How To Join The Dark Brotherhood In Oblivion: The Ultimate Guide To Cyrodiil's Infamous Assassins

How To Join The Dark Brotherhood In Oblivion: The Ultimate Guide To Cyrodiil's Infamous Assassins

Ever wondered how to join the Dark Brotherhood in Oblivion? That shadowy guild of professional killers, bound by the will of the Night Mother and the whispers of the Keeper, represents one of the most thrilling and morally complex questlines in The Elder Scrolls IV: Oblivion. Unlike the straightforward Fighter's Guild or Mages Guild, gaining entry requires a specific, often unsettling, set of circumstances. This comprehensive guide will walk you through every clandestine step, from the fateful first murder to becoming a feared Silencer in the sacred halls of the Sanctuary. Whether you're a returning adventurer or a first-time player, understanding the precise triggers and quest flow is essential to unlocking this iconic assassin experience.

The Dark Brotherhood questline is a masterclass in narrative design, offering a dark, character-driven alternative to the main storyline. It’s not just about completing missions; it’s about embracing a new identity, adhering to a strict code, and navigating the intricate politics of a secret society. This guide will demystify the process, providing clear, actionable steps, crucial tips to avoid common pitfalls, and deep insights into what makes this faction so compelling. Prepare to walk the Path of the Night Mother.

The Prerequisite: A Fateful First Kill

Before the Dark Brotherhood ever acknowledges your existence, you must prove your willingness to take a life. This isn't a formal initiation but a necessary precondition that triggers the guild's attention. The game's AI and quest triggers are specific: you must commit a murder that is witnessed by no one and leaves no witnesses. This means no guards, no civilians, and no one who can report the crime. The victim must be a non-essential NPC (not a quest-giver or major character).

Where and How to Make Your First Mark

The most reliable method is to find a secluded spot and an isolated target. Popular early-game locations include:

  • The Great Forest outside the Imperial City: Numerous bandits and wildlife, but be cautious of patrols.
  • Remote farms or ruins across Cyrodiil: Look for lone farmers or bandits away from roads.
  • The Inn of Illusion in Cheydinhal: During the "Where Spirits Have Lease" quest, you encounter a hostile ghost. Killing it with a weapon (not a spell) often counts as a murder for the trigger, as it's a non-essential, non-human entity.

Crucial Tip: Use a stealth attack (sneak mode with a dagger or bow) to ensure the kill is silent and quick. After the murder, do not loot the body immediately if there are potential witnesses nearby. Wait for the area to clear. You will receive no notification that this step is complete; the trigger is silent. Simply continue playing, and within a few in-game days, if your crime was undetected, the invitation will come.

The Summons: Receiving the Note from the Dark Brotherhood

Once the murder condition is met, the next stage is entirely passive. You must sleep in any bed you own or can rent (an inn bed works). After sleeping, you will awaken to find a note titled "We Know" placed on your person. This note reads: "We know what you have done. Come to the Inn of Illusion in Cheydinhal. Ask the barkeep about the Dark Brotherhood."

This is your formal summons. The note is a key item, but its mere acquisition is the trigger. The Inn of Illusion, located in the city of Cheydinhal, becomes your next destination. This step is non-negotiable; you must physically go to this specific inn to progress.

Cheydinhal is in the eastern part of Cyrodiil. If you haven't discovered it yet, you can:

  1. Fast-travel if you have visited the city before.
  2. Follow the roads east from the Imperial City or south from Bruma.
  3. Use the map to locate it; it's a major city with a distinctive, multi-tiered architecture.

Upon entering the Inn of Illusion, speak to the barkeep, Ranaline. The dialogue option "I'm here about the Dark Brotherhood" will appear. Selecting it will prompt her to direct you to a man named Gogan in the back room. This conversation is the final checkpoint before the true quest begins.

The Initiation Ritual: The "Dead Drop" Quest

Speaking to Gogan initiates the quest "Dead Drop." He is a member of the Dark Brotherhood and acts as your initial contact. He will instruct you to perform a specific, sanctioned murder to prove your skills and resolve. This is your first official contract.

The Target and the Execution

Gogan will give you a note with a name—your target. The location is always the same: the target will be found in the count's manor in Cheydinhal. For "Dead Drop," the target is Roderick, the Count's steward. Your objective is to kill Roderick without being seen by anyone in the manor, including the Count himself.

Actionable Strategy:

  1. Enter the Cheydinhal Castle (the Count's manor). It's the large building in the city center.
  2. Sneak throughout. Use the Sneak skill (press the sneak button) and move slowly. The eye icon will close when you are undetected.
  3. Find Roderick. He usually patrols a hallway on the upper floor or in a study.
  4. Wait for a secluded moment. Use the "Wait" function (T key by default) until he is alone in a room or corridor.
  5. Perform a sneak attack with a dagger for a one-hit kill. This is the cleanest method.
  6. Escape immediately after the kill. Do not linger to loot. The castle will go on alert, and you must leave before the guards block the exits.

Successfully completing this murder and escaping the city will update the quest. Return to Gogan at the Inn of Illusion to report. He will then give you the final instruction: "Sleep in any bed. The Night Mother will speak to you."

The Invitation: Meeting the Night Mother

Following Gogan's instruction, find any bed and sleep. This time, you will not awaken in your bed. Instead, you will find yourself in a dream sequence within the Dark Brotherhood Sanctuary. You are standing in a grand, candle-lit chapel before the statue of the Night Mother. The Keeper, a hooded figure, will be present. This is the iconic moment of induction.

The Keeper will speak to you, acknowledging your deeds and asking if you are ready to join. You must accept the invitation. Upon acceptance, the Keeper will perform a ritual, anointing you as a new member of the Dark Brotherhood. The dream will end, and you will wake up in your own bed. The quest "Dead Drop" will be complete, and the main Dark Brotherhood questline, "With Friends Like These...", will now be active in your journal.

The Significance of the Sanctuary

The dream is more than lore; it's a magical transportation to your new home. From this point forward, you can fast-travel directly to the Dark Brotherhood Sanctuary from your map, under the "Dark Brotherhood" location tab. This sanctuary, located in a remote forest near Cheydinhal (specifically, the road south of the city), becomes your base of operations, housing the Keeper, the Speaker, and fellow assassins.

Life in the Sanctuary: Your First Real Contracts

With "With Friends Like These..." active, your new life begins. Return to the Sanctuary and speak to the Keeper. He will assign you your first set of contracts. These are the bread and butter of the Brotherhood: sanctioned assassinations with specific targets, locations, and often, additional requirements (like making the death look like an accident or using a specific weapon).

Understanding Contract Mechanics

Each contract quest has several key components:

  • The Target: An NPC marked for death.
  • The Location: Where to find them.
  • The Method (Optional but Rewarding): Some contracts suggest or require a specific method (poison, accident, etc.). Following these often yields a higher reward and the respect of the Keeper.
  • The Cleanup: You must report back to the Keeper in the Sanctuary after the kill. He will ask, "Did you do it?" and you must confirm.

Pro-Tip: Before accepting a contract, read the journal entry thoroughly. It often contains clues about the target's routine and location. Use this information to plan your approach. Always scout the location first in sneak mode to learn patrol paths.

Advancing the Ranks: From Initiate to Silencer

The Dark Brotherhood questline is structured around five main ranks, each unlocked by completing a set number of contracts. Progression is linear and tied to speaking with the Keeper after major milestones.

The Rank Structure and Key Quests

  1. Initiate: Your starting rank after the induction dream. Complete 3-4 standard contracts.
  2. Associate: After several contracts, the Keeper will send you on "A Matter of Honor," a quest involving a duel. Success promotes you.
  3. Journeyman: More contracts. The pivotal quest "Whom Gods Annoy" follows, involving a Daedra Prince (Sanguine). This is a major, multi-stage quest with unique challenges.
  4. Expert: Continue contracts. The quest "Bad Medicine" then "Sanguine's Reality" (the conclusion of the Sanguine plotline) occurs.
  5. Master: The final rank. After completing the previous quests, you will be given the ultimate test: "Hail, Sithis!" This is the final, story-critical quest that concludes the Brotherhood storyline and determines its fate.

Important: You must complete the quests in this order. Do not skip or ignore the story quests ("A Matter of Honor," "Whom Gods Annoy," etc.) when they become available, as they are gated behind your rank and are essential for progression.

The Ultimate Reward: The Ultimate Power

Completing the Dark Brotherhood questline, culminating in "Hail, Sithis!", grants you immense, unique rewards that are worth the dark journey.

Tangible and Gameplay Rewards

  • The Blade of Woe: An enchanted dagger that does massive damage and has a chance to instantly kill. It is a guaranteed reward from the final quest.
  • The Ebony Blade (Umbra): If you choose to spare the final target, you will receive this powerful, life-stealing two-handed sword instead. This is a critical choice with lasting consequences.
  • The Spectral Assassin Summon Spell: A powerful spell that summons a ghostly assassin to fight for you. Obtained mid-questline.
  • The Sanctuary: Your permanent home, with vendors (the Keeper for supplies, the Speaker for equipment) and storage.
  • Unlimited Contracts: After the main questline, the Keeper will offer infinite repeatable contracts, providing endless gold and stealth practice.
  • The Title of "Silencer": The highest honor in the Brotherhood, a mark of your lethal prowess.

Common Pitfalls and How to Avoid Them

Many players fail to trigger or progress the Dark Brotherhood due to avoidable mistakes. Here’s how to ensure success:

  • Mistake: Killing an essential NPC or a guard.
    • Solution: Only kill non-essential, isolated targets. If a guard catches you murdering, you will fail the trigger or contract. Use stealth religiously.
  • Mistake: Getting arrested after a murder.
    • Solution: If a crime is detected, do not go to jail. Load a previous save. A bounty will permanently block progression for that contract.
  • Mistake: Not sleeping in a bed after the first murder.
    • Solution: The "We Know" note only appears after you sleep. Force yourself to rest at an inn or in a rented room.
  • Mistake: Looting the body in "Dead Drop" and getting caught.
    • Solution: Kill Roderick, then immediately sneak out of the castle. Do not stop to take his items. You can return later when the alert has worn off.
  • Mistake: Ignoring the Keeper's story quests.
    • Solution: When the Keeper has a special dialogue option (usually after 2-3 contracts), speak to him immediately to trigger the next story quest.

The Philosophical Allure: Why Join the Dark Brotherhood?

Beyond the mechanics, the Dark Brotherhood offers a unique role-playing experience. It forces you to confront morality within a game world. You are not a hero saving the day; you are a tool of a mysterious, ancient cult. The quests are often more personal and narrative-rich than the guilds, featuring memorable characters like the cheerful yet deadly Lucien Lachance and the enigmatic Speaker. The atmosphere of the Sanctuary—quiet, reverent, and shadowy—is unparalleled. Choosing this path means embracing a darker story, one where your actions have weight and consequence, and where power comes at the price of your soul.

Conclusion: Embrace the Shadows

Joining the Dark Brotherhood in Oblivion is a deliberate, multi-stage process that rewards patience, stealth, and a willingness to delve into the game's darker corners. It begins with a single, unseen act of violence and culminates in a confrontation with the very forces of Oblivion. By following this guide—making your first kill undetected, heeding the note, completing the "Dead Drop" ritual flawlessly, and faithfully serving the Night Mother—you will unlock one of gaming's most iconic and satisfying secret societies. The Path of the Night Mother is open to those brave enough to walk it. Now, go forth, initiate. The Keeper awaits your report. Remember: "We are the blades in the dark, the unseen, the unheard. We are the Dark Brotherhood."

Oblivion Remastered: How To Join The Dark Brotherhood
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