So, you’ve decided to end someone’s life in Cyrodiil. Honestly, that’s usually how it starts. You're wandering around some farmhouse or a city street, you commit a cold-blooded murder, and then you go to sleep. Suddenly, a man in a black hood named Lucien Lachance is standing over your bed.
The oblivion dark brotherhood quest isn't just a series of missions. It’s a descent. Most people remember Skyrim's version—the weird kid with the skeleton mom and the kidnapped-in-a-shack intro—but the 2006 Oblivion questline is a completely different beast. It’s darker, weirder, and way more creative with how it lets you be a monster.
How to Get Your Foot in the Door (Without Getting Arrested)
You can't just walk up to a recruiter. Joining the Brotherhood requires you to murder an "innocent." Basically, any NPC that isn't a bandit or a monster. A lot of players go for a beggar or someone isolated like Glarthir in Skingrad after his own quest goes sideways. Once the deed is done, a message pops up: "Your killing has been observed by forces unknown."
Go sleep in a bed. Any bed works. Lucien shows up, gives you a dagger called the Blade of Woe, and tells you to kill an old guy named Rufio at the Inn of Ill Omen. Do that, and you're in.
The Sanctuary is under an abandoned house in Cheydinhal. You’ll need the password—"Sanguine, my brother"—to get through the basement door. Inside, you aren't met with snarling villains. You're met with a family. That’s the genius of the writing. These people are literal serial killers, but they're the only group in the game that actually treats you like a person from day one.
The Quests That Actually Require a Brain
In most RPGs, "assassin" means "go to point B and hit the guy until he dies." Oblivion didn't do that. It gave you "bonuses." If you killed the target in a specific, poetic way, you got better loot.
Take the quest Accidents Happen. You have to kill a guy named Baenlin. You could just stab him. But the bonus? You sneak into his secret crawlspace and loosen the fastenings on a massive mounted head of a Great Hunted Bounder so it falls and crushes him while he’s sitting in his chair. If you pull it off without being seen by his manservant, you get the Sufferthorn dagger.
Then there’s Whodunit?. This is widely considered the best quest in Elder Scrolls history.
- You’re locked in a mansion with five guests.
- They think there’s a treasure hidden inside.
- You have to kill all of them without anyone seeing you do it.
- You can literally talk to them and convince them that someone else is the killer.
You can play the guests against each other until they start murdering themselves. It’s a masterclass in sandbox AI manipulation that modern games still struggle to replicate.
The Turning Point: The Purification
Everything feels great until the mid-game twist. Lucien informs you there’s a traitor in the Sanctuary. His solution? The Purification. You have to kill everyone in the Cheydinhal Sanctuary. Every single person you’ve been chatting with, buying spells from, and calling "brother" or "sister."
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It’s a gut-punch.
You have to kill Ocheeva, the calm leader.
You have to kill Vicente Valtieri, the 200-year-old vampire who was probably the nicest person in the room.
You even have to kill the jerk M'raaj-Dar, who actually apologizes for being mean to you right before the quest starts.
Once they’re dead, you stop taking orders from people. You start taking orders from Dead Drops. You go to a hidden spot (like a hollowed-out tree or a rotten crate), find a letter, kill the target, and pick up your money.
What Really Happened With the Traitor?
This is where the oblivion dark brotherhood quest gets truly messy. As you’re doing these dead drop missions, the targets start feeling... off. You aren't killing nobles or corrupt merchants anymore. You’re killing weirdly specific people, like a whole family or a high-ranking member of the Black Hand.
Lucien eventually hunts you down in a rage. It turns out the "traitor" has been intercepting your orders and replacing them. You’ve been systematically murdering the leadership of the Dark Brotherhood itself.
The ending is grim. You find the real traitor, Mathieu Bellamont, but not before the remaining members of the Black Hand find Lucien. They believe he was the traitor. By the time you arrive at Applewatch, they’ve already tortured and killed him, hanging his body from the rafters.
The Final Showdown at the Night Mother’s Crypt
The questline ends in Bravil, inside the tomb of the Night Mother. Bellamont reveals his motive: the Brotherhood killed his mother when he was a boy, and he’s spent his entire life planning this revenge. It’s a rare moment where the "villain" actually has a point, even if he’s trying to stab you in the face.
Once he's dead, the Night Mother names you the Listener. You’re now the head of the guild.
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The Practical Rewards (Why You Should Care)
The gear you get isn't just flavor; it's some of the best in the game for stealth builds.
- Shadowmere: You get the best horse in the game. She’s fast, she’s essential (meaning she can't die, just gets knocked out), and she’ll actually fight enemies with you.
- The Black Hand Robes: Huge boosts to Sneak, Blade, and Illusion.
- Scales of Pitiless Justice: A quest reward that sits in your inventory and boosts your Strength, Agility, and Intelligence, though it drains your Personality.
- Weekly Income: Once you’re the Listener, you can visit the Lucky Old Lady statue in Bravil once a week to get a "whisper," tell it to the new guy in the Sanctuary, and collect a bag of gold.
Essential Tips for Not Ruining Your Run
If you’re playing this for the first time or jumping back in for a nostalgia trip, keep a few things in mind.
First, don't kill the target's guards unless the quest says it's okay. Killing guards often voids your bonus reward.
Second, use Poisoned Apples. You can buy them from M'raaj-Dar before you have to kill him. If you put one in a target's inventory and remove all other food from their house, they’ll eat it and die instantly. It counts as an "accident" every time.
Lastly, watch your Infamy. Joining the Brotherhood will tank your reputation. If you’re trying to do the Knights of the Nine DLC later, you’ll have to do a massive "Pilgrimage of the Nine Altars" to reset your Infamy to zero before you can wear the Holy Crusader armor.
The oblivion dark brotherhood quest is a reminder of when Bethesda took big risks with their narrative. It starts with a simple murder and ends with you being the lone survivor of a hollowed-out cult, standing in a basement in Cheydinhal wondering if the gold was worth the friends you had to kill.
To make the most of the ending, make sure you head back to the Cheydinhal Sanctuary after becoming Listener. You can recruit a Dark Brotherhood Murderer to follow you around as a permanent companion, which is helpful since most followers in Oblivion are pretty useless.