How to Join the Dark Brotherhood in Skyrim: Finish 2 Quests

If you have ever wandered through Skyrim and thought, “You know what this dragon-filled civil-war-torn province needs? More morally questionable career options,” then welcome. The Dark Brotherhood is one of the most memorable faction questlines in The Elder Scrolls V: Skyrim, and joining it is surprisingly simple once you know the exact path. The catch is that many players overcomplicate it, miss a trigger, or spend way too long sleeping in random beds like a confused assassin-in-training.

The good news is that learning how to join the Dark Brotherhood in Skyrim really comes down to finishing two quests: Innocence Lost and With Friends Like These… That is the real backbone of the process. Yes, you may hear rumors, find notes, or get sidetracked by a giant trying to launch you into low orbit, but the actual route is much cleaner than it seems.

This guide breaks down exactly how to start the Dark Brotherhood questline, where to go, what choices matter, what rewards you can expect, and what mistakes can slow you down. If your goal is to become Skyrim’s most efficient problem solver with a dagger, black robes, and a suspiciously calm attitude toward murder contracts, you are in the right place.

The Short Answer: How to Join the Dark Brotherhood in Skyrim

If you want the fastest possible answer, here it is:

1. Start the quest Innocence Lost by finding Aventus Aretino in Windhelm.
2. Kill Grelod the Kind at Honorhall Orphanage in Riften.
3. Return to Aventus and finish Innocence Lost.
4. Sleep in a bed after that to trigger With Friends Like These…
5. Meet Astrid in the Abandoned Shack and complete her test.
6. Go to the Dark Brotherhood Sanctuary near Falkreath and enter the faction.

That is it. Two quests. A creepy kid. One extremely unpopular orphanage headmistress. One kidnapping. Very normal Skyrim afternoon.

Quest 1: How to Start and Finish Innocence Lost

Step 1: Find Aventus Aretino in Windhelm

The first step in joining the Dark Brotherhood is triggering Innocence Lost. The most direct way is to travel to Windhelm and locate the Aretino Residence. Aventus Aretino is the boy you need to speak with. You can also hear rumors about him from innkeepers or from people discussing the strange child trying to contact assassins, but going straight to Windhelm is faster and cleaner for players who do not feel like collecting gossip like a medieval podcast host.

When you enter the house, you will find Aventus performing the Black Sacrament, a ritual meant to summon the Dark Brotherhood. He assumes you are the assassin he called for and asks you to kill Grelod the Kind, the cruel headmistress at Honorhall Orphanage in Riften.

Step 2: Travel to Riften and Kill Grelod the Kind

Now comes the key moment. If you want to know how to join the Dark Brotherhood in Skyrim, this is the action that gets their attention. Head to Honorhall Orphanage in Riften and eliminate Grelod.

There is not much tactical challenge here. Grelod is not exactly a boss fight. She is weak, unarmored, and about as intimidating in combat as a wet cabbage. The only real concern is avoiding extra trouble. In most playthroughs, killing her inside the orphanage is the easiest option because the children do not report you, and the scene moves forward quickly.

If you are playing a stealthy character, you can wait until she is isolated and take her out quietly. If you are playing a barbarian with all the subtlety of a falling wardrobe, that can work too. Skyrim is flexible like that.

Step 3: Return to Aventus for Your Reward

After Grelod is dead, go back to Windhelm and speak with Aventus again. This completes Innocence Lost and earns you the Aretino Family Heirloom. More importantly, it sets up the next step in the Dark Brotherhood recruitment chain.

Some players think this is where the faction invite should happen immediately, but Skyrim likes drama. The Brotherhood does not just send a polite welcome letter with a wax seal and a coupon for your first assassination. Instead, you need one more trigger.

Quest 2: How to Trigger and Finish With Friends Like These…

Step 1: Wait for the “We Know” Note

Once Innocence Lost is complete, you will usually receive a Mysterious Note from a courier. It famously says “We Know” and includes the Dark Brotherhood handprint. This is Skyrim’s way of saying, “Congratulations, your extracurricular activities have been noticed.”

Do not panic if the note does not appear instantly. Sometimes the courier takes a little time to catch up. Skyrim couriers are heroic, but they also seem to have a side hustle involving dramatic timing.

Step 2: Sleep in a Bed

After finishing Innocence Lost, sleep in a bed. This is the trigger that launches the second required quest: With Friends Like These… When you wake up, you will not be where you fell asleep. Instead, you will find yourself in the Abandoned Shack, where Astrid waits to test you.

This is the moment many players remember most clearly because it is peak Dark Brotherhood energy: creepy, theatrical, and wildly inappropriate by normal human standards.

Step 3: Speak with Astrid and Make Your Choice

Astrid explains that since Aventus performed the Black Sacrament, the contract technically belonged to the Dark Brotherhood. By killing Grelod yourself, you stole one of their jobs. To settle the debt, Astrid tells you to kill one of three captives in the shack.

Here is the important thing: if your goal is to join the Dark Brotherhood, you need to cooperate with Astrid and complete her little audition. You can kill one captive, two captives, or all three. Once Astrid is satisfied, she will tell you where the sanctuary is and how to enter it.

There is an alternate option, though. You can kill Astrid instead and start the Destroy the Dark Brotherhood! questline. That is a valid roleplaying path, but it is obviously the exact opposite of joining. So if you are here for the assassin lifestyle, do not stab your future boss in the face. At least not yet.

Step 4: Enter the Dark Brotherhood Sanctuary

After the shack scene, travel to the Dark Brotherhood Sanctuary near Falkreath. Speak to the Black Door, answer its question correctly, and enter.

The passphrase exchange is classic Skyrim weirdness:

• Door: “What is the music of life?”
• Answer: “Silence, my brother.”

Once inside, talk to Astrid and you are officially in. Congratulations. You are now a professional assassin with coworkers who somehow feel both deeply unstable and weirdly supportive.

Why Players Think Joining the Dark Brotherhood Is Harder Than It Is

The process is easy once you know it, but a few things confuse people:

The Rumor Step Feels Mandatory

Many guides mention hearing rumors at inns before going to Windhelm. That can help point you in the right direction, but it is not the only route. If you already know where Aventus is, you can save time and go straight there.

The Courier Note Can Be Delayed

Players often assume something broke if the “We Know” note does not show up immediately. Usually, it is just a timing issue. Keep playing, rest later, and the sequence should continue. Skyrim sometimes treats quest progression like a theater production that refuses to start until everyone is standing in the correct spotlight.

The Abandoned Shack Gives You a Morality Curveball

Some players freeze at Astrid’s test because they wonder whether there is a “correct” captive to kill. From a joining perspective, the game does not require you to identify the “right” target. The real choice is whether you will obey Astrid or reject the Brotherhood by killing her.

Best Tips Before You Join the Dark Brotherhood

Use a Stealth Build If You Want the Full Experience

You do not need a stealth character to join, but the Dark Brotherhood questline clearly favors sneaky play. High Sneak, strong daggers, a bow for quiet kills, and illusion spells like Muffle or Invisibility make the whole faction storyline much more satisfying.

Do Not Accidentally Start the Destroy Route

This is the biggest mistake. If you kill Astrid in the shack because you think the game is testing your independence, congratulations, you just locked yourself out of the normal Dark Brotherhood questline. Great roleplay, terrible membership application.

Save Before the Shack Scene

It is always smart to keep a save before With Friends Like These… That way, if you change your mind about joining or want to see both outcomes, you can reload without replaying the whole setup.

What You Get for Joining the Dark Brotherhood

Players do not join the Dark Brotherhood just for the stylish black decor and the unsettling door conversation. The faction offers some of the most entertaining quests in Skyrim, along with useful rewards for assassin-style builds.

Once you are in, you gain access to:

• The full Dark Brotherhood questline
• Shrouded Armor, a great early assassin set
• Unique contracts and gold rewards
• One of the game’s most memorable faction stories
• Later access to iconic items and strong stealth gear

For many fans, this faction remains one of the highlights of Skyrim because the missions feel more personal, theatrical, and creative than a lot of standard dungeon-clearing quests. The Dark Brotherhood does not just ask you to kill targets. It turns murder into performance art, which is not a sentence most fantasy heroes should be proud of, but here we are.

FAQ: How to Join the Dark Brotherhood in Skyrim

Do you really only need to finish two quests?

Yes. To officially join the Dark Brotherhood, the crucial quests are Innocence Lost and With Friends Like These… Everything before or around them is setup, flavor, or optional routing.

Can you join the Dark Brotherhood without killing Grelod?

No, not through the standard path. Grelod’s death is the act that gets the Brotherhood’s attention and moves the recruitment process forward.

Do you have to wait for the “We Know” note?

Usually the note appears, but the bigger trigger is sleeping after Innocence Lost. If the note takes time, sleeping later often advances the process anyway.

Can you spare all three captives in the shack?

Not if you want to join normally. To proceed with Astrid and the Brotherhood, you need to kill at least one captive. Killing Astrid instead starts the anti-Brotherhood route.

Where is the Dark Brotherhood Sanctuary?

It is near Falkreath. Once Astrid gives you the instructions, head there, speak to the Black Door, and answer with “Silence, my brother.”

The Real Appeal of Joining the Dark Brotherhood

Learning how to join the Dark Brotherhood in Skyrim is not just about unlocking another faction. It is about opening one of the game’s most entertaining roleplaying lanes. Maybe your Dragonborn is a silent knife-in-the-dark type. Maybe they are an ex-mercenary who finally found a workplace with dental coverage. Maybe they just like the dramatic aesthetic of whispering passwords at sentient doors.

Whatever your angle, the Dark Brotherhood delivers a questline that feels distinct from the Companions, the College of Winterhold, or the Thieves Guild. It is darker, stranger, and much more willing to look you dead in the eye and ask, “So, how committed are you to this whole murder thing?”

And the answer, apparently, is: committed enough to finish two quests and crawl into a suspicious bed for career advancement.

Player Experience and Practical Tips From Real Playthroughs

One reason this topic stays popular is that the Dark Brotherhood intro creates a genuinely memorable experience. On paper, the steps are simple. In practice, the whole sequence feels like classic Skyrim chaos wrapped in a velvet assassin cloak.

For many players, the journey begins almost by accident. You hear a rumor in an inn, ignore your dragon problem for the hundredth time, and suddenly you are breaking into a house in Windhelm to talk to a child chanting over bones. That is Skyrim in a nutshell: one minute you are saving the world, the next you are taking a freelance homicide request from a deeply committed little weirdo.

The trip to Honorhall Orphanage is often the moment when players realize the game is fully serious about this questline. Grelod the Kind is introduced in a way that makes the moral choice feel less like a gray area and more like the game is handing you a neon sign that says, “Yes, this is the target.” Even players doing good-guy runs often pause, sigh, and say, “Well… technically this might still fit the build.”

Then comes the weirdest part: waiting for contact. Veterans know the courier or sleep trigger is coming, but newer players often think they missed a step. They will fast-travel, clear caves, smith twelve iron daggers, get attacked by wildlife, and only then remember to sleep. Suddenly they wake in the Abandoned Shack, staring at Astrid like they just lost an argument with the universe. It is one of Skyrim’s best “what is happening right now?” moments.

From a gameplay perspective, the experience hits harder if you lean into roleplay. Sneak gear, daggers, illusion magic, and patience make the Dark Brotherhood feel less like a checklist and more like a fantasy assassin simulator. If you barge through every room in heavy armor swinging a warhammer, you can still finish the questline, but the vibe becomes less “legendary killer” and more “angry blacksmith with deadlines.”

Another common player experience is indecision in Astrid’s shack. People overanalyze the captives, trying to decode hidden clues and solve the room like it is a detective quest. That is part of the fun. The game wants you to sit in the discomfort for a second. But if your objective is simply joining the Dark Brotherhood, the truth is straightforward: Astrid wants proof that you will play along. Pick your target, accept the bizarre initiation ritual, and move on.

Players who do join usually remember the sanctuary reveal fondly. The talking door, the shadowy interior, the Shrouded Armor, and the cast of unsettling coworkers all sell the fantasy immediately. It feels like unlocking a secret corner of Skyrim where everyone is equal parts cultist, contract killer, and theater kid.

In the long run, the best experience comes from treating these first two quests as the start of a larger character arc. Whether you are roleplaying a cold professional, a morally flexible thief, or a hero making increasingly terrible life choices, the Dark Brotherhood path gives your playthrough texture. It is not just about joining a faction. It is about the moment your Dragonborn stops asking, “Should I do this?” and starts asking, “Do I look good in black leather?”

Conclusion

If you want to know how to join the Dark Brotherhood in Skyrim, the process is refreshingly direct once you cut through the rumors and confusion. Finish Innocence Lost, then trigger and complete With Friends Like These… Those two quests are the real gateway. Everything else is atmosphere, timing, and Skyrim being delightfully dramatic.

For players who enjoy stealth, dark humor, memorable faction storytelling, and quests that feel a little unhinged in the best possible way, the Dark Brotherhood remains one of the best guilds in the game. It is efficient, stylish, and only slightly horrifying. In Skyrim terms, that counts as excellent workplace culture.