You don’t find the Dark Brotherhood. They find you, usually while you are asleep, and you wake up in a shack with three hooded strangers and an assassin sitting on a cabinet. Then Skyrim asks a question most players answer in about four seconds: join them, or end them?
Let me break this down for you: how the questline starts, what the choice in the shack really locks in, every quest on the join path, and what each side pays out. All of it works the same in the Special Edition and Anniversary Edition.
How to Start the Dark Brotherhood Questline
Everything begins with Innocence Lost. A boy named Aventus Aretino in Windhelm is performing the Black Sacrament to summon an assassin, and his target is Grelod the Kind, the anything but kind matron of Honorhall Orphanage in Riften.
- Ways in: hear the rumor about Aventus in Windhelm, talk to him directly at his family’s house, or ask the Honorhall orphans about him.
- The job: kill Grelod, then tell Aventus it is done.
- The follow up: some time later, when you sleep, you wake up in an abandoned shack. That starts With Friends Like These…
The Shack: Join or Destroy
Astrid, leader of the Falkreath Sanctuary, explains that you stole the Brotherhood’s contract on Grelod. To repay the debt, one of the three hooded captives has a contract on their head, and you have to pick who dies.
- Join: kill any one of the three hostages (or all of them; it makes no difference). Astrid gives you the way to the Sanctuary and the questline continues.
- Destroy: attack Astrid instead. With Friends Like These… fails and Destroy the Dark Brotherhood! begins.
Hot Take: this is a one time decision. The shack is your only chance to turn on the Brotherhood, and once you go down the destroy path, you can never join. Make a manual save before you open your eyes in that shack, because you’d be surprised how many people get this wrong with one stray swing.
The Join Path: Every Quest in Order
| # | Quest | What happens |
|---|---|---|
| 1 | Innocence Lost | Kill Grelod the Kind for Aventus Aretino |
| 2 | With Friends Like These… | Kill a hostage in the shack |
| 3 | Sanctuary | Enter the Falkreath Sanctuary and take your first contracts |
| 4 | Mourning Never Comes | Help Muiri in Markarth get her revenge |
| 5 | Whispers in the Dark | Keep an eye on Cicero, the Night Mother’s keeper |
| 6 | The Silence Has Been Broken | Meet Amaund Motierre at Volunruud |
| 7 | Bound Until Death | Assassinate Vittoria Vici at her wedding in Solitude |
| 8 | Breaching Security | Kill and frame Gaius Maro, son of Commander Maro |
| 9 | The Cure for Madness | Deal with a traitor inside the Brotherhood |
| 10 | Recipe for Disaster | Take the identity of the Gourmet |
| 11 | To Kill an Empire | Attempt to kill Emperor Titus Mede II at Castle Dour |
| 12 | Death Incarnate | Survive the Penitus Oculatus assault on the Sanctuary |
| 13 | Hail Sithis! | Finish the biggest contract in Brotherhood history |
Delayed Burial, where you help a jester with a broken wagon wheel on the road, is an optional first meeting with Cicero. It does not change the main story much, but it is a nice bit of foreshadowing.
Side Contracts
Between story quests, Nazir at the Sanctuary hands out contracts. Targets include Narfi near Ivarstead, Beitild in Dawnstar, Anoriath in Whiterun, Agnis at Fort Greymoor, Maluril in Mzinchaleft, Helvard in Falkreath and Safia aboard her ship, the Red Wave. Some come with bonus objectives for a specific kill method, which pays extra gold.
Rewards: Join vs Destroy
The Math: joining gets you a full questline, unique gear and a home base. Destroying gets you a short quest and a payout. Spoiler: it’s not even close.
- Shrouded Armor: a light armor set built for assassins, with bonuses that suit sneaky play.
- Blade of Woe: Astrid’s dagger, one of the strongest daggers in the game. On the destroy path you loot it from her body, so both sides can get it.
- Shadowmere: the Brotherhood’s black horse, with a huge health pool that makes it one of the toughest horses in Skyrim.
- Dawnstar Sanctuary: a new base near the end of the questline, with upgrades you can unlock afterward.
- Marked for Death: the Falkreath Sanctuary holds a Word Wall for this shout, reachable on either path.
The destroy path sends you to the Sanctuary anyway, this time to clear it out, and ends with a gold reward from the Penitus Oculatus. Fine for a hero character, but you trade a dozen quests for one.
Lore Drop: the Brotherhood worships Sithis and serves the Night Mother, whose voice speaks only to the Listener. Lore nerds, this one’s for you: her coffin arrives at the Sanctuary with Cicero, and who ends up hearing her voice is the twist of the whole questline.
Actually Do This
- Build for stealth: sneak attacks with daggers make most contracts trivial. Our stealth archer build also works, and the best beginner build covers the basics.
- Grab the Stone of Barenziah: one of the stones sits in the Falkreath Sanctuary; see our Barenziah Stones guide for the rest.
- Do the bonus objectives: they pay more and are usually more fun than a plain stab.
More guides are in the Skyrim hub, and our Skyrim Special Edition player stats show plenty of PC players still waking up in that shack.
Dark Brotherhood FAQ
How do you join the Dark Brotherhood in Skyrim?
Complete Innocence Lost by killing Grelod the Kind, then sleep. You wake up in a shack with Astrid; kill one of the three hostages to join.
Should you join or destroy the Dark Brotherhood?
Join, unless your character would never do it. Joining gives you the full questline, Shadowmere and the Shrouded Armor; destroying gives a short quest and gold.
Which hostage should you kill?
Any of them. Astrid accepts any kill, and killing all three is fine too.
Can you join the Dark Brotherhood after destroying it?
No. Attacking Astrid in the shack locks you out of the join path for good.
Actually Do This: finish Innocence Lost, save before you sleep, pick a hostage, and enjoy one of Skyrim’s best questlines. Hail Sithis.
