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Background

You'll receive this quest from Astrid in the Dark Brotherhood Sanctuary immediately after completing the quest Bound Until Death.


Walkthrough

Astrid will direct you to Gabriella (also in the sanctuary), who will give you the details for your second assassination contract for Amaund Motierre. Gabriella will tell you that Commander Maro of the Penitus Oculatus Outpost in Dragon Bridge is in charge of the Emperor's security in Skyrim, and that to distract him from doing his job, you'll need to kill his son Gaius and plant evidence on him implicating him in an assassination attempt against the Emperor. For a bonus, you'll need to complete this task while you're in one of the major cities, where Gaius (and the false evidence) will be found more quickly.

The first thing you should do is head over to Dragon Bridge, which is located on the western side of Skyrim near Solitude. When you get there, you'll witness Gaius bidding farewell to his father and his girlfriend, and then he'll start his long trek around Skyrim. If you duck into the Penitus Oculatus Outpost and steal Gaius Maro's Schedule (easiest to do when Commander Maro is still outside), then you'll discover Gaius' route -- Solitude to Windhelm to Riften to Whiterun to Markarth -- which he'll repeat until you've completed the quest. You'll need to kill Gaius in one of those cities in order to collect the bonus.

The easiest way to deal with Gaius is to talk to him and say, "After I kill you, I'm going to kill the Emperor." This will cause him to attack you, which will allow you to defend yourself and kill him without recrimination. Failing that, you'll need to follow him around and kill him when nobody is looking. The best place for this is in Whiterun when he's staying in a private room at the Bannered Mare. In the other cities, Gaius will hang out in castles and guard barracks, which will usually be crowded. Once you've killed Gaius, you'll just need to place the Incriminating Letter into his inventory to complete the contract.

Note: Gaius will drop Penitus Oculatus Armor, Penitus Oculatus Boots, Penitus Oculatus Bracers, and a Penitus Oculatus Helmet when he dies.

When you return to Gabriella, she'll reward you with some gold, plus Olava's Token if you managed to kill Gaius in one of the five cities. The token will allow you to receive a reading from Olava the Feeble in Whiterun, which will lead to you to Hag's End, where you'll find Ancient Shrouded Armor, Ancient Shrouded Boots, an Ancient Shrouded Cowl, and Ancient Shrouded Gloves.