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What is the best way to improve pickpocketing?

So i have done lots and lots of research on how to level pickpocket fast, but im already a level 90 so im not going to pay the outrageous price to be trained, and i dont really want to spend like an hour just going around pickpocketing people, so are there any faster ways to level up pickpocket once im already 90?

  • 1
    No because hes just asking how to keep from being caught pickpocketing, im just asking how to keep leveling when the going gets tough Mar 28, 2012 at 13:41
  • 2
    He does not ask how to prevent being caught. He asks how to improve because he is getting caught.
    – user9983
    Mar 28, 2012 at 14:22
  • 1
    Master level trainers go only up to level 90. Even if you have the money, you cannot get training beyond 90.
    – Anderson
    Mar 28, 2012 at 18:18
  • Pickpocket is the only skill you can train to100 Mar 28, 2012 at 21:52

1 Answer 1


I found this pretty easy to do with a follower, such as Lydia. Ask her to take something expensive, but light weight (ie, a ring or necklace). Then steal it back from her. In my experience, if I failed I didn't get a bounty, but your mileage may vary. (Lydia tended to just say something to the effect of "I saw you, but I'll let it go... this time")

If you fail, I think you have to wait 2 days before you can steal again, which means that quicksaving/loading is probably faster.

You can also level this easily with skill trainers, as money paid to them for skill training ends up in their inventory. Pay them to rank up a skill, and then pickpocket the gold back. Some skill trainers are also followers (the Companions come to mind immediately), so you can do a little of both if you so desire.

The only downsides to this is that you can only train 5 times per level, and that it's relatively easy to end up with the trainer carrying too much gold for you to feasibly pickpocket. If they're following you, though, you can always take the money back out of their inventory if you get stuck in this situation.

Keep in mind that skill gains are based on the value of the item, whereas the difficulty is a combination of weight and value. Therefore, light but expensive things provide the best balance of skill gain to risk.


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