You’re wandering through the freezing slush of Windhelm, maybe looking for a merchant or just trying to stay warm, when you overhear a whisper about a kid. Aventus Aretino. He’s performing a ritual. He’s trying to summon a group of professional killers to take out a cruel orphanage headmistress. Honestly, it’s one of the most iconic moments in RPG history because it’s so grounded and gritty compared to fighting world-eating dragons. But starting the dark brotherhood quest skyrim players love so much isn't just about murder; it's about a slow descent into a family of outcasts that eventually breaks your heart.
The first time you step into that Shack after being kidnapped by Astrid, the game changes. It’s no longer about being the heroic Dragonborn. You’re a cold-blooded tool. Or are you?
How to Actually Start the Dark Brotherhood Quest Skyrim Players Often Miss
Most people think you just talk to Aventus and you're in. That’s only half the battle. You have to kill Grelod the Kind—who, let’s be real, totally deserves it—and then you have to go to sleep. In a bed. In the game. This is where a lot of new players get stuck. They finish the "Innocence Lost" quest and then spend ten hours clearing bandit camps wondering why the assassins haven't called. You need to trigger that courier delivery. The note that just says "We Know" with the black handprint is arguably the best piece of physical lore in the Elder Scrolls V.
Once you wake up in the Abandoned Shack, Astrid gives you a choice. Three captives. One contract. You can kill one, two, or all three. Or, if you’re feeling particularly righteous, you can actually kill Astrid herself. Doing that completely shuts down the questline and starts "Destroy the Dark Brotherhood!" instead. It’s a shorter, much less rewarding path, but it’s there for the paladin types who can't stomach the wetwork.
But if you stay? You get the gear. The Shrouded Armor is statistically some of the best early-game light armor you can find, specifically because of the muffled movement and double sneak attack damage on the gloves.
The Night Mother and the Internal Schism
The middle of the dark brotherhood quest skyrim arc is where the writing really shines. You aren't just a mindless drone. You’re caught between the old ways and the new ways. Astrid represents the "modern" Brotherhood—they’re basically a gang of mercenaries who happen to wear leather. They don’t care about the Five Tenets. They don’t care about Sithis. They just want to get paid and survive.
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Then Cicero shows up.
Cicero is polarizing. Some players find his voice acting—done by the brilliant Andy Morris—absolutely grating. Others see him as the only true believer left. When he brings the Night Mother’s coffin to the Falkreath Sanctuary, he brings the "old religion" back with him. This creates a massive rift. Astrid is jealous. She’s threatened. She’s the leader, but the Night Mother (the literal unholy matron of the guild) chooses you as the Listener. Not her.
Why "Whispers in the Dark" is the Turning Point
This specific mission is claustrophobic. You’re forced to hide inside the Night Mother’s coffin. It’s gross. It’s silent. And then she speaks. If you’ve been playing Skyrim as a power fantasy, this is the moment the game reminds you that you’re a servant to something much darker and more ancient than a simple guild leader. The tension between the family members—like the vampire child Babette or the grumpy mage Festus Krex—starts to boil over here. It’s masterful pacing. It makes the eventual betrayal feel like a physical punch to the gut rather than just a scripted plot point.
Death Incarnate: The Fall of the Sanctuary
Eventually, the questline leads you to the biggest contract in the history of the franchise: killing the Emperor of Tamriel, Titus Mede II. But before you get to the high-stakes political assassination, everything falls apart.
Astrid betrays you.
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She sells you out to the Penitus Oculatus to save her "family," but in doing so, she ensures their destruction. The mission "Death Incarnate" is chaotic. The Falkreath Sanctuary is on fire. Your friends—characters you’ve spent dozens of hours with—are being slaughtered. Seeing Festus Krex pinned to a tree by a dozen arrows is a sight most players never forget. It’s a brutal reminder that in the world of the dark brotherhood quest skyrim, there are no happy endings. Even the "success" of the quest involves pulling Astrid’s charred body out of a ritual circle so she can ask you to kill her. It’s heavy stuff for a game that usually lets you feel like an invincible god.
Is the Reward Worth the Bloodshed?
Let's talk logistics. If you stick it out and actually assassinate the Emperor on the Katariah, you get 20,000 gold. In 2011, that felt like an infinite amount of money. In the modern Special Edition or Anniversary Edition, with all the player homes and expensive creation club content, it still holds up as the single biggest payout in the game.
But you also get:
- Shadowmere: A horse that is basically a tank and can survive a fall off a mountain.
- The Blade of Woe: One of the highest base-damage daggers in the game, perfect for assassin builds.
- Summon Lucien Lachance: Long-time fans of Oblivion will recognize this spectral assassin. His dialogue is a goldmine of lore references.
- Windshear: If you find this scimitar on the Emperor’s ship, you’ve essentially broken the game. It staggers enemies almost every hit.
The new sanctuary in Dawnstar is a bit lonely, though. Even after you spend the gold to upgrade it and hire new initiates, it never quite feels like the "family" you had in Falkreath. That’s intentional. It’s a bittersweet victory.
Common Misconceptions About the Dark Brotherhood
A lot of people think you have to be a stealth archer to do these quests. You don't. While the bonus objectives usually reward "stealthy" kills, you can absolutely walk into a target's house in full Daedric plate armor, swing a warhammer, and walk out. You might lose a small gold bonus, but the quest moves forward just the same. Bethesda designed these missions with flexibility in mind.
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Another big mistake? Killing Cicero.
Look, he’s annoying. He tried to kill the other members. But if you spare him, he becomes one of the most powerful and unique followers in the entire game. He has unique combat barks, high sneak stats, and he’s one of the few followers who doesn't judge you for committing crimes. Plus, the Night Mother actually wants him alive. Killing him is satisfying in the moment, but you lose out on some of the best late-game companion content.
Actionable Steps for Your Next Playthrough
If you’re planning on diving back into the dark brotherhood quest skyrim line, here is how to maximize the experience:
- Level your Illusion magic first. Being able to cast "Invisibility" or "Fury" makes the bonus objectives (like killing a target in a specific city) incredibly easy and much more satisfying.
- Wait to do the "Bound until Death" quest. This is the wedding assassination. If you wait until you have a high level in Smithing or Enchanting, you can create a specialized "wedding gift" (a poisoned bow or dagger) that makes the kill legendary.
- Read the journals. In the Falkreath Sanctuary, everyone has a diary or a backstory. Reading Arnbjorn’s thoughts on being a werewolf or Gabriella’s notes on her kills adds a layer of E-E-A-T (Experience, Expertise, Authoritativeness, and Trustworthiness) to the world-building that you miss if you just rush the markers.
- Keep the Jester's Clothing. Even if you don't wear it, the enchantments on the clothing you find in the Dawnstar Sanctuary are unique and can't be found anywhere else.
The Dark Brotherhood isn't just a questline. It’s a tragedy wrapped in a stealth game. Whether you’re doing it for the gold, the gear, or just to hear the Night Mother’s creepy whispers, it remains the high-water mark for Bethesda’s quest design. Just remember: stay out of the shadows, and always watch your back. Sithis is always watching.