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The Elder Scrolls V: Skyrim Hints
Find the Imperial Courier.
1 of 4: Go to the inn in either Dragon Bridge (a ways SW of Solitude) or Rorikstead (a long way south of Dragon Bridge).
2 of 4: In either place, talk to the innkeeper and ask about Imperial couriers.
3 of 4: Try passing the persuade and intimidate checks first. If neither works, use the bribe option. Any of those will get you the next objective.
4 of 4: NOTE: Instead of using the bribe option, you could wait in whichever inn you're in for the courier to arrive. That'll also get you the next objective.