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Can You Free the Dark Brotherhood Hostages? A Comprehensive Guide

The short answer is: yes, you can absolutely free the hostages held captive in the abandoned shack during the “With Friends Like These…” quest in Skyrim. However, the method for doing so is directly tied to your decision regarding the Dark Brotherhood questline. This pivotal moment is one of the first major moral choices the game presents, impacting not only your immediate actions but also the direction of your entire playthrough. This article will explore the process of freeing the hostages, the implications of your choice, and address common questions surrounding this encounter.

The Crucial Decision: Join or Destroy?

The scenario is this: you’ve been kidnapped and taken to an abandoned shack by Astrid, the leader of the Dark Brotherhood in Skyrim. Three individuals are tied up, each seemingly a potential target for assassination. Astrid demands you kill one of them to prove yourself and gain entry to the Brotherhood. This sets the stage for a critical fork in the road: do you follow Astrid’s orders or defy her?

Option 1: Joining the Dark Brotherhood

If you choose to comply with Astrid and kill one of the hostages (any of them), you will be accepted into the Dark Brotherhood. This initiates a long questline filled with intrigue, assassination contracts, and morally ambiguous choices. However, you will not be able to free the remaining hostages if you choose this route. They are simply left tied up in the shack, and the quest is considered completed, essentially locking you into the Dark Brotherhood path. The game assumes you have made your choice.

Option 2: Destroying the Dark Brotherhood

The alternative is to immediately turn on Astrid. Instead of killing a hostage, you can attack and kill Astrid herself. Upon her death, you will find the key to the shack on her body. This decision leads to the “Destroy the Dark Brotherhood!” questline, where you will actively work to dismantle the organization. After killing Astrid, you will then have the option to untie and free all the remaining hostages before leaving the shack.

Freeing the Hostages: A Step-by-Step Guide

To reiterate, you can only free the hostages by choosing to destroy the Dark Brotherhood. If you choose to join, they will remain tied up indefinitely. Here’s a clear process to follow:

Refuse Astrid’s Order: When confronted with the choice, do NOT kill any of the hostages.
Attack Astrid: Instead, turn your attention to Astrid and engage her in combat.
Defeat Astrid: Eliminate Astrid in combat. She is a formidable opponent early in the game, so be prepared.
Loot Astrid’s Body: Search her body for a key. This key is essential to unlocking the hostages.
Untie the Hostages: Once you have the key, use it on each of the hostages and then interact with each to set them free. This will end the “With Friends Like These…” quest and proceed into the Destroy the Dark Brotherhood questline.

The Fate of the Hostages

After freeing them, the hostages scatter, each going their separate way. None of them will play any significant role in the game afterward. While they are not crucial to the main narrative after this point, freeing them offers a sense of moral accomplishment for players who value the lives of non-player characters (NPCs) in the game.

Frequently Asked Questions (FAQs)

To provide further clarity, here are 15 FAQs related to the Dark Brotherhood hostages and their potential liberation:

Does it matter who I kill for Astrid? No, if you choose to join the Dark Brotherhood, it doesn’t matter who you kill. Astrid will not confirm or deny that they were the “correct” choice. The game is designed to leave you pondering whether any of them truly had contracts on their lives or if it was a test.
Who should you kill when Astrid kidnaps you? Ultimately, it’s up to you, but the game strongly hints that Vasha, the Khajiit, is the most “deserving” due to his confession of past crimes. However, choosing to kill none of them (and instead kill Astrid) opens the path to their freedom.
Can I free the hostages if I join the Dark Brotherhood later? No, once you agree to join the Dark Brotherhood and kill one of the hostages, the opportunity to free the remaining ones is lost. You cannot go back on this decision.
What happens if I kill all the hostages? If you kill all the hostages, Astrid will still accept you into the Dark Brotherhood, but you will not be able to free them, and no additional rewards or dialogue will result from the action.
What if I accidentally killed a hostage instead of Astrid? If you kill a hostage, you are locked into the Dark Brotherhood Questline and cannot free the others. The only way to change this is by loading a previous save before completing the interaction with Astrid.
Does killing Astrid immediately fail the quest? Yes, killing Astrid will immediately fail the “With Friends Like These…” quest and start “Destroy the Dark Brotherhood!”. However, it also unlocks the ability to free the hostages.
Is it better to join or destroy the Dark Brotherhood? This decision depends on your gameplay goals. Joining offers a unique storyline and numerous rewards, while destroying it aligns with a more moral playstyle. If you’re after achievements and all the unique items, joining is recommended, but destroying offers an interesting alternative and a different questline.
What happens if I let Astrid live? You cannot complete the main story of the Dark Brotherhood without killing her eventually. This event will occur later as part of the standard Dark Brotherhood Questline if you choose to join.
Does freeing the hostages affect the rest of the game? Not significantly. The freed hostages don’t reappear later in the game, and their release has no major impact on any storylines except for the start of the “Destroy the Dark Brotherhood!” questline.
Are the Dark Brotherhood evil? Yes, they are a group of assassins who kill for profit, generally considered an evil organization. Joining them can be considered an evil act. This is highlighted in the introduction, where you kill Grelod the Kind to get the opportunity to join.
Can you destroy the Dark Brotherhood after joining it? No. Once you become a member by killing one of the hostages, you are locked into the Dark Brotherhood Questline and cannot destroy them until the end of the questline. You also cannot return to the abandoned shack after joining the Dark Brotherhood.
Can you marry Astrid? Without mods, no, you cannot marry Astrid. She doesn’t have the necessary dialogue lines and conditions to be a marriage candidate.
What happens to the young girl Babette if you destroy the Dark Brotherhood? Babette always survives and she is an essential character (meaning she cannot die.) Her fate is not tied to the outcome of the Dark Brotherhood.
Is the Dark Brotherhood a necessary evil? No. Their purpose is murder for profit. There is nothing necessary about their existence within the world of Skyrim.
Does joining the Dark Brotherhood affect anything else in the game? No, joining the Dark Brotherhood does not affect any of the other guilds or questlines, except for the Morag Tong assassins who will target you if you’re not in the Dark Brotherhood during the Dragonborn DLC.

Conclusion

Ultimately, the decision to free the Dark Brotherhood hostages hinges on your willingness to defy Astrid and initiate the “Destroy the Dark Brotherhood!” questline. While not a quest of great significance later in the game, the ability to choose their fate serves as a pivotal moment in the character progression. Whether you choose to embrace the assassin’s path or become their destroyer, you should be fully aware of the options the game provides. So now, you know: yes, you can free the Dark Brotherhood hostages in Skyrim, but how you do it has a significant impact.

Can you free the Dark Brotherhood hostages?