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Certain radiant quests have brought me to the same area on occasion. A good example would be the Redwood Redoubt, of which I've been contracted to the kill the bandit leader three times now. And though I'm fond of murdering bandits, I'm more fond of stealing their treasure so if there isn't any more for me to take, I don't see the point in questing in that area again.

That said, do the chests and other containers (burial urns, cabinets, bookshelves, etc) in a dungeon ever respawn their contents? If so, any idea how long this process takes?

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Were the chests restocked on your three separate trips to Redwood Redoubt? – Raven Dreamer♦ Dec 7 '11 at 22:08
@RavenDreamer No but they were in pretty close succession to one another. I was just trying to make some easy gold and just kept getting this quest – spugsley Dec 7 '11 at 22:10

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I can confirm that some will eventually respawn, though I'm not sure how long it might take.

What won't happen is the locations ever changing from "cleared" ; the chest in question was the dragon loot chest by the word wall in Dragontooth Crater, near Markarth. The chest had gold in it, which was a dead giveaway that I hadn't "partially" looted the chest earlier and forgotten about it. Despite the location being listed as "cleared", I had to fight another dragon to get to it.

It's not clear (and probably won't be until January w/ the Construction Kit) which chests won't respawn ever -- but in the meantime, I can verify that at least some do.

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