- Speak to Astrid.
- Find Cicero’s journal and take it to Astrid.
- Mount Astrid’s horse, Shadowmere.
- Ride to the abandoned Brotherhood sanctuary outside Dawnstar.
- Choose to either kill or release Cicero.
- Return to Astrid.
After completing Breaching Security, Gabriella will inform you that there was a “incident” with Cicero and direct you to discuss it with Astrid.
Astrid reveals that Cicero attempted to murder her and the other members of the Dark Brotherhood, grievously wounding Veezara in the process. Arnbjorn pursued him as he fled from the sanctuary. She asks you to search Cicero’s room for clues as to his whereabouts. Inside the room you find five journals, and the final journal indicates that Cicero might be headed for the long abandoned sanctuary outside Dawnstar.
Astrid will grant you use of her horse, Shadowmere. Immediately outside the Sanctuary he will rise from the black, bubbling water. Mount him, and ride to Dawnstar’s abandoned Brotherhood sanctuary.
You will find an injured Arnbjorn outside the sanctuary. He reveals that he and Cicero seriously wounded each other before Cicero escaped into the safety of the sanctuary and instructs you to, “just follow the blood.”
Once inside, Cicero will begin to speak to you. You can find enchanted clothing similar to what he uses on the table:
- Jester’s Boots
- Jester’s Clothes
- Jester’s Gloves
- Jester’s Hat
At this point, summoning Lucien Lachance will add more to the story. He reveals that Sithis does not want you to kill Cicero.
While the sanctuary is abandoned, it is not unoccupied. It is inhabited by ghosts of the previous Dark Brotherhood residents, who will attack on sight.
As you cross the bridge and descend down the stairs you will find two skill books – Fire and Darkness and The Marksmanship Lesson. You can also find unenchanted, lesser quality versions of the Shrouded Armor on the shelf nearby, if you want to keep the appearance of your armor but your own enchantments.
Continuing along, you will enter the cave of the Udefrykte. It is easy to simply sneak past it if you wish. You will also encounter more ghosts as you continue.
At the end, you will find Cicero curled up in a fetal position pretending to be injured. Cicero cautions you that the Night Mother will not be happy if you kill him. At this point it is your choice whether to kill him or not. If you attack him he leaps to his feet, obviously unhurt and gleefully screams, “Haha! Behold the final trick of the Fool of Hearts! You think me near death? Haha! Think again.”
His corpse, if you choose to kill him, contains:
- Cicero’s Boots
- Cicero’s Clothes
- Cicero’s Gloves
- Cicero’s Hat
- A leveled, unenchanted dagger
These items have a combined value of 4644 gold if you wish to sell them. If you decide not to kill him he returns to serve after you complete Hail Sithis!. He can also potentially be a follower. Note that you can pickpocket those items (perks needed) except for the body armor.
Regardless of your decision, the quest is now complete. Speak to Astrid to begin your next mission.