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I've been trying to pickpocket because that is one of my favorite things but it seems I can never get close enough because I get spotted any tips would surly help!
Some targets are easier than others. It is really hard in high traffic or crowded areas unless you have potions of invisibility. If I can't get the eye to close while being right behind someone because other people are able to see me I just move to another target until I find a good one. I can usually find several easy marks in a city like Mournhold or Wayrest.
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Pick a target where there isn't a chance of another NPC coming by and seeing you. Approach directly behind to stay out of their line of sight. Wait for the ding and the bonus chance to pick their pocket successfully.
Also you cant take long to pickpocket. If you are passing by someone your chance for a moment greatly increases, to lower down again if you stop. You should be able to see this moment. So its best to pickpocket fast.
Level up your legerdemain skill and put points into the pickpocket passive. With the passive maxed, pocket picking becomes ridiculously easy. You'll have 100% chance to pick all NPC except Hard, where the chance is 90%. I'm working on 1000 pockets picked achievement, regularly pick Justice guards without getting caught. Use the techniques listed above.
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