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So I was simply taking some weight off an NPC when he caught me... helping lighten his load. The problem is, he still has some stuff that I am sure he would rather have me hold on to but he has "already caught me" and won't let me hold onto any more of his stuff.

Is there a time after someone has caught you pick-pocketing where the option to pick-pocket them becomes available or will you never be able to steal from that individual again?

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You will eventually be able to pick-pocket that NPC again, yes. Not making this an answer because I don't know what conditions are required to reset this condition, I only know that I've gotten caught and later successfully pick-pocketed the same dude. –  Kromey Dec 6 '11 at 2:17
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I'm pretty sure if you just leave the area (loading screen) and come back you'll be able to try again. Can't be bothered to test it though. –  Mr Smooth Dec 6 '11 at 7:33
    
Epic Wording of the Question! Upvote. –  Ender Dec 6 '11 at 10:46
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up vote 6 down vote accepted

So I tested @Mr Smooth's recommendation and it is indeed true.

If you have been caught, then you need to trigger a load* by doing a large zone transition. A small one (such as going from the ragged flagoon to the ratway) was not enough to cause the flag to be reset. However, transitioning from the cistern to Solitude was enough to cause the reset and I was able to immediately attempt to steal again.

In short, if you are in a town with a gate, then exit the town and go back in. Simply going into a house in the town is probably not enough to reset the flag. If you are not in a gated town, just fast travel to somewhere far enough that requires a load.

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Help me no matter what i do it wont let me pick pollcket raerek for the stormcloak quest Ive traveled far away and came back but it still said i was already caught –  user19054 Jan 28 '12 at 4:03
    
@Michael did you travel far enough away for a loading screen? –  z - Jan 28 '12 at 14:28
    
Traveling from Riften to Solitude takes quite a while, I think the real factor is the passage of time, not loading screens. –  kotekzot Feb 21 '12 at 3:17
    
@kotekzot wrong, if it is the passage of time then waiting for 5 days in the same zone would reset the flag, but it does not –  z - Feb 21 '12 at 11:52
    
@yx., yeah, you're right, I misspoke, it's the passage of time coupled with at least 1 loading screen. What I am contesting is that the distance traveled is a factor. –  kotekzot Feb 21 '12 at 12:04
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Additionally if your pickpocketing attempt on someone has failed, then you can no longer pickpocket anyone else in that city if you have ever failed to pickpocket them previously.

I found this out when I was doing a job for the Thieves Guild. When one of my pickpocketing attempts failed, I literally was not allowed to pickpocket anyone else in the city. I'm not completely sure if this will hold true for all of you, or maybe it was just a glitch, but I'm just telling you this on self-experience.

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How much was your Pickpocket skill? –  ヴァイシャリ Nov 8 '12 at 17:45
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Yes, you can, but you have to leave the place you are and wait a full day before coming back.

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