How to start: Kill Grelod the Kind at Honorhall Orphanage in Riften, then sleep.
Ends with: The Blade of Woe, Shadowmere, the Shrouded Armor and the title of Listener.
The oldest guild of assassins in Tamriel, sworn to the Night Mother and the Dread Father Sithis. This questline is dark, funny, and utterly iconic.
Questline
- 1
Innocence Lost → With Friends Like These…
After killing Grelod, you're abducted by Astrid. Kill one of three captives to pay your "debt" and join the Falkreath Sanctuary.
- 2
Sanctuary Contracts
Complete contracts and quests like Bound Until Death (assassinate Vittoria Vici at her wedding) and befriend the Night Mother, who names you Listener.
- 3
The Emperor Plot
Through The Cure for Madness and Recipe for Disaster, you prepare to kill Emperor Titus Mede II. In To Kill an Empire you slay his decoy at a feast.
- 4
Death Incarnate
The Penitus Oculatus raid and burn the Sanctuary. Astrid, mortally wounded, reveals she betrayed you — and asks you to end her with the Blade of Woe.
- 5
Hail Sithis!
Board the imperial ship The Katariah and assassinate the real Emperor. Rebuild the Brotherhood at the Dawnstar Sanctuary as its Listener.
Instead of joining, you can destroy the Brotherhood in the short quest "Destroy the Dark Brotherhood!" by killing Astrid in the shack instead of a captive and reporting it to a guard — but you'll miss all the rewards above.
The Keeper's Wagon
Somewhere between the early contracts you'll meet Cicero on the road north of Whiterun, his wagon broken down with what he swears is his mother's body inside — really the Night Mother's casket. In "Whispers in the Dark" you spy on him from inside that very coffin once it reaches the Falkreath Sanctuary, and the Night Mother names you Listener and sends you after "The Silence Has Been Broken" — a trip to the Nordic ruin of Volunruud to meet the plot's architect, Amaund Motierre. In "With Friends Like These…", the three bound captives you choose between are a boastful Khajiit named Vasha, a hardened mother of six called Alea Quintus, and a sellsword, Fultheim the Fearless.