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I understand that there is the possibility of the Stormcloaks capturing a hold, or city, such as Whiterun. Is it possible to be both the Thane of a Imperial controlled hold and a Stormcloak Hold, if you are allied with neither faction?

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Interestingly, I was named Thane in Whiterun both under Imperial and Stormcloak rule. As a result, I know have both the Axe and Sword of Whiterun hanging in one of my weapons racks. –  Iszi Dec 24 '11 at 3:22

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Yes.

The only Hold which you cannot become thane of without choosing sides in the Civil War is Windhelm. You must resolve the Civil War, one way or the other, to be named Thane in Eastmarch.

Other than that, you can become Thane of any hold by doing other quests, unrelated to the Civil War, or by advancing the Civil War to a point where control of the hold in question changes hands, at which point, you will be offered Thaneship automatically.

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Once the war ends, its a different matter. Go to all holds where you were Thane and depending which Jarl was removed from his Jarlship then re-become Thane again by talking to the new Jarl. –  ヴァイシャリ Oct 18 '12 at 16:34

In Whiterun, if you become thane before resolving the civil war and then join the Stormcloaks, you have to talk to the new jarl about becoming thane again. All you have to do is have the house; you don't have to help people.

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-1 This does not answer the OPs question. The question was Is it possible to be both the Thane of a Imperial controlled hold and a Stormcloak Hold, if you are allied with neither faction? –  ヴァイシャリ Oct 18 '12 at 16:38

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