With Friends Like These Skyrim: Complete Quest Walkthrough & Choices Guide (2026)

Few quests in Skyrim throw you into such immediate moral ambiguity as “With Friends Like These.” One moment you’re sleeping in any bed across Tamriel, the next you’re waking up in a dank shack with three hostages, a masked assassin, and a choice that determines whether you join one of the game’s most infamous factions. This Dark Brotherhood initiation isn’t about solving riddles or slaying dragons, it’s about deciding who lives and who dies, and whether you’re willing to cross that line at all.

This guide breaks down every angle of the quest: how to trigger it, what each captive’s story reveals, the mechanical and narrative consequences of your choices, and what rewards await once you make your decision. Whether you’re roleplaying a righteous paladin or a cold-blooded contract killer, understanding the full scope of “With Friends Like These” ensures you won’t miss critical loot, quest branches, or the alternative path that most players never discover.

Understanding the “With Friends Like These” Quest

“With Friends Like These” serves as the gateway to the Dark Brotherhood questline, one of Skyrim’s most memorable faction arcs. Unlike guild quests that require you to walk through a front door and sign up, the Brotherhood comes to you, violently and without warning.

Quest Prerequisites and How to Trigger It

To start “With Friends Like These,” you first need to complete “Innocence Lost,” the quest that begins in Windhelm. Aventus Aretino, a child performing the Black Sacrament, tasks you with killing Grelod the Kind at the Riften orphanage. Once Grelod is dead (by your hand or through creative NPC manipulation), return to Aventus to complete the quest.

After finishing “Innocence Lost,” the trigger is deceptively simple: sleep in any bed. It doesn’t matter if it’s an inn, your player home, or a bedroll in a bandit camp. When you wake, you’ll find yourself bound and teleported to the Abandoned Shack north of Solitude, specifically northwest of the city near the coastline. There’s no way to avoid this encounter once you’ve slept, the Dark Brotherhood doesn’t take no for an answer.

One important note: if you’re playing with mods that alter sleep mechanics or radiant quest triggers, this transition might glitch. Vanilla Skyrim (as of the Anniversary Edition and Special Edition through 2026 patches) handles this seamlessly.

Your Role in the Dark Brotherhood Initiation

Astrid, the leader of the Dark Brotherhood’s Falkreath Sanctuary, has kidnapped you to test your worthiness. She’s not interested in your combat skills or speechcraft, she wants to see if you’ll kill on command. The setup is brutal in its simplicity: three people are bound in the shack, one of them has a contract on their head, and you need to figure out which one deserves death.

Except here’s the twist: Astrid never actually tells you which captive is the real target. The entire scenario is a psychological test. Your willingness to kill, not your detective work, is what matters to the Brotherhood. This reveals the Dark Brotherhood’s philosophy in microcosm: contracts are fulfilled, details are secondary, and mercy is a luxury assassins can’t afford.

The quest sits at the intersection of gameplay and roleplay. Mechanically, you’re choosing one of four outcomes. Narratively, you’re defining your character’s moral boundaries and deciding whether the Brotherhood’s code aligns with your playthrough.

Step-by-Step Walkthrough: The Abandoned Shack

The Abandoned Shack is sparse by design: stone walls, a single lantern casting weak light, three captives bound to chairs, and Astrid lounging against a shelf with a dagger in hand. There’s no combat here unless you initiate it, and no puzzles to solve. Just conversation, decision, and consequence.

Waking Up and Meeting Astrid

You regain consciousness standing in the center of the room, disoriented but unbound. Astrid greets you with casual menace, explaining the situation: someone, she won’t say who, has performed the Black Sacrament to have one of these three people killed. Your job is to make it happen.

She provides zero guidance on which captive is the target. When questioned, Astrid deflects with dark humor, suggesting you “choose wisely” or simply “kill whoever you like.” Her tone makes it clear this is as much about entertainment as evaluation. She’s testing whether you’ll hesitate, ask permission, or simply act.

Your gear is intact, Astrid didn’t disarm you, so you have full access to weapons, magic, and shouts. The captives are non-hostile and won’t fight back. Astrid herself is marked as essential during this quest (unless you choose the alternative path), so you can’t accidentally kill her and break the questline.

Examining the Three Captives

Each captive can be spoken to before you make your choice. They’ll plead, threaten, or explain their innocence, and this dialogue is where many players try to deduce the “correct” answer. But, as mentioned earlier, there is no single correct target from the Brotherhood’s perspective.

Fultheim the Fearless, a Nord warrior, insists he’s done nothing wrong and challenges your nerve. Alea Quintus, a Breton woman, nervously defends herself and points fingers at the others. Vasha, a Khajiit merchant, calmly protests his innocence and expresses confusion about why he’s here.

You can talk to all three in any order, or skip the dialogue entirely and make your choice immediately. The game doesn’t track “clues” or provide a journal update pointing to one captive over another. This is entirely a player-driven decision, and many guides for Skyrim’s complex quests emphasize how rare it is for a game to leave moral judgment this open-ended.

Who Should You Kill? Analyzing Each Captive

The captives’ dialogue provides hints about their backgrounds, but the game intentionally muddies the moral waters. Let’s break down what each captive reveals and what the community has uncovered through data mining and NPC placement.

Fultheim the Fearless: The Warrior’s Story

Fultheim claims to be a simple mercenary who’s “never wronged anyone.” His bravado and warrior’s pride dominate his dialogue, he insists you lack the spine to kill him and dares you to prove him wrong. Ironically, this aggressive posturing makes him a prime suspect for players looking to justify their choice.

But, Fultheim’s backstory is the most innocuous. Data files reveal he’s a retired sellsword who now works as a farmer. There’s no active contract on him in any Dark Brotherhood records, and his presence in the shack is purely to serve as a red herring. If you kill Fultheim, you’re eliminating someone guilty of little more than a bad attitude.

Alea Quintus: The Suspicious Breton

Alea Quintus is the captive most players suspect. She’s evasive, nervous, and quickly tries to deflect blame onto Vasha, suggesting the Khajiit is a thief or worse. Her desperation reads as guilt, and her willingness to condemn others to save herself doesn’t win sympathy.

Community analysis suggests Alea may have been involved in petty crime or fraud, but nothing warranting a Dark Brotherhood contract. Her nervous behavior is likely genuine fear rather than concealed villainy. Killing her might feel justified in the moment, but lore-wise, she’s no more guilty than Fultheim.

Vasha: The Khajiit Merchant

Vasha presents himself as a traveling merchant caught in the wrong place at the wrong time. He’s calm, polite, and expresses confusion about the entire situation. His demeanor makes him the least suspicious, which is exactly why some players choose him, trusting that Astrid wouldn’t make the “real” target so obviously innocent.

Vasha’s background, according to game files, involves trade disputes and possibly smuggling Skooma, though nothing concrete ties him to a contract. His inclusion plays on player biases, will you trust the calm Khajiit, or assume his composure hides guilt?

The uncomfortable truth: none of them are the “correct” target. Astrid later admits (if pressed) that the identity of the contracted victim is irrelevant. The Brotherhood wanted someone dead, you delivered, and that’s all that matters to them. This moral ambiguity is core to the Dark Brotherhood’s philosophy and sets the tone for the entire questline.

Quest Outcomes: What Happens Based on Your Choice

Your decision in the Abandoned Shack determines not just the immediate outcome, but whether you join the Dark Brotherhood or dismantle it entirely. Here’s what each choice leads to.

Killing One of the Captives

If you kill Fultheim, Alea, or Vasha, any single captive, Astrid congratulates you and declares you worthy of joining the Brotherhood. She hands you the password to the Falkreath Sanctuary (“Silence, my brother”) and instructs you to seek out the hidden entrance near the road south of Falkreath.

The two surviving captives remain in the shack, and you’re free to leave. Astrid disappears shortly after, and the door unlocks. This is the standard path into the Dark Brotherhood questline, unlocking “Sanctuary,” the next quest in the chain.

Mechanically, it makes no difference which single captive you choose. Astrid’s reaction, your reward, and the questline progression are identical. The choice matters only for roleplay and personal morality.

Killing All Three Captives

If you decide to kill all three captives instead of just one, Astrid reacts with surprise and approval. She comments on your thoroughness and enthusiasm, noting that you’ve “exceeded expectations.” The outcome is functionally the same: you’re invited to join the Brotherhood, given the password, and sent to the Sanctuary.

Killing all three nets you slightly more loot (whatever each captive carries), but it doesn’t change quest rewards or dialogue in meaningful ways. Some players prefer this route to avoid leaving loose ends or because their character would show no mercy to anyone in the room.

One note: if you’re playing a stealth or assassination-focused build, practicing different kill methods on all three captives can be a useful way to test damage numbers and sneak attack multipliers, especially if you’re running specialized character builds that rely on one-shot kills.

The Alternative: Killing Astrid Instead

This is the path most players never discover on their first playthrough. Instead of killing any captive, you can attack and kill Astrid herself. She’s no longer essential once you’re in the shack, and while she’s a capable opponent (dual-wielding daggers, high sneak skill, decent health pool), she can be defeated with preparation.

Killing Astrid triggers an entirely different quest: “Destroy the Dark Brotherhood.” Instead of joining the assassins, you report Astrid’s death to a guard, who directs you to Commander Maro of the Penitus Oculatus in Solitude. Maro tasks you with wiping out the Brotherhood by raiding their Sanctuary and killing everyone inside.

This path is shorter than the full Dark Brotherhood questline (which spans over a dozen quests), but it permanently locks you out of Brotherhood-exclusive gear, the Spectral Assassin power, and Shadowmere, the unique horse. You do receive a modest gold reward from Maro, and some players prefer this route for good-aligned characters.

Important: once you kill Astrid, there’s no way to reverse the decision. The Brotherhood questline becomes inaccessible for the rest of that playthrough.

Rewards, Loot, and What Comes Next

The immediate rewards from “With Friends Like These” are modest, but the quest unlocks one of Skyrim’s richest faction storylines and several unique items down the line.

Items You Can Collect from the Shack

Inside the Abandoned Shack, you’ll find minimal loot. Astrid carries her unique Blade of Woe (but only if you kill her: otherwise, you receive it later in the Brotherhood questline). The captives carry small amounts of gold and basic items, nothing remarkable.

The shack itself contains a few minor potions, food items, and a Unusual Gem (one of the 24 Stones of Barenziah) on the shelf behind Astrid. Don’t miss it, these gems are easy to overlook and required for the “No Stone Unturned” quest.

If you’re a collector of legendary weapons, note that the Blade of Woe is one of the best daggers in the game: 12 base damage, weighs 7 pounds, and absorbs 10 health on hit. It’s essential for stealth builds and worth holding onto even if you’re not speccing into One-Handed.

Joining the Dark Brotherhood Sanctuary

After leaving the shack, head to the Falkreath Sanctuary entrance (marked on your map). It’s a Black Door embedded in a cliffside south of Falkreath, near the road to Helgen. When you approach, the door will ask: “What is the music of life?” Answer with “Silence, my brother” to gain entry.

Inside, you meet the full Brotherhood family: Nazir, Gabriella, Festus Krex, Babette, Veezara, and others. Astrid formally inducts you and assigns your first contract, kicking off the “Sanctuary” quest. From here, the Brotherhood storyline escalates quickly, involving political assassinations, the Emperor of Tamriel, and plot twists that rival the Thieves Guild in complexity.

For players interested in expanding their Skyrim experience with mods, the Dark Brotherhood questline is one of the most frequently enhanced. Popular mods on Nexus Mods add new contracts, improve Sanctuary décor, and even restore cut content from Bethesda’s original vision.

Tips and Strategies for Optimal Completion

While “With Friends Like These” is mechanically simple, a few strategies can help you maximize rewards, avoid bugs, and align the quest with your character concept.

Save Before Making Your Decision

This should go without saying, but create a manual save before you kill anyone in the shack. If you’re unsure whether you want to join or destroy the Brotherhood, having a save point here lets you explore both paths without restarting your entire playthrough.

Some players also create multiple saves to experiment with different kill methods, test sneak attack multipliers, or simply see how each captive reacts before their death. Since this quest is a major fork in your playthrough, treat it as a checkpoint.

Roleplaying Considerations for Different Character Builds

Your choice in this quest should reflect your character’s morality and build focus. Here’s how different playstyles might approach it:

• Stealth/Assassin Builds: Killing one or all captives fits perfectly. The Brotherhood questline offers some of the best gear for sneak-focused characters, including the Shrouded Armor set, Ancient Shrouded Armor (from the “Locate the Assassin of Old” quest), and Shadowmere for fast travel.

• Paladin/Lawful Good Builds: Killing Astrid and destroying the Brotherhood aligns with a righteous character who refuses to murder innocents. You lose out on unique loot, but gain moral consistency and a shorter questline that doesn’t require morally gray decisions.

• Neutral/Pragmatic Builds: Joining the Brotherhood purely for rewards is a valid choice. Many players rationalize it as “someone was going to die anyway,” and the gold from contracts helps fund other pursuits.

• Chaos Builds: Kill everyone in the shack, captives and Astrid, just to see what happens. (Spoiler: you’ll fail the quest, but it’s memorable.)

If you’re running a character who values having reliable companions like Serana or Lydia, consider how your Brotherhood membership might affect your roleplay. Some followers have no issue with assassination contracts: others might feel thematically mismatched.

Common Bugs and Troubleshooting

“With Friends Like These” is generally stable, but a few bugs have persisted across Skyrim’s many versions, including the Anniversary Edition and Special Edition patches through early 2026.

Shack Door Won’t Unlock After Killing a Captive: Occasionally, the door remains locked even after Astrid gives you permission to leave. This is usually caused by killing a captive before Astrid finishes her initial dialogue. Solution: reload a save and let her complete all her lines before attacking anyone. Alternatively, use the unlock console command on PC: open the console with tilde (~), click the door, and type unlock.

Astrid Becomes Hostile for No Reason: If you accidentally hit Astrid with an area-of-effect spell or a stray arrow, she may turn hostile and attack. Since she’s essential during this quest (unless you’re deliberately killing her), this creates an endless fight. Solution: sheathe your weapon and yield by holding the block button while not attacking. If that fails, reload.

Quest Won’t Trigger After Sleeping: Rarely, “With Friends Like These” fails to start even after completing “Innocence Lost” and sleeping. This is often caused by sleeping in a bed that’s flagged as “unsafe” or owned by a faction you’re hostile with. Solution: try sleeping in a different location, preferably an inn or your own home. If the issue persists, fast travel to a different hold and try again.

Captives Die Before You Reach Them: On heavily modded setups, scripted events can misfire, causing captives to die on their own. This usually breaks the quest. Solution: disable combat or quest-altering mods before starting the Dark Brotherhood questline, or use console commands to resurrect the dead NPC and reset quest stages.

Unusual Gem Missing from Shack: If the Barenziah Stone doesn’t appear on the shelf, you may have picked it up in a previous playthrough or in a modded game with altered item placement. Check your inventory under “Misc” to confirm. If it’s genuinely missing and you’re on PC, use the console command player.additem 0001994f 1 to add it manually.

Conclusion

“With Friends Like These” is more than just a quest, it’s a statement of intent. Whether you kill one captive, all three, or turn on Astrid herself, your decision defines your relationship with the Dark Brotherhood and shapes the trajectory of your playthrough. The beauty of this quest lies in its refusal to judge you. Skyrim presents the scenario, hands you a weapon, and steps back.

For players committed to the Brotherhood path, this quest is the beginning of a dark and rewarding journey filled with unique gear, memorable characters, and one of the best questlines in the game. For those who reject Astrid’s offer, destroying the Brotherhood provides its own satisfaction and a chance to roleplay a character who draws a hard line against murder for hire.

No matter which choice you make, the Abandoned Shack is where your character’s moral code crystallizes. And in a game as open-ended as Skyrim, that kind of player agency is what keeps us coming back, even in 2026.