Should I Join The Dark Brotherhood?

When It Makes Sense

• Good fit: You are playing a stealth-oriented or assassin-style character. The Dark Brotherhood questline is built around Sneak, One-Handed, Light Armor, Lockpicking, Pickpocket, and Alchemy. Every contract rewards careful infiltration, silent kills, and clean escapes. If your build invests in these skills, the faction provides a natural progression path, relevant trainers, and equipment that amplifies your playstyle rather than forcing you to abandon it.
• Good fit: You want access to exclusive rewards and achievements. Membership unlocks the Blade of Woe (a high-damage dagger), the Ancient Shrouded Armor set (with bonuses to bow damage, sneak, lockpicking, poison resistance, muffled movement, and one-handed damage), Shadowmere (a fast, combat-capable horse with high health), and the Dawnstar Sanctuary as a usable base. You also gain Nazir as a One-Handed skill trainer and a steady source of gold through assassination contracts.

When You Should Avoid It

• Warning sign: You are roleplaying a lawful, heroic, or morally strict character. The Brotherhood worships Sithis and the Night Mother and operates as a cult of paid killers. If your character is a noble warrior, devout priest, paladin, or Dragonborn who protects the innocent, signing on with assassins creates a serious narrative contradiction and may undermine your roleplay immersion.
• Warning sign: You prefer to preserve certain NPCs or access alternative questlines. Joining requires you to kill multiple named characters, some of whom may have families, connections to other quests, or sympathetic backstories. Additionally, joining the Brotherhood permanently prevents you from completing the “Destroy the Dark Brotherhood!” questline on that save file, so you cannot see both outcomes in a single playthrough without reloading.

Pros and Cons

Pros

• Powerful and thematic rewards. The Blade of Woe remains one of the strongest daggers available early in the game, and the Ancient Shrouded Armor synergizes exceptionally well with stealth builds. Shadowmere simplifies overland travel and can survive combat that would kill standard horses.
• Engaging storyline with strong characters. The faction features memorable NPCs such as Astrid, Nazir, Babette, Cicero, and the Night Mother, plus a plot involving betrayal, a power struggle, and the fate of the sanctuary itself. The pacing and writing provide a distinct tone from the main quest or civil war storyline.

Cons

• Mutually exclusive with the destroy path. Once you join, you lose the ability to wipe out the Brotherhood for Commander Maro and experience that questline’s rewards and narrative closure. Players who value heroic outcomes or want to collect every achievement must plan separate playthroughs.
• Content may be disturbing. Contracts include the assassination of innocents, wedding guests, and characters tied to family events. Players sensitive to depictions of murder-for-hire, familial revenge, or cult practices may find the quests uncomfortable or narratively unappealing.

Decision Checklist

• Does my current character build prioritize Sneak, One-Handed, Light Armor, and stealth-related perks, or am I playing a build that has little use for the Brotherhood’s rewards?
• Would my character logically accept assassination contracts, or would their moral code, deity, faction allegiance, or personal history make membership unthinkable?
• Am I willing to lock myself out of the “Destroy the Dark Brotherhood!” questline and any associated rewards on this particular save file?

Alternatives to Consider

If the Dark Brotherhood does not fit your character, several other paths offer comparable gameplay or rewards. The Thieves Guild provides stealth-focused quests centered on heists, lockpicking, and infiltration rather than murder, and it offers the Skeleton Key and Nightingale gear. The Companions, Stormcloaks, or Imperial Legion give martial progression and a more conventional hero arc. The College of Winterhold suits magic-focused characters, while the Dawnguard expansion offers vampire-hunting or vampire-lord paths. Finally, the “Destroy the Dark Brotherhood!” questline itself is the direct alternative for players who want to oppose the assassins rather than join them.

Final Recommendation

Join the Dark Brotherhood if you are playing a stealthy assassin, enjoy morally complex narratives, or want the unique items and companions the faction provides. Avoid it if your character is heroic or lawful, if you prefer to experience the “Destroy the Dark Brotherhood!” storyline, or if assassination themes are uncomfortable for you. Because Skyrim allows multiple characters and replaying, the most practical approach is to align your choice with your current character’s values and build, then explore the opposite path on a later playthrough.