You’re sleeping in a crusty bed in some freezing Windhelm inn, and suddenly, you wake up in an abandoned shack. It’s a classic. Honestly, if you haven’t been kidnapped by Astrid after killing Grelod the Kind, have you even played the game? The Skyrim Dark Brotherhood—often just called the assassins guild by players who can't remember the lore names—is easily the most cohesive, dark, and rewarding faction in Bethesda’s 2011 masterpiece. While the Companions are just "go here, hit thing" and the Mages Guild feels like a rushed weekend retreat, the Brotherhood actually makes you feel like a professional killer.
It starts with a rumor. You hear about a kid named Aventus Aretino performing the Black Sacrament. It’s creepy. He’s stabbing a heart with a human bone. Most games would make this a minor side quest, but in Skyrim, this is your ticket into a secret society of shadow-dwelling murderers.
How to Actually Join the Skyrim Dark Brotherhood Without Messing It Up
Most people think you just wait for a letter. That’s wrong. You have to be proactive. First, you go to Windhelm and find the Aretino Residence. Pick the lock. Talk to the kid. He wants a woman named Grelod the Kind dead. She’s the head of the Honorhall Orphanage in Riften, and she is, ironically, a monster.
Go to Riften. Kill her. It doesn't matter how. You can punch her in the face in front of the children, and they’ll literally cheer for you. After that, you just go about your business until a courier hands you a note with a black handprint that says "We Know." Then, find a bed. Sleep for a few hours. When you wake up, you’re in the shack with Astrid. She gives you a choice: kill one of the three captives, or kill her.
Pro tip: Don’t kill her. Unless you want to destroy the faction entirely, which is a much shorter and less interesting questline. Killing one of the captives (it doesn't matter which one, though Vasha is a jerk) gets you an invite to the sanctuary near Falkreath.
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The Real Vibe of the Falkreath Sanctuary
The first time you walk into that sanctuary, it feels like home, but a very murdery version of it. You’ve got Festus Krex, an old wizard who hates everyone. You’ve got Babette, who looks like a child but is actually a three-hundred-year-old vampire. And then there’s Cicero.
Cicero is divisive. Some players find the jester’s voice grating; others think he’s the only one actually loyal to the Night Mother. He arrives later with a giant coffin containing the corpse of the Night Mother herself. This is where the Skyrim Dark Brotherhood shifts from a band of mercenaries to a religious cult. You, the player, eventually become the Listener. This means you’re the only one who can hear the Night Mother’s voice. It’s a big deal. It creates a massive rift between you and Astrid, who prefers running things like a business rather than a religion.
Why the Contracts Feel Different Than Other Quests
In the Thieves Guild, you're stealing stuff. Boring. In the Skyrim Dark Brotherhood, you’re orchestrating high-stakes political assassinations.
Take the "Bound until Death" quest. You have to kill Vittoria Vici, the Emperor’s cousin, at her own wedding in Solitude. This isn't just a "point and click" mission. You can push a gargoyle off a ledge to crush her. You can snipe her from a balcony. You can even use a Frenzy potion to make her new husband do the deed for you. The game rewards creativity here. If you kill her while she’s addressing the crowd, you get a bonus reward: the Ancient Shrouded Armor.
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The Gear is Actually Useful
Most faction armor in Skyrim is kind of mid-tier. The Shrouded Armor is different.
- The boots give you Muffle (completely silent movement).
- The gloves double your sneak attack damage with one-handed weapons.
- The cowl gives you a 20% bow damage boost.
If you’re playing an Assassin/Thief build, you basically never take this stuff off. Even the standard Shrouded Armor you get at level one is better than most heavy plate armor for a stealth build because of the sheer utility.
The Tragedy of the Penitus Oculatus Raid
Things go south. They always do. Eventually, the Emperor’s personal guard, the Penitus Oculatus, finds the sanctuary. This is the emotional peak of the questline. Seeing the sanctuary on fire and finding your "family" members dead—like Veezara or Arnbjorn—actually hurts. Bethesda nailed the pacing here. You go from feeling invincible to being trapped in the Night Mother’s coffin while the world burns around you.
The betrayal by Astrid is a weirdly human moment. she wasn't some mustache-twirling villain; she was just scared of losing control. She sold you out to Commander Maro to save her "family," and it backfired spectacularly. Finding her charred body in the ritual circle is one of the darkest images in the game. She asks you to kill her with the Blade of Woe. It’s grim. It’s perfect.
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The Ultimate Hit: Killing Titus Mede II
The finale of the Skyrim Dark Brotherhood is the most ambitious quest in the base game. You aren't just killing a bandit leader or a dragon; you are literally assassinating the Emperor of Tamriel.
You board the Katariah, his private ship. You fight your way through his elite guard. When you finally reach him, he doesn't fight back. He’s just sitting there, looking out the window. He knows it’s coming. He even asks you to kill the guy who put the hit out on him once you’re done with him. It’s a moment of surprising dignity for a character who has basically no screen time.
The payoff? 20,000 gold. In 2011, that was a fortune. Even in 2026, with all the mods and expansions, that’s a massive chunk of change.
What People Get Wrong About Cicero
There's a huge debate in the community: Do you kill Cicero or let him live?
If you listen to the ghosts (specifically Lucien Lachance, whom you can summon as a spectral assassin), he tells you that the Dread Father doesn't want Cicero dead. Cicero is the only one who followed the Tenets. If you spare him, he eventually becomes a follower. Honestly, he’s one of the best followers in the game because he has unique combat barks and he’s "essential," meaning he can’t be killed by enemies. Plus, his dancing is top-tier entertainment when you’re stuck in a boring cave.
Actionable Tips for Your Next Playthrough
If you’re jumping back into Skyrim and want the most out of the assassins guild, do these things:
- Get the Blade of Woe early. You can actually pickpocket this from Astrid if your skill is high enough, or just wait until the end of the questline to get it naturally. It’s the best dagger for life-leeching.
- Use the Spectral Assassin. Summon Lucien Lachance often. He has unique dialogue for almost every major quest location in the game. He’ll comment on the history of the places you visit.
- Don't rush the wedding. In "Bound until Death," wait for Vittoria Vici to stand on the balcony to address the guests. That’s the "cinematic" way to do it.
- Invest in the Dawnstar Sanctuary. After the main quest ends, you can spend your 20,000 gold to fix up the new base. It adds a torture chamber which, while dark, provides a way to find hidden treasure caches around Skyrim.
- Check the "Hidden" rewards. Talk to every member of the family after every major mission. Gabrielle will give you a token that lets you get your fortune told by Olava the Feeble in Whiterun, which unlocks a side quest for the best armor in the game.
The Skyrim Dark Brotherhood isn't just about the kills; it’s about the shift in your character's identity. You go from being a random prisoner to the most feared person in the province. It’s the one faction where your actions feel like they have genuine, world-altering consequences. You’re changing the political landscape of the Empire, one throat-slit at a time.