Joining the Dark Brotherhood in Skyrim is actually fairly easy to accomplish once the player knows how to get started. With the Sithis-worshipping cult being a fan favorite in the Elder Scrolls series, new players will naturally want to find a way to join the murderous group as soon as possible. But murdering a civilian or three will not be enough to get their attention. Instead, the player will have to murder a very specific civilian who is located in one of Skyrim’s various holds.
The Dark Brotherhood offers the Dragonborn a variety of rewards for joining their guild, but chief among them include the ability to make a lot of gold by being an assassin. Continue advancing in the guild’s questline and eventually the player will gain access to new weapons, armor, followers, and a whole lot more to go with an assassin character build.
Finding a possible lead to the Dark Brotherhood is possible even in the early game of Skyrim. Just head to the nearest inn and ask about any rumors they may have heard. The innkeeper will eventually make mention of a child named Aventus Aretino who is allegedly trying to make contact with the sinister guild. This lead will direct the player to the city of Windhelm in Eastmarch, and the rumor’s validity quickly gets reinforced when even the locals mention how the "Aretino boy” is on a dark path.
How to Join the Dark Brotherhood in Skyrim
Head towards the western portion of Windhelm in Skyrim and locate the Aretino residence, which is located just behind a triggered event where a child and a Dunmer are discussing the rumors. Pick the novice lock on the front door and head inside. Almost immediately upon entering the player should hear a child muttering some odd chants, and the house itself is mostly bereft of furniture. Indeed, the house’s most defining feature is the ritual area Aventus has set up, with the boy chanting about a "sweet mother" in front of human remains.
The boy is performing the infamous Black Sacrament, and upon seeing the player, will immediately assume the Dragonborn is the promised Dark Brotherhood emissary he was trying to summon. Regardless of how the player responds, Aventus will immediately tell the Dragonborn his backstory and reveal that he wants the player to kill a woman called Grelod the Kind.
Speaking to Aventus automatically triggers the “Innocence Lost” quest, and it can be completed once the Dragonborn completes the contract that was thrust upon them. Grelod the Kind is located in Riften and resides within Skyrim's Honorhall Orphanage. This orphanage has little to no security and naturally Grelod herself is a frail woman. Trying to complete a stealthy kill can be complicated due to the sheer amount people inside the orphanage itself, but overall it's not a difficult task.
Killing Grelod is the only objective, there is no need to get away with it or to make the murder seem like an accident. Furthermore, while this is not evident to the player at first, no one inside the orphanage itself (aside from Constance) will take offense to Grelod’s sudden demise. The Dragonborn can quite comically walk inside the orphanage during the day, approach Grelod in front of her kids, and kill her right then and there with no consequences. The kids are cheering, Constance is seemingly incapable of informing the guards, and no one outside notices anything amiss.
With Grelod dead just head back to Windhelm and inform Aretino of the murder. He will be ecstatic and give the player a reward in the form of a unique heirloom valued at 100 gold. A paltry reward on its own, but the murder of an old woman in her own orphanage is news that is bound to spread.
With the Skyrim quest completed, all the player needs to do to meet a Dark Brotherhood agent is to go to sleep. The Dragonborn will be abducted in the night and taken to an abandoned shack, the quest “With Friends Like These...” appearing in the journal. A woman named Astrid will converse with the player and task them with killing one of the other people inside the shack as repayment for “stealing” a Dark Brotherhood contract. Kill one (or multiple) of the bound people inside the shack and talk to Astrid again.
Pleased with the Dragonborn’s choice, she will extend the player an invitation to join the Dark Brotherhood in Skyrim and give them the passphrase for their sanctuary in Falkreath. The black door to this sanctuary is located just outside the city of Falkreath and close to the Roadside Ruins. Approach it, give it the correct passphrase, and enter the Dark Brotherhood Sanctuary. By talking to the waiting Astrid again, the quest will be complete and the player will officially be considered part of the guild.
The Elder Scrolls V: Skyrim Anniversary Edition is available on Xbox One, Xbox Series X|S, PlayStation 4, PlayStation 5, and PC