I've always wondered how would the city of Bruma would fair during Skyrim's civil war. Being the closest city/county to Skyrim, I would imagine that the people there would pay more attention to the conflict than the rest of Cyrodiil. Which brings me some questions.

1: How would Ulfric's reputation stands in the Jeralls? Would most of the population like him? Dislike him? Not care? Or mixed?

2: Would there be civilians there so devoted to Ulfric's cause that they act as independent rebels fighting the Legion in the Jeralls?

3: How possible would it be for Stormcloaks sneaking into County Bruma using Guerrilla warfare to do things like disrupt what little supplies being shipped to Skyrim from Cyrodiil/ just making it harder for the Empire to support the Legion in Skyrim?

It's a good theory to think of, I think Bruma would have a lot of imperial support though seeing as it's a major city in Cyrodiil, but it's possible that the nordic culture there has the community split.

I'd imagine that the border would be pretty well guarded, and besides, the Stormcloaks are more interested in taking back Skyrim. While it would make sense to attack your enemies home property, it would probably be suicidal to leave your land and possibly get cut off by imperial forces already in Skyrim.

At least by sticking to Skyrim they would be able to have the "home-field advantage" and not risk an Imperial force sneaking up behind them.

AFTER the civil war though if the Stormcloaks were to win, then they could maybe make a jab at Bruma but it really depends on if they are after the Empire itself or just trying to take Skyrim and be content with that.

When I meant about Stormcloaks attacking Bruma, I didn't mean by large armies. Just that small units sneaking through the Mountains. (Pale Pass may be a major entry way to both provinces, but there should be smaller passes unknown to one side but to the other.) And would perform hit-and-run tactics for a little bit before returning to Skyrim to take a break, then repeat.

And there's another question that I forgot to put in the OP: Would there be an increases Legion presence in the region? Not just in Pale Pass but in the city itself and surrounding towns and villages?

Unlike Skyrim itself, Bruma sits nicely within Cyrodiil. Ulfric by an large doesn't want a full blown war with Cyrodiil on their own turf and would much prefer to get Skyrim united in the quickest fashion possible. While his uprising might be a act of war on the empires part, it seems to be mostly contained to its own boarders. For Bruma, a point of contingency there might be to restore its chapel, but there probably isn't any great need or pressure to make any overt moves in the city.

The Empire is seemingly trying to tighten its boarders all around. Not only is there more of a presence down by Dominion territory, the legion thinks its a good thing to secure Riften "just in case" something comes from Morrowind. They seem rather paranoid, but considering the circumstances, I can't blame them.

1: I see where you're coming from. I had forgotten about Ulfric saying that he would halt his army's advances just because Titus Mede II was in Solitude. But If Ulfric doesn't want to risk a full- blown war against Cyrodiil, (The Stormcloaks seemed to be having a hard time fighting just one legion in their own province. Just imagine if the Empire sent in several more.) then what about the residents in Bruma that could support the Stormcloaks? Could some of them form some kind of militia to fight the Legion?

2: I noticed that too. Don't know how the Empire can do that since they seemed to be stretched out though.

Culturally Bruma was already quite split in TES IV, with Nord residents commenting on snooty Heartlanders, invasive imperial cult attitudes, etc., and vice versa non-Nords either putting a positive or negative spin on the cultural divide. So I imagine that could end up being pretty hot, not just from the Skyrim civil war but from the Talos ban. The chapel in Bruma is was a Talos chapel and there's that cute statue of Hjalti which would probably also have to come down.

The biggest problem with the idea of hit and run tactics is that Bruma is a walled city. Maybe they could attack any houses surrounding the city, in reality there would be farmland and small residence outside of the walls, but otherwise there would be no attacking such a city and simply walking away to fight another day.

As for Bruma supporters of the Stormcloaks, why would they? Even if they are Nord's, the Stormcloak rebellion is centered on a free Skyrim and Bruma sits well within the empires and Cyrodiil's borders. Maybe there could be a small crowd of the residence that support the rebellion, but short of leaving Bruma and going all the way to Skyrim to fight, there isn't really much a group there could do unless it became a full scale uprising within the city itself.

Well the thing about the statue is it could be written off as being a monument to the man Tiber Septim so it could stay up but yea, the ban on Talos would effect Bruma the most because of the chapel.

1: I didn't mean that they would make hit-and-run attacks on the actual city. If the Stormcloaks were to do something like this, I'd imagine they would focus the raids on Legion outposts, convoys, or anything that could support the war effort in Skyrim.

2: We could take into account that many pro Ulfric Nords in Bruma might want to make the city a part of Skyrim, so they won't have to deal with the WGC. Now whether Ulfric will want to take Bruma from Cyrodiil or not is not really clear. He could gain popular support from "liberating" a mostly Nordic city that's a victim to a dreaded treaty. But he might not want to risk pissing Cyrodiil off even more than he already did.