Alright, so:

Kiralla x Gaela are currently being escorted by Guardsman Francis, carrying a written letter from the Archmage of Winterhold. It's up to you what it says as to the reason Kiralla and Gaela were supposedly sent to meet with the court mage. Feel free to try to get lost, even though you have a crude map of the halls.

Fiona x Faruq are permitted to meet with the Captain of the Guard to receive their payment and also to witness Brynn's trial and execution.

Cedric x Finch, you're equipped with spyglasses on the battlements, wearing pilfered uniforms. Try not to let the other guards look at you up close or they might not recognize the two of you as guardsmen. Guardsman Vendel can only cover your asses so much.

Maulakanth x Valen x Cyrendil, the sewers lead either to a deadly drop-off or to the dungeons. Who knows what you'll encounter lurking in those sewers. Just make sure you make it to the dungeons in a timely manner.