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IIRC you should receive the letter from a courier to start it once you join one of the two sides and complete the first Hold invasion quest.
I think…I know it only begins once you’re through the first two or three quests of your civil war faction’s questline. But I’m pretty sure you get it BEFORE the Battle of Whiterun.
Even if you have before, go in and come back out.
Now that I’m remembering it more, there’s sometimes a weird glitch where the courier won’t show up unless you’ve been in the Drunken Huntsman before or recently. I think I had to go in there and exit in order to get him to spawn.
If you have not joined either side of the CW, the letter you’re referring to can be found inside the DH. You then either go to the Imperial or Stormcloak NPC and must perform some favor for them to prove you’re worthy of representing them in the battle.
If you join one of the sides (but do not grab the letter from the DH beforehand), you will eventually get a letter from your chosen side’s NPC. You go to them, talk about it, and then grab the new armor and head to the battle site.
I can confirm this because this is how it happened for me. I joined the Legion and kept wondering why I had not gotten the quest yet despite nearly being at The Battle of Whiterun. The Legion NPC who gives it to you was even there in Castle Dour but he would not talk to me.
I then searched for an answer as to why and found the suggestion to enter and exit the DH.
As soon as I exited the DH, a courier spawned and ran up to me to give me the letter starting the quest.