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So I wanted to reverse-pickpocket daedric arrows that I just obtained onto some bandits. That would allow me to collect these arrows as they shoot them at me. However whenever I try to pickpocket on any of the bandits, I get a message: "Bandit has already caught you pickpocketing." There are few things to note regarding this:

  • My pickpocketing level is 100
  • I did not any time recently pickpocket any bandits.
  • The bandits that I tried it on were recently respawned, I remember cleaning that camp.

So what is exactly going on and how to fix it?

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If this Bandit truly just spawned, then this is a reported bug. From the UESP page on Pickpocketing:

On rare occasions, you may be unable to pickpocket any NPC in an area with no clear cause, instead receiving the message you normally see when trying to pickpocket someone who has already caught you. Waiting 48 hours in a different location seems to fix this issue.

Thus, if you really want to Pickpocket this particular Bandit, it looks like you can just go someplace else, wait for 2 full days, then come back and reverse-pickpocket them.

0

Not directly answering your question, but an alternative approach to getting more arrows, how about reverse-pickpocketing the arrows into the pockets of the guard practicing archery in Solitude? You might need to remove all his other arrows first, but with those skills that shouldn't be a struggle. Just give him one and he'll shoot lots of copies into the targets there...

  • I did that, it's too slow. – Tomáš Zato Jan 17 '17 at 17:53

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