The Dark Brotherhood represents one of the most iconic and secretive assassin guilds in The Elder Scrolls V: Skyrim. Joining this notorious faction opens up a compelling storyline filled with high-stakes contracts, unique gear, and memorable companions. Understanding the exact steps required to initiate contact with the guild allows players to seamlessly begin their journey into the shadows.

Initiating the Aretino Residence Quest

To begin your recruitment process, you must first travel to the city of Windhelm and locate the Aretino Residence. Inside, a young boy named Aventus Aretino is attempting to perform the Black Sacrament ritual to summon an assassin. Speaking with Aventus unlocks the quest Innocence Lost, which serves as the entry point into the faction's storyline.

Aventus asks you to eliminate Grelod the Kind, the tyrannical mistress of the Honorhall Orphanage located in Riften. Traveling to Riften and completing this task proves your capability to the young boy. Returning to Aventus concludes the initial favor and sets the stage for the Dark Brotherhood to take notice of your actions.

Receiving the Mysterious Note

After completing the quest in Riften, you must wait for a courier to deliver a mysterious message. Traveling to any major city or waiting for twenty-four in-game hours usually triggers the delivery. The note simply features a black handprint accompanied by the words We Know.

Receiving this note indicates that Astrid, the leader of the Skyrim sanctuary, has acknowledged your intervention. To trigger the next phase, your character needs to sleep in any bed within a tavern or home. Upon waking, you will find yourself relocated to a secluded cabin far from the nearest town.

Confrontation in the Abandoned Shack

Inside the Abandoned Shack, Astrid presents you with a decisive test involving three bound captives. To fulfill her demand, you must execute at least one of the captives to compensate for taking the contract assigned to the Brotherhood. Your choice determines how Astrid responds, though fulfilling the execution earns her approval.

Once you satisfy Astrid's requirement, she provides the passphrase needed to access the primary sanctuary. She directs you toward the hidden entrance located just outside Falkreath. Entering the sanctuary officially welcomes you as a member of the guild, unlocking specialized armor and initial contracts.

Maximizing Rewards and Faction Benefits

Joining the guild yields substantial advantages for stealth-oriented characters, including the powerful Shrouded Armor set. This gear provides substantial bonuses to sneak mechanics, muffles movement noise, and increases physical damage dealt with one-handed weapons. Completing additional contracts given by Nazir further increases your gold earnings early in the storyline.

As you progress through the main questline, you gain access to unique followers and powerful artifacts like the Blade of Woe. Navigating the guild's storyline allows players to experience some of Skyrim's most intricate stealth missions. Adhering to optional objectives during contracts maximizes both financial compensation and exclusive legendary equipment rewards.