How to Trigger the Dark Brotherhood Questline
To start your journey with the Dark Brotherhood in Oblivion Remastered, you first need to get your hands dirty—literally. You must kill a non-hostile NPC in cold blood. This act cannot be performed during combat with a marked enemy, so you’ll need to find a civilian or neutral character and take them out quietly. For the safest results, carry out the kill at night, in a secluded area, to avoid any witnesses or bounties.
Once you've committed the murder, your next step is to sleep in any bed. This can be done at an inn, a player home, or a camp—anywhere that allows resting. Upon waking up, a mysterious figure named Lucien Lachance will appear to you, introducing the 'A Knife in the Dark' quest. This moment marks your official invitation into the secretive world of the Dark Brotherhood.
Visiting the Inn of Ill Omen
The first objective after receiving the quest is to head to the Inn of Ill Omen, which is located just southeast of the Imperial City. Fast travel there if possible to save time. Once you arrive, wait until nightfall. This is important because nighttime ensures that the inn’s inhabitants are in their rooms, making your next task much easier.
Inside the inn, look to your left for a trap door that leads to the basement. Navigate your way to the far end where you'll find a room with a sleeping man. This is your target. Make sure you're not seen before attacking—stealth is your best friend here. Take him out silently to complete this part of the initiation.
Resting to Proceed
After the deed is done, look for a nearby bed to rest in again. Resting for even just one hour will be enough. Lucien Lachance will make a second appearance after your rest, congratulating you on completing the task and formally welcoming you to the Dark Brotherhood. At this point, you’ll receive a confirmation and achievement for joining the faction.
Heading to Cheydinhal for Final Initiation
Your next destination is Cheydinhal, where the Dark Brotherhood Sanctuary is hidden. Head to the marked location on your map, which leads to a locked and barricaded door near the eastern part of the city. The door is locked, so ensure your lockpicking skill is decent or that you have enough lockpicks on hand. Again, performing this task at night is advised to avoid unwanted attention.
Once inside, proceed to the room on the right, which leads down to the abandoned basement. Follow the corridor until you reach a mysterious door that prompts a password check.
Answering the Secret Question
At the final door, you’ll be asked a riddle: "What is the color of night?"
Respond with: "Sanguine, my brother."
Answering correctly grants you entry into the Dark Brotherhood Sanctuary, where you’ll meet Ocheeva, your main contact and the next step in the questline. After your dialogue with her, the follow-up quest "Welcome to the Family" will begin, officially starting your journey with this sinister guild.
Key Takeaways
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Kill a civilian to trigger the quest.
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Sleep to summon Lucien Lachance.
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Visit the Inn of Ill Omen and eliminate your target.
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Rest again to continue the quest.
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Travel to Cheydinhal and enter the Dark Brotherhood Sanctuary.
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Use the password “Sanguine, my brother” at the door.
Wrapping Up the 'A Knife in the Dark' Quest
Joining the Dark Brotherhood in Oblivion Remastered is one of the most rewarding experiences in the game, especially for players who enjoy stealth and morally ambiguous roleplaying. By completing 'A Knife in the Dark', you've opened the door to an entire questline filled with intrigue, betrayal, and secret assassinations.
From murdering your first unsuspecting NPC to whispering the coded phrase at a hidden sanctuary door, each step builds suspense and sets the tone for the missions ahead. You’ve now gained access to the Brotherhood's hidden base and new contracts, gear, and storyline content—setting you up for hours of dark adventure.
Whether you’re in it for the rewards or the thrill of living in the shadows, the Dark Brotherhood welcomes those willing to make the ultimate choice.
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