The Elder Scrolls V: Skyrim Dark Brotherhood Quest Guide

The Elder Scrolls V: Skyrim is not a seasonal game. The latest major update is the "Skyrim Anniversary Edition", which includes numerous Creation Club content. On December 5, 2023, an update was released that included Steam Deck compatibility, ultrawide monitor support, and the implementation of the Creations platform. This article is based on information from these versions.

Those who lurk in the shadows of Skyrim, moving history with whispers and blades, are the "Dark Brotherhood." This article provides a comprehensive guide to the entire questline of this fascinating and dangerous assassin's guild. From the Black Sacrament chanted by a boy in Windhelm to the grand scheme of assassinating the Emperor, we will thoroughly explain the steps, choices, and how to obtain legendary rewards such as "Shadowmere" and the "Blade of Woe," perfectly supporting your career as an assassin.

How to Join the Dark Brotherhood and Your First Contract

The path to the Dark Brotherhood begins with a plea for help from a boy named Aventus Aretino, who lives in Windhelm. The "Black Sacrament" he performs will lead your destiny down the path of an assassin.

Step 1: Quest "Innocence Lost"

This is the starting quest. You cannot contact the Dark Brotherhood without completing it.

1. Unlock and enter "Aventus Aretino's House" in Windhelm. Hearing rumors from townspeople will display a quest marker.
2. Talk to Aventus, who is performing a ritual inside, and he will ask you to kill "Grelod the Kind," the matron of the "Honorhall Orphanage" in Riften.
3. Head to Honorhall Orphanage and kill Grelod. It's fine to do it in front of the children, but be careful not to be seen by guards.
4. Return to Windhelm and report to Aventus to receive the "Aretino Family Heirloom" as a reward.

Step 2: Quest "With Friends Like These..."

After Grelod's assassination, the Dark Brotherhood will contact you. Your choice here will significantly influence the rest of the story.

1. After completing "Innocence Lost," sleep for a few hours in any location (in a city or inn is fine).
2. Upon waking, a courier will appear and hand you a "Strange Note" with a black handprint, stating "We Know."
3. After receiving this note, sleep in any bed again, and you will wake up in an unfamiliar "Abandoned Shack."
4. In front of you will be Astrid, the leader of the Dark Brotherhood, and three hooded captives. Astrid will order you to kill one of the three.
5. Once you kill one person as instructed, Astrid will recruit you into the Dark Brotherhood, telling you the location of the "Dark Brotherhood Sanctuary" in the Falkreath region and the passphrase to open the door: "Silence, my brother."
6. Speak the passphrase to the Sanctuary's "Black Door" and enter. Reunited with Astrid, you will officially become a member of the Dark Brotherhood and receive a full set of "Shrouded Armor."

• Note: During the test in the Abandoned Shack, the quest will proceed regardless of which of the three captives you kill. Astrid's purpose is to ascertain whether the Dragonborn hesitates to commit murder. Killing all of them is also acceptable.

Main Quest Walkthrough and Grand Rewards

Once you join the Dark Brotherhood, the main story quests assigned by Astrid, the leader, and side assassination contracts from Nazir will progress in parallel. By advancing the main story, you can obtain unique rewards not available elsewhere.

The Night Mother and the "Listener"

The story takes a significant turn in the quest "Whispers in the Dark." The jester Cicero brings the "Night Mother's" coffin to the Sanctuary, and you are ordered by Astrid to hide inside it. The Night Mother herself then speaks directly to you, naming you the "Listener," a position that has long been vacant. This grants you a special status within the guild, but it creates friction with Astrid, who disregards tradition. The ability to receive an endless supply of assassination quests, "The Dark Brotherhood Forever," from the Night Mother after completing the questline is due to the power of the Listener.

Obtaining the Immortal Horse "Shadowmere"

In the quest "The Cure for Madness," you pursue the deranged Cicero. You corner him deep within the Dawnstar Sanctuary, where he has fled. Upon completing this quest, Astrid will reward you with the legendary black horse, "Shadowmere." Shadowmere boasts very high health and astonishing health regeneration speed, making her a reliable companion who will fight alongside the Dragonborn in combat.

• Choice: Cicero's Fate
  At the end of the quest, you are forced to decide Cicero's fate.
  • If you spare him: You let Cicero go and falsely report to Astrid that you killed him. After the questline is complete, he will return to the Dawnstar Sanctuary and can be taken as a Follower. He is a powerful companion with unique mannerisms.
  • If you kill him: You kill Cicero. You can strip a full set of "Cicero's Gear," light armor with high stealth effects, from his corpse. However, this armor can be obtained later even if you spare him, so if you want a Follower, it is recommended to spare him.

High Value Rewards and Legendary Daggers

In the quests towards the end of the story, you will acquire immense wealth and powerful weapons.

• To Kill an Empire: The climax of the grand plan to assassinate the false Emperor. If you succeed, you will receive a large sum of 20,000 Gold as a reward.
• Death Incarnate: The Falkreath Sanctuary is destroyed by an attack from the Imperial Penitus Oculatus. Astrid, performing the Black Sacrament amidst the flames, entrusts you with "Blade of Woe," a unique dagger enchanted with powerful health absorption, and you witness her final moments.
• Hail Sithis!: The final quest of the Dark Brotherhood. You assassinate the true Emperor, Titus Mede II, on his ship, "The Katariah." After completion, you become the new leader of the Dark Brotherhood. Don't forget to explore the ship, as the unique sword "Windshear" can also be found there.

Renovating the New Base: "Dawnstar Sanctuary"

After the Falkreath Sanctuary is destroyed, the "Dawnstar Sanctuary" becomes your new base in the late stages of the story. After completing the questline, you can ask Delvin Mallory, located in the Ragged Flagon in Riften, to upgrade this Sanctuary. This is done through the quest "Where You Hang Your Enemy's Head...", requiring a total of 19,000 Gold.

• New Banners (1,000G): Refresh the Sanctuary's appearance.
• Master Bedroom (3,000G): A luxurious private room befitting a leader.
• Secret Entrance (5,000G): A hidden passage leading just outside the town of Dawnstar.
• Poisoner's Corner (5,000G): Equipped with alchemy apparatus and rare alchemy ingredients.
• Torture Chamber (5,000G): Four victims are imprisoned here. By torturing them, you can learn the locations of hidden treasures across Skyrim, initiating minor treasure quests.

Another Option: "Destroy the Dark Brotherhood!"

If you do not wish to walk the path of an assassin, you have the option to destroy the Dark Brotherhood. In the quest "With Friends Like These...", if you do not follow Astrid's orders in the Abandoned Shack and instead kill her, the quest "Destroy the Dark Brotherhood!" will begin. Afterward, you will report to Commander Maro in Dragon Bridge and proceed to eliminate all Dark Brotherhood members in the Falkreath Sanctuary. The reward is 3,000 Gold, but you will not obtain any unique rewards such as Shadowmere or the Blade of Woe, so choose carefully.

Conclusion

The Dark Brotherhood questline in The Elder Scrolls V: Skyrim is not merely an assassin's trade, but an epic tale of betrayal, revenge, and rebirth. As the "Listener," the Dragonborn plays a crucial role within the organization, subtly influencing the history of Skyrim. Attractive rewards such as the immortal horse "Shadowmere," the powerful dagger "Blade of Woe," and a large sum of 20,000 Gold are well worth the dangerous missions. The Dragonborn's choices, such as Cicero's fate and the reconstruction of the Sanctuary, shape the finer details of the story. So, will you utter the passphrase to the Black Door and embark on the path of an assassin embraced by Sithis? Or will you eradicate this organization from Skyrim with a blade of justice? The choice is yours.