Hi

I am a member of Imperial Legion, but I got this quest in Whiterun to save this Thorald Grey-Mane, who is a Stormcloak supporter, from Northwatch Keep that is guarded by Thalmor.

1). Can I run into trouble saving a Stormcloak supporter, when I am a member of Imperials myself? If yes, what are the consequences?

2). I can't seem to get into the Keep without Thalmor attacking me. If I kill them, will I get in trouble with them later in game? What are the consequences?

Skyrim and it's many quests confuse me. I can never figure out whether things are interconnected or if they are just random and arbitrary, without any form of punishment or consequence.

1. No.

2. I have not found any way to get him released without attacking the Thalmor guards, even after completing the imperial quest line. It might be bugged, but as of now I think you have to fight your way in. No consequences, nobody cares.

It seems that even if the objective is still there, the ability to negotiate a release was left out of the game.

The Imperial Decree to release Thorald cannot be obtained. If obtained, it cannot be shown to the guard because the dialogue is out of order. If that's fixed, he acknowledges it, but it does absolutely nothing. So there is no peaceful solution.

That doesn't necessarily mean that the quest is missing an option -- consider that if you pursue the would-be peaceful option, Alvustein and his friends will not accompany you, which may be preferred for stealth-based characters.

There are no repercussions with the Legion if you help, and no one cares if you kill all of the Thalmor, though you can minimize casualties by sneaking in the back entrance (you'll still have to kill pretty much everyone outside to avoid Thorald's death, though).

I appreciate the replies.
I start losing interest in this game, because there doesn't seem to be any purpose to anything, nor are there consequences for breaking the rules, which more or less don't exist in the first place.

Yet, every guard in the game will know about your exploit and will also comment about it!
I love the guards: they went from knowing about every crime committed everywhere in Oblivion, to knowing all the history of the Dragonboard, including secret exploits (being the head of the Dark Brotherhood, releasing Thorald from a forsaken fortress in the middle of a frozen wastland, etc...)

remember that as a member of the Imperial Legion the Thalmor are the enemy.

they want the imperial Legion to lose.

the only good Thalmor is a dead Thalmor.

Um. That's one interpretation. There's a similar interpretation from the Stormcloak angle. But your last statement IS spot on.

as a Skyrim character, Thalmor are desired to die.
only the pact allow them to walk alive in the land.

the end goal of the Thalmor is the enslavement or destruction of Tamriel.

the truce that was signed only bought Tamriel some time.

2: the empire hate the Thalmor and are biding there time so they probably wanted them dead, just my speculation hell im a Stormcloak suppporter but even if my character was up-there-anus empire suporter id still maim the Thalmor whenever the chance presented itself.

Missing in Action is a wonderful quest, especially for a sneaky-type. You get to creep around and back-stab or slit the throat of lots of Thalmor in order to release a lad from captivity and so make his mum very happy, and there is lots of loot. What is there not to like?

that i cant hang them outside the Embassy to make them realise thats there fate.

It's also a great quest for the 'I have a large axe and I'm going to split your head with it' type also.

It really doesn't matter if you are a Stormcloak supporter or not as many have already said, the Thalmor are the enemy. However, from a Role-playing point of view it makes great sense to do this if you are a Stormcloak supporter.

The Empire had just finished turning the tide of the war at the time of the Concordat. If you ask me, its the Thalmor who are getting all the benefit of the current peace. Absolutely abysmal strategic error executed by an aristocracy without the backbone to do what's necessary.

It's also a great quest for frying Thalmor alive in their armor while you fill the passageways with fireballs and lightning bolts.

I also think that quest is bugged. you can't get him out without killing thalmor guards at all, like someone mentioned, but even more realism breaking, after he exits the hold, the thalmor guards chase after the both of you for about 3 seconds and then they go right back to guarding the hold.... while the dude you rescued just stands there... i hate those "you're playing a bugged game" reminders.

Since not a single Thalmor is left alive once I'm done, I've never noticed.

No kidding.... I LOVE wiping that nest of Thalmor off the face of Nirn.

I'd think not seeing how I've almost completed the Stormcloak quests while wearing Imperial Armor the whole time and having the Imperial woman from the Windhelm dock as a follower.