I foolish took a pickpocket quest from the thieves guild that requires me to steal a diamond but I have a 0% chance to do so. Is there a quick way to grind up pickpocketing like the iron dagger strategy for blacksmithing?

Your best bet is to try to pickpocket jewelry since it weighs little but its value increases the skill faster. If you have trouble with that, lockpicks are almost a sure thing to pickpocket but are worth very little.

If you can somehow paralyze your victim, the moment an NPC is getting up makes them vulnerable to pickpocketing. There are also potions and gear to fortify pickpocket.

You may find this helpful: http://www.uesp.net/wiki/Skyrim:Pickpocket

Pay a skill trainer for Pickpocketing then Pickpocket the money back.

I did it by pickpocketing rings off of people all around the city. Almost everyone has a ring or an amulet on them that you can loot.

Reverse pickpocket somebody about 100 gold, exit pickpocket, save, pickpocket gold. If successful, repeat. If failed, reload. You can grind up to 100 very easily doing that - and if you invest perks into the field, you can gradually increase the amount of gold to make it go quicker. Once you get around 90% success rate for stealing the gold, I did it around three to six times before I saved, as that was the amount of times I needed to do it to gain a rank towards the end.

I'm not sure if you could do this but couldn't you take a follower with you, order him/her to stay at one spot and then pickpocket an item off of them.

Enchant your equipment with 100% lockpicking... then pickpocket whatever...

Whoa!
I never took that into mind. I always blindly went after the big stuff and always got caught.

Thanks for the heads-up, you just helped me grow some sticky fingers.

You can safely abandon those sidejobs from Vex and Dev. They'll complain and moan, but nothing will come of it.

My 'completed Thieves Guild quests'-statistics is at -23

How do you abandon a quest?

This guide assumes you have low skill level in atleast one school of magic and low level in pickpocketing.

1. Enchant a Fortify Pickpocket item if your pickpocket skill is below 35. Else you may be doing alot of loading.
2. Go to Collage of winterhold.
3. Wait until everyone is asleep.
4. Quicksave (F5)
5. Pickpocket any one of the teachers. Take only gold. Quickload if caught (F9)
6. Ask to train any School of magic once.
7. Repeat step 4 to step 6, until you used up all 5 trainer points of the level.

The combined leveling of pickpocket skill and magic should have leveled you. Level up and continue from step 4.

If you used up all trainer points before leveling, pickpocket the rest of the stuff from any of the sleeping people around.

Should the magic skill you have been training reach 51 level and the next upgrade costs 1500 gold, STOP. Switch to another victim.

If you do have the pickpocket enchantment, you may want to train the enchantment school. That let's you enchant more powerful pieces of equipment (from stolen soul gems around the collage) to steal larger amounts of money easier and reduce the number of reloads you have you do.

With this, it is possible to level multiple schools of magic to 50 and pickpocket to 100. However you will find yourself over leveled and combat may become dangerously differcult if playing above adept difficulty.

Tell Vex or Dev that you want out of the job. Those sidejobs are the only quests in the game that you can abandon though.

I went to guard barracks at night and pick-pocketed them while they slept. It was a little tedious, saving after each guard, but you can pick a dozen pockets at once in some of the barracks.

The courts of all the Jarls are excellent locations to practice pickpocketing. Also the taverns and inns, but the loot is usually not quite as good.

Using ^^ and 'save' / 'load' are the best bets Gems are also light and have a high associated value to them.


I read this but I never found a trainer to pick pocket from... but sounds valid also

i wore anything pickpockety fortify that i owned (eg ring, boots), went to Windhelm, Palace of Kings, and worked my way around the table, going in circles. Save after every 2/3 pickpockets incase you get caught.

Great tips. I just want to get to the "Extra Pockets" perk, but i can see myself having some fun with a higher pick pocket level.

I just pickpocketed jewelery around each town. If I got caught then a guard would come and take all the stolen goods, but I could bribe them to leave me alone. Then you just pickpocket your gold back from the guard.
It levels up pickpocketing really quick without having to worry about what to do with stolen goods.

there is a begger in Windhelm called something the unseen. she is a trainer in pickpocket.

Pickpocketing is fun and easy once you put some points into it. First off, it helps to pick a race that has at least +5 to pickpocketing. This will enable you to get started on the perks immediately. That first 10% bonus sounds trivial but trust you me it makes a big difference. Quick safe after each successful attempt. Reload when you fail. As your skill increase go for heavier items as it gives more xp. My thief has 100 pickpocketing and it's great fun to steal everyone's clothes right of their bodies. Of course stealing their weapons and then starting a fight are some of the best moments I have as a thief.

i can just imagine the person standing there almost naked, weaponless and angry as hell. love the idea.

What do you mean "almost" naked? Not with the right mods. Lol.

not on pc so almost naked is as far as she is willing to go. LOL

There was a cheesy way (dunno if it was patched) to get it high. If your sneak is already super high, say 100 with all the perks, then you can let yourself get caught in Riften. Or there is a guy in the Riften jail. He is behind bars and you can gather up objects from the jail and give them to him and take them over and over, periodically walking a loop to avoid a patrolling guard, but it only works if your sneak is super high. The reason this works is that the guy in jail cant report you since you are already in jail, and he cant attack you. So as long as the guards dont see you, you can just do it over and over.

Its most likely an exploit, in that it probably didnt occur to the devs that no repercussions means endless practice. But I figured i'd let you decide for yourself. And I have no idea if it was patched. I'm still playing on patch 1.1 in offline mode, since I never wanted the bugged 1.2, and havent gone back online to try any subsequent patches.

Get to the work and start pick pocketing.

I would start with sleeping people, and the place for this is barracks.

Go to the Whiterun barracks for starters, and pick pocket the sleeping people, then the sitting ones, and then the standing ones.

I would steal the items that I can use right away, like money, arrows, lockpicks (and it is interesting how all the guards have one at least), and then go for the pricy but weightless items like rings and amulets.

Those pricy items are great for increasing the skill and also after one barrack, I will never need to buy any steel arrows for the rest of my carrier.