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I'm doing the Bedlam Job in Windhelm, and I think I should be done by now. I've stolen in excess of 1500 gold, mostly in jewellery, by pickpocketing in and around Windhelm, and the quest hasn't updated yet. I have successfully done this in other cities before.

Does "500 gold in goods" refer to the raw value of the items, or the amount I'd get from selling them to a fence? If that's not the problem, is this a known bug?

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The total value of the goods should be 500 (the raw value), not what the fences will pay.

Interestingly, if you do a sweep job in the same city, those items will count (and they're usually pretty valuable) even though you can't tell how much they're worth.

Here is a note from the UESP entry that may be of interest to you:

Note, stealing from the various NPCs and locations in the city may not work. Much of the time, to advance the quest, one must steal from the Keep of the the specified city, rather than its inhabitants.

As a last resort, if you are playing on the PC, you can finish it via this command:

setstage TGRNT 200

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    OK, I went to the keep and finished very quickly indeed once I found the room full of expensive alchemy ingredients. I stole a few things from stores, but probably not enough. Thanks!
    – andronikus
    Dec 8, 2011 at 22:40
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    On a similar note - I have been able to steal from the homes and businesses in town but pickpocketing has never worked for the bedlam jobs - at least for me.
    – spugsley
    Dec 8, 2011 at 23:36
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Goods obtained from pickpocketing don't count toward the total of 500

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Try telling any followers to "wait here" out of sight from where you take Items from. Also try the keeps. I had this problem in Solitude at the Blue Palace, so I reloaded from entering the Palace and told Lydia to wait by the door, then I stole the exact same objects and got the update. I havent tried a second time yet but I will update if it doesnt work.

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