How To Become An Assassin In Skyrim?

I’m doing a sneaky archer run and want to fully commit to an assassin role. Should I join the Dark Brotherhood for story, or is the Thieves Guild path better?
2026-05-05 02:20:30
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MarkBook
MarkBook
To become an assassin in Skyrim, your main goal is to join the Dark Brotherhood. You can usually trigger their quest by talking to the orphan Aventus Aretino in Windhelm, then killing one of the contract targets he mentions. After sleeping, a Dark Brotherhood assassin will visit and leave a note, starting the 'With Friends Like These...' quest to officially join. It’s a whole vibe of stealth and secret kills, which reminds me of the tension in 'The Lycan King's Assassin' where the main character is bound by a magical contract to kill a werewolf ruler, creating a dangerous game of politics and survival.
2026-08-01 08:30:30
24
Maya
Maya
Ever stumbled into the Dark Brotherhood questline by accident? I did, and it was wild. It all kicked off when I looted a random note from a dead bandit, hinting at some 'black sacrament' nonsense. Curiosity got the better of me, and next thing I knew, I was sneaking into Aretino’s place in Windhelm. Kid’s got issues, but hey, he pays well. After offloading Grelod the Kind (who totally had it coming), I took a nap and woke up in some murder cabin. Astrid’s whole 'family' schtick was weirdly charming, even if they’re all killers. The missions? Chef’s kiss. My favorite was the wedding crash—disguised as a guest, slipping poison into the wine, and vanishing before the body hit the floor. The Brotherhood’s got flair, I’ll give them that.

But here’s the thing: you don’t HAVE to join them. If you kill Astrid right off the bat, you get a totally different questline where you wipe out the sanctuary for the Penitus Oculatus. Less daggers in the dark, more righteous purge vibes. Both paths are fun, but the Brotherhood’s got better loot. Also, pro tip: invest in Sneak and Illusion magic. Muffle + Invisibility turns you into a ghost, and there’s nothing funnier than backstabbing a bandit who never saw it coming.
2026-05-06 05:55:54
6
Quincy
Quincy
Joining the Dark Brotherhood in 'Skyrim' is one of those gaming moments that still gives me chills. It starts off innocently enough—you hear rumors about a kid in Windhelm performing a creepy ritual to summon the Brotherhood. If you take the bait and visit Aventus Aretino’s house, you’ll get pulled into this dark, twisted questline. After completing his contract, you eventually wake up in a shack, tied to a chair, and meet Astrid, the leader. She gives you that infamous 'kill one of these three people' ultimatum, and boom, you’re in. The Brotherhood’s sanctuary becomes your home base, and the missions escalate from shady assassinations to full-blown political hits. The writing is so immersive, especially with characters like Cicero and the Night Mother. It’s not just about stabbing people; it’s about embracing a lifestyle of shadows and secrets.

What really sells it for me is the atmosphere. The Brotherhood’s hideout is dripping with Gothic horror vibes, and the quests often involve creative kills—poisoning a gourmet’s meal, pushing a statue onto a target, or even disguising yourself as a chef. The final mission, where you take down the Emperor, feels like a culmination of everything you’ve trained for. And let’s not forget the rewards—the Blade of Woe is a beast, and Shadowmere is the edgiest horse in Tamriel. If you’re into role-playing, this faction lets you live out your darkest fantasy with style.
2026-05-10 03:57:41
2
George
George
Want to be a proper assassin in 'Skyrim'? Here’s the dirt. First, head to Windhelm and find Aventus Aretino—kid’s in a rundown house near the graveyard. Do his quest, then sleep anywhere. Astrid kidnaps you, and after her little test, you’re in the Dark Brotherhood. Their missions are all about stealth and creativity, so gear up with daggers, bows, and poisons. The Shrouded Armor you get early on is a game-changer for sneaky types. Don’t skip the optional contracts from Nazir; they’re great for leveling Sneak. Oh, and always check targets for unique dialogue—some beg, others taunt, making each kill feel personal. The final reward, the Ancient Shrouded Armor, is worth the bloodshed.
2026-05-10 10:04:48
1
LocalRoom
LocalRoom
The Dawnguard DLC offers a fantastic armor set for this playstyle: the 'Deathbrand' armor on Solstheim. It's a light armor set with insane bonuses for dual-wielding, including a massive boost to carrying capacity. For a pirate-assassin fantasy, it's perfect. The quest to find it is a fun treasure hunt. The Dragonborn DLC also adds the 'Black Book' powers, which can further augment your abilities. And let's not forget the vampire lord form from Dawnguard—while not stealthy in itself, the vampire passive bonuses to sneaking are substantial. The DLCs aren't just add-ons; they're essential toolkits that expand your assassin's arsenal and offer new, exotic locations to ply your trade.
2026-08-02 09:02:40
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