The Dark Brotherhood is a guild made up of assassins who are summoned by citizens of Skyrim to carry out assassination contracts. Love stealth and murder? The Dark Brotherhood is the perfect guild to choose as your new Skyrim family.
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Starting the Dark Brotherhood Quest
Kickstarting the Dark Brotherhood quest is simple. First, you must travel to Windhelm, which is located on the northeastern part of the map (southeast of Winterhold). Once there, you’ll need to wander around until you overhear someone talking about Aventus Aretino. This will trigger the miscellaneous quest that you can select to point you to the Aretino residence.
Alternatively, you can head to the Sleeping Giant Inn in Riverwood and ask the innkeeper for gossip. He will tell you about what Aventus has been up to. You can also visit Honorhall Orphanage in Riften, in which you will also hear about Aventus.
Fulfilling Aventus’ Request
Once you’ve heard the rumor about Aventus and highlighted the quest to speak with him, you can follow the arrow on your map to the Aretino residence in Windhelm. Note that you’ll need to have at least one lockpick, as you must pick a novice lock to enter the residence.
Once there, you’ll find Aventus performing the Black Sacrament ritual. He assumes you’re there responding as a Dark Brotherhood member. Aventus then requests that you murder Grelod the Kind, who runs the Honorhall Orphanage in Riften.
Travel to Riften, murder Grelod (note: it doesn’t matter if people witness you do this), and wait 24 hours. After this, a courier will come find you. The courier will deliver a mysterious note that reads, “We know.”
Once you’ve received the note, simply go to sleep for any amount of time. When you wake up, you will have been abducted by a member of the Dark Brotherhood. You will speak with Astrid, thus kickstarting the initiation into the guild.
Passing Astrid’s “Test”
According to Astrid, you owe the Dark Brotherhood a murder. You stole a murder from the guild by letting Aventus think you were a member and then killing Grelod. Therefore, Astrid instructs you to turn around and kill one of three captives in the room.
You’re told to kill whichever one you think has a contract out for them. Essentially, you must figure out and murder which person angered someone enough to want them dead.
Fortunately, there is no wrong answer here. You can kill any one of the three (or all of them), and Astrid will still invite you to join the Dark Brotherhood. After her “test,” simply follow Astrid’s instructions, and you’re well on your way to being the most dangerous assassin in Skyrim.