Joining the Dark Brotherhood in The Elder Scrolls 4: Oblivion Remastered unlocks a unique set of quests with valuable rewards, assuming you meet the Brotherhood’s special requirements. Dark Brotherhood quests have bonus objectives to complete, so whether you accomplish your skullduggery with elegance determines what you get in the end.
This guide explains how to join the Dark Brotherhood in Oblivion Remastered and which target is the safest one to kill to get started.
How to join the Dark Brotherhood in Oblivion Remastered
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The only way to join the Dark Brotherhood is to kill an innocent person. Sleep in a safe place afterward — any inn or bed in a place where people aren’t trying to kill you will do — and you’ll wake up to see Lucien Lachance watching you. He’ll congratulate you for being a ruthless killer and offer to let you join the Dark Brotherhood if you can prove yourself to him.

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Lucien wants you to kill Rufio for the quest “A Knife in the Dark.” He doesn’t say why, but he tells you where to find him — the Inn of Ill Omen. It’s on the road south of the Imperial City.
Travel there, and you can chat with the proprietor to find out where Rufio is if you want. He’s in the “private quarters,” which is the basement. Enter the cellar hatch by the front door, and go to the room at the hallway’s far end. Rufio is asleep in the bed. You can kill him there, pickpocket him first, or wake him up to hear a little of his story. He admits to murdering a woman and then tries to flee.

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He won’t leave the basement, so there’s no chance of him escaping and you failing the quest. Once he’s dead, sleep in one of the beds to make Lucien appear again.

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After reaffirming your desire to join the Dark Brotherhood, Lucien directs you to a house in Cheydinhal. Enter the basement there, and speak the password: “Sanguine, My Brother.” The branch leader, Ocheeva, will have a chat, and you’ll officially join the Dark Brotherhood. Ocheeva will give you your first quest after that.
Who to kill to join the Dark Brotherhood in Oblivion Remastered

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The target has to be an innocent person. That means it can’t be a bandit or other villain, and it can’t be someone with a legitimate grievance against you — someone you attacked or stole from, for example. Oblivion Remastered marks NPCs who give quests or have some importance to the story or other side quests with a crown icon when you approach them. Don’t kill these people, as you might need them later.

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One popular choice is the Adoring Fan follower, since he rises from the dead a few days after shuffling off the mortal coil. However, he won’t start following you until after you rise through the Arena’s ranks, which can take a little while. It’s a solid way to earn money and progress another faction’s quest, but if you just want to start the Dark Brotherhood quest early, there’s a better way.
It also involves the Arena. Travel there, and enter the spectator area that’s reserved for betting patrons. Kill one of the viewers. There are no guards around, and the other spectators are more interested in watching the murder they have money on than dealing with the murder happening literally right next to them. You can get it done and leave without any pushback, and guards won’t follow you afterward either.