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Skyrim Tips – How to Level Your Pickpocket Skill Fast and Easy

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How to Level your pickpocket skill fast – Skyrim

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There are a few easy ways to get a higher pickpocketing skill in record time. All it takes is a little ingenuity, and the desire to rob every living being in Skyrim blind. Here are the best tricks for leveling up this skill as fast as possible

  • The most basic method is to stand behind an NPC, quicksave, and attempt a pickpocket. If you succeed, save again, then pickpocket again. If you fail, load up your save, and then try again. It’s the most sluggish but most conventional way to level up, but there are far easier and faster ways.
  • During the Dark Brotherhood quest line, you’ll find yourself in a cabin with a bunch of tied up NPCs. This specific part of the quest is called “With Friends Like These…”, and it’s a great way to level up your pickpocket skill. Simply drop a high amount of gold into their inventory, then steal it back. Do this over and over, and don’t mind if you fail. These NPCs won’t be able to report you or attack you. For obvious, grim reasons.
  • You’ll get more experience for stealing items of higher value. Aim for high value, low weight steals like jewelry or gems for fast leveling.
  • Head to a pickpocketing trainer and pay them to level up this skill. Then pickpocket your money back, and pay them for even more training. Do this repeatedly for free and fast experience, though you will have to level up to continue to receive training.
  • Make your way through Skyrim’s Blood on the Ice quest. At one point, you’ll be able to sell a strange amulet to Calixto Corrium for 500 gold. You’ll then be able to steal it off him, and sell it to him again. This can be done over and over, though we recommend saving before you go digging around in his pockets.

With these tips, you’ll be a master pickpocketer in no time. Good luck!


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Image of Sharon Coone
Sharon Coone
Twinfinite's former Editor in Chief from 2014 to 2017. B.S. in Biology, B.A. in Philosophy, and always within 20 feet of a bagel. Kind of like a reverse restraining order, but with carbs. Sharon's love for video games knows no bounds, and could be found writing about anything and everything at all hours of the day.
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