Quote Originally Posted by Grim Portent View Post
Probably, as I understand it Skyrim's development wasn't exactly smooth. Stuff being put somewhere in an early draft or storyboard and then not being there in the actual game seems quite plausible to me.
From a Doylist point of view it sounds like the two dialogues, the one in the opening scene referencing crossing the border and the one later on that references Darkwater Crossing, were written by different people who had limited knowledge of what the other side was doing then. The part about crossing the border makes more sense with the physical location the opening scene takes place in, which the writer probably knew, but the other writer either had no idea about the circumstances of the Imperial ambush, or had no idea where Darkwater Crossing was supposed to be and somehow thought it was in that area of the border. Because yeah, trying to put the two together makes zero sense.

Ignoring the whole border business and focusing just on the Darkwater Crossing ambush makes some sense with Ulfric's movements, since it's on the way from Riften to Windhelm (and doesn't require answering the question of what the hell was the leader of an insurgent faction doing outside of Skyrim), but as you said above, it makes no sense at all with the logistics of moving the convoy all the way to Helgen. And, if you throw out the "trying to cross the border" thing, as flimsy as that is, it leaves us with no explanation of why the Dragonborn was captured...