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I was doing the side quest "Caught in the Hunt", and during what was supposed to be the climactic battle I ran away. I got out of the guy's line of sight by going back into the tunnels under the castle and used my sneak skill to avoid him until he stopped looking for me. Once he was out of combat mode I managed to sneak up on him and (spoiler)

Spoiler

I pickpocketed the Real Fort Grief Key off him. I opened the gate and went back to Bravil to give Aleron's wife the bad news, but I still only had the dialog options to tell her he'd been kidnapped and ask about the Axe. So, I went back to Fort Grief under cover of darkness, got a sweet sneak attack on Dragol and managed to kill him. Apparently the trigger for the next quest stage is taking the real key from his body, but of course when I searched his body there was no key because I already had it.

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Obviously I could fix this with a console command on the PC, but any ideas on how to move things along on the 360. (I play on both, but I don't have Shivering Isles on the PC yet so recently I've mostly been playing on 360).

Hmm, this one must be a real puzzler as there haven't been any suggestions in a month, hopefully I'm not being rude or violating forum rules by bumping the thread...

After a month, I don't think you can consider it bumping the thread.

Not that I know of a solution, other than to reload that is, but Oblivion has a very tricky trigger system. Most of the problems here stem from people finding a quick way around a sticky situation and in the process making the triggers misfire, or not fire at all. Since you are using the Xbox, the only way would be to reload as there are no console commands.