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Skyrim: The Dark Brotherhood Main Questline Walkthrough

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A "gamer" since way before the term was coined, I have been playing video games in one form or another since the 1980s.

Meet the Dark Brotherhood

The Dark Brotherhood is an infamous group of stealthy assassins that spend their lives killing people for great rewards. While the exact going-ons of the group is shrouded in mystery for most citizens of Tamriel, a select few adventurers are hand-picked to join the group.

Many people pray to the Night Mother for assistance in killing particular people, but only a few are employed to carry out the taboo missions.

To become a member of the Dark Brotherhood of Skyrim, you must show a tenacity for killing that many lack and an invitation to this group comes at a more difficult price than in other areas of Tamriel.

The Dark Brotherhood of Skyrim is a great place for Stealth characters to begin their adventures, along with the Thieves Guild which you can do at the same time. The quests within the Dark Brotherhood rely on Sneak and often require you to move around and kill your contracts without being seen.

Leveling your one-handed skill tree is important if you wish to kill your prey with the close-quarters method, but a long-range assassin would do well with Archery. Level these skills until damage multipliers are heightened while in sneak mode.

It isn’t recommended to use spells in these quests, since it is often difficult to cast and land a spell without being seen, forfeiting your secrecy and upping your bounty if you are spotted.

These quests are unlike the Thieves Guild, however, since complete stealth is often unneeded to collect the full bounty from your quest-giver.

Dark Brotherhood Assassin

Dark Brotherhood Assassin

Benefits of Joining the Dark Brotherhood

It is important to note some of the great things that come out of completing the Dark Brotherhood questline:

After beginning the Dark Brotherhood Quest – The Cure for Madness, you receive the demon steed Shadowmere as a permanent horse to ride.

While this Shadowmere is slightly different from previous incarnations, he is basically immortal sans a suicidal jump from a high mountain.

It is rumored that Shadowmere will actually reincarnate approximately 15 days after his death in the area that he met his demise, but it is highly unlikely you will kill him inadvertently in the first place.

He can be used in a number of ways, but his role in skill leveling is one of the most important. He is also much faster than many horses in Skyrim and will often assist you in battles of all kinds, giving you much-needed breathing room for epic battles with nasty enemies. Not to mention he looks really cool.

When you complete the entire questline, you gain the ability to speak with the Night Mother and take quests to kill randomized NPCs. These quests are often easy and wield decent money for the time spent.

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The NPCs that appear in these quests are completely unimportant to the story, so don’t worry about killing any of these characters for fear of messing up future quests. It becomes like clockwork to kill these contracts, and within a short time you can rack up a good amount of gold.

Like many of the other questlines, the Dark Brotherhood gives you a place to hang your hat, even if it is stained with the blood of the innocent. Although you have to spend some money to outfit the area with the various torture chambers and creepy bedroom furniture, it is a great place for beginners to set up house when the more expensive properties are out of reach.

However, the location is slightly poor since Dawnstar is not known for its bustling merchant life.

In the Dawnstar Sanctuary after the Dark Brotherhood Quest – Hail Sithis!, you can recruit initiates to follow you at any point, as well as Cicero if you decline to kill him during the questline.

Initiates are infinite and can be used for whatever purpose you choose, even as a sacrifice in the Daedric Quest – Boethiah’s Calling. While they don’t have many outstanding qualities, they can still be very useful if you aren’t careful in battle and are known for killing your followers.

Delayed Burial (OPTIONAL) Walkthrough

Objectives:

  • Convince Loreius to Fix the Wheel
  • Convince Loreius OR Report Cicero
  • Talk to Cicero OR Talk to Loreius

Before visiting the Aventus Aretino and beginning the questline, travel north of Whiterun on the road. Eventually, you will come across a broken-down cart and you’ll find a weird little guy in a jester’s outfit named Cicero.

Speak with him to find out that the cart is carrying his departed mother (who you will come to know well), and he needs your help to fix the cart and bring her to her new resting place. Tell him you will help and he will recommend you visit Vantus Loreius.

The quest marker will bring you west of Loreius farm, where Vantus Loreius is hanging out with his wife. He seems very hesitant to help since Cicero is such an odd fellow.

You can choose two different routes here: convince Vantus to help, or report Cicero to the authorities. It takes just a few moments to convince Vantus to help, or head over to the road and find a guard.

If you help Cicero by convincing Vantus to help the seemingly innocent man, head back to his cart to find everything fixed.

If you turn in Cicero to the guard, return to Vantus. Both endings give you the same outcome: 50 gold and the murder of the Loreius family by an unknown assailant.

Or so you think….

Delayed Burial Video

Innocence Lost Walkthrough

Objectives:

  • Talk to Aventus Aretino
  • Kill Grelod the Kind
  • Tell Aventus Aretino that Grelod is Dead

To start into the questline for the Dark Brotherhood, there are a number of ways to point you in the right direction.

You can simply visit Windhelm and speak with the nearest guard, who will point you to something odd going on in a house.

You can also ask around in various inns around Skyrim, leading to a miscellaneous quest marker straight to the boy.

Lastly, you can visit the Honorhall Orphanage if you are in the Riften area and talk to any of the young children. Samuel, Hroar, Francois Beaufort, or Runa Fair-Shield will all point you to an escaped orphan who was planning some devious things.

Once you are pointed in the right direction, you have to pick the Novice Lock to get into the creepy house in Windhelm.

Inside, you will find your first connection to the Dark Brotherhood: Aventus Aretino. He is chanting the Black Sacrament, the evil chant to contact the Night Mother and the Dark Brotherhood in order to kill someone.

Even though you “just stumbled upon” him in his home praying to the Night Mother, he believes that you are an assassin sent by the organization to kill his contract, the head of the Orphanage in Riften from where he escaped.

Head to Riften and find this evil woman (with an ironic name), Grelod the Kind cruelly yelling at all her children that they will never leave and must treat her gratefully for all she does for them. After her little banter, stick a weapon in the evil broad’s chest and watch as the children celebrate.

If anyone actually sees you doing this, you will gain a bounty on your head, but if you wait for Grelod to go to bed, a sneak attack will more than suffice.

Head back to Aventus and tell him that you killed the woman and he will give you the Arentino Family Heirloom in gratitude.

When your current quest is done, you will receive a shady message from a courier as soon as you visit another town in Skyrim, or go to sleep to be visited by an ominous assassin.

Thus starts the next quest….

Innocence Lost Video

With Friends Like These… Walkthrough

Objectives:

  • Kill One of the Captives
  • Enter the Dark Brotherhood Sanctuary

Going to sleep after completing the Dark Brotherhood Quest – Innocence Lost will result in awakening in a small shack that you don’t recognize.

Welcome to your first test as an initiate into the deadly world of the Dark Brotherhood.

You don’t have much choice to start, so speak with the masked person sitting on top of some crates. She will introduce herself as Astrid, an initiating member of the Dark Brotherhood.

If you haven’t already noticed the bound and blindfolded people in the center of the room, she will inform you that you must kill one of them to make up for the target you stole from the assassin group.

She explains that one of them has a contract on their heads, and you must find out who it is and kill them to even the score. You can speak to all three and make your best judgment on the matter while completing some Intimidate and Persuasion checks for your speech skill.

(You have an alternate choice here if you don’t want to become a cold-hearted assassin. Instead of choosing to kill one of the targets, turn your weapon on Astrid.

She is a difficult opponent at lower levels, so sneak attacks are wise whenever possible. If you kill Astrid, you can escape from the Abandoned Shack with the key on her corpse, along with the Blade of Woe.

Be forewarned: if you kill Astrid and partake on the next quest, all the future quests with the Dark Brotherhood will be inaccessible from then out. (That means no Shadowmere or future contracts.)

Take your pick of a victim by whatever means you choose. Regardless of your reasoning (or lack thereof), kill your choice and return to Astrid. She will congratulate you on your cold-blooded nature and tell you that it didn’t matter who was the real contract because all of them were innocent.

Instead of leaving you and your unique talents in the crappy shack, she invites you to become a member of the elite organization. Collect the Abandoned Shack Key and learn the phrase to enter the Dark Brotherhood Sanctuary, then leave the other innocent victims behind. Someone will take care of them, or they’ll starve. It hardly matters to a relentless assassin like you now.

Find the Dark Brotherhood Sanctuary with your quest marker and give the newly available option “Silence, my Brother” to the door-keeper. You are greeted by Astrid inside with the Shrouded Armor set, and she tells you that much needs to be done to prepare for the arrival of the Night Mother.

Explore the dank living area of the Dark Brotherhood and visit Nazir to continue your quest.

You are encouraged to equip some, if not all, of the Shrouded Armor for its great enchantments and cool appearance.

With Friends Like These… Video

Sanctuary Walkthrough

Objectives:

  • Speak with Nazir
  • Receive the First Set of Contracts from Nazir

Speak with Nazir in order to begin your test to become an official assassin of the Dark Brotherhood.