay the fine. This will place you right outside the door to Dragon's Reach. Go right back inside and start pickpocketing the same guard. He will eventually catch you again and draw his sword. However, he will not try to arrest you until you talk to him. Keep giving and taking items. Every time he catches you, your bounty will increase by 25 gold, but he will not arrest you. You can do this ad infinitum. P.S. Bring some very valuable items to use.

I leveled pickpocket to 100 in one day by finding a pickpocket trainer (e.g. Beggars), and continually training and pick-pocketing off of them, these is an extremely cheap and effective tactic as if you start at a low level you will literally be able to fly up to level 20 in no time at all.

It gets slightly more difficult as your pickpocket training becomes more and more expensive; as its harder to rob larger amounts of gold. best practice starting out is train once, pickpocket trainer , repeat. Then later on train one to three times pickpocket all the gold back, train twice and pickpocket the gold back.

Best of luck.

1. Quick-save.
2. Steal gold. (If none, see step 5.)
3. If caught, quick-load.
4. Quick-save.
5. Plant gold.
6. If caught, quick-load.
7. Repeat ad libitum.

It seems that the most efficient item to plant and/or nick is Gold. This is the main reason that I'm adding an answer when there are already many answers. I was following the advice that XP is gained by value, but I clearly gain levels much faster if I pickpocket 155 Gold at a time instead of a Weight 0.5, Value 412 Necklace of minor Stamina. I was wondering why it seemed that I was leveling much slower than I had the first play-through that I grinded Pickpocket. The amount of Gold still seems to proportionally correspond to XP earned per pickpocket.

When you get to the point that you have a 90% chance of succeeding and you don't want to quick-save after each pocket-pick, consider this math:

• First pickpocket attempt: 90% chance of not being detected.
• Second attempt: 90% * 90% = 81% chance.
• (3) Ans * .9 = .729
• (4) .6561
• (5) .59049
• (6) .531441
• (7) .4782969

If you are going to save-scum anyway, here is a mod that makes pickpocketing always successful. And here are some more mods:
Pickpocket success chance maximum 99% mod
Pickpocket success chance maximum 100% mod
Pickpocket success chance maximum 95%, 99%, or 100% mod
Pickpocket success chance minimum 1% mod
Extreme customization (SkyTweak)

I have no idea if anyone is going to need this any more, but I've found a much better way than anyone has mentioned so far. If you're early in the game, travel to Windhelm, find the young boy who's trying to summon the Dark Brotherhood, and complete the quest where you kill the old woman at the orphanage. Once you've done that, find a bed anywhere and rest, where you wake up in an abandoned cabin. Here, you have three people, all of who are tied and blindfolded: you're allowed to pickpocket them all, and as long as you don't leave the room, you can do this infinitely. Once you kill one of them, you can hide behind the Argonian, where you can become hidden. This makes it easier and quicker to judge when to pickpocket, as your chance of success is much higher when hidden.

To speed things up, I placed all my heavy items in the chest in the room as well, since lighter items have a better chance of being successful, so that I could just spam 'X' (I'm on Ps3). I also raise my conjuration skill by using soul trap on them, and then once I'm hidden again, go back to pickpocketing until my magicka is high enough again. It's cheap, but I can guarantee that there is no faster way. It gets much easier once you start unlocking abilities on the pickpocket skill tree.

You can go up to the person who trains in the pickpocketing skill and train then steal/take back your money and keep going. Don't worry about being caught since anyone in the guild is peaceful and will not attack when you pickpocket. Also go to the smith in whiterun(only work if in the companions) and pickpocket him taking and giving the same items. The smith is the one in Skyforge.

Found the best pick pocket trainer ever! Found a courier standing around and proceeded to pickpocket/reverse pick pocket him. If he catches you he will run but will NOT call the guards. Just hide and give him a moment once it says you are hidden he will return to the same spot and repeat! Upgrades sneak and pickpocket with no worry of getting caught!

One good method is to Fus Ro Dah a guard. Then while they're getting up, pickpocket them. Now since they're getting up, they won't catch you pickpocketing, even if the item is 0% chance to steal. Pickpocket all the items the guard has and place your items in it. Then take it back. repeat this to improve the skill.

Why did no one thought of pickpocketing bandits/enemies?

Go into any bandit/farsworn/wild mages/any pickpocketable enemies hideout at night, some if not all of them might be sleeping - easier to sneak and better chances to pickpocket. Plus if they caught you instead of a bounty and guards chasing you all over you just need to win that one fight and you are free to go.

Most of these enemies also tend to carry some light/low value items that make early game levelling easy - such as a few coins or potatoes(cheap foodstuff). And if you are proficient and lucky they might also carry valuable gems and equipments(might need perks for this). If that all is not enough pickpocket training, after emptying their inventory you can reverse pickpocket a bottle of poison - maybe more for higher level targets, to both increase your pickpocket level and finish the target off without a fight.

Dark Brotherhood quest "With Friends Like these". The captives are a great way to level your pickpocket skills. If you crouch behind one and become undetected, load and unload items into their pockets. Get caught? No worries, you don't get a bounty for obvious reasons. Rinse and repeat for a steady climb in skill points.