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This time, instead of killing the Khajit again, I decided to take out Astrid instead. And now her last words - "Well Done!" have made me paranoid and insomniac.

Did I play into her hands by killing her? Did the Dark Brotherhood leaders in previous games ritualistically say the same thing upon getting killed (I don't think they did in Morrowind, but it's been a long time since I played it)? Or is this something she would have said if I had killed somebody in her presence, only this time that "somebody" was herself (which means this is a bug)? Most importantly, for my newly wed bride awaits me: is it safe to sleep?

A lot of other people all over the internet seem to be expressing the same doubts and uncertainties, yet no explanation has come forth.

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    You have killed the Khajit in the past? Heck, I'll frequently Fireball the lot! In any case, killing Astrid instead of one or more of the "victims" puts you in a position to help the Penitus Oculatus wipe out the Dark Brotherhood. It's a shorter, less rewarding quest than joining them, but I've done it on my more "scrupulous" play-throughs. – tjd Oct 28 '15 at 16:16
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    I'd have to check something to see if this is right, so I'm not posting it as an answer, but at the end of the Dark Brotherhood quest you kill Astrid at her command, so it would make sense for her to say "Well done" at that point. Perhaps she's just scripted to say that when she dies, assuming that she'll be killed at the end of that quest. – DCShannon Oct 28 '15 at 18:16
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    @tjd Last time, I created fire runes under each of them. Saw a nice display of ragdoll physics and Havok engine when the explosion lifted and threw them. – strNOcat Oct 29 '15 at 8:20
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    @DCShannon Yes, this seems more likely. I guess I'll dive in CK and try to see. – strNOcat Oct 29 '15 at 8:21
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This is highly speculative. I don't think there is an actual answer to this question.

However, I think it's simply because you did what she said. Loyalty means everything to the dark brotherhood, which is stated in a few books about the dark brotherhood. She said, that a "sacrifice would be required to join the dark brotherhood", so you have to kill somebody in the room, but who that somebody is, well, she left that choice to you. I think she thought about that risk, she wouldn't want to invite someone to the dark brotherhood who's stupid. She took the risk, got her ass whooped, yes, but you did the job, therefore she says "Well done".

On the other side, this is just my theory ... I mean, nobody could tell you where the dark brotherhood hideout was. Also, she loved the Dark Brotherhood, and she loved the leading position, so the death of her and her "family" surely wasn't her intention.

But as mentioned, there is no real answer to the question. However:

Most importantly, for my newly wed bride awaits me, is it safe to sleep?

Yes, it is. There won't appear any random assassins disturbing your honeymoon nights :P

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    This answer seems to be correct: There are two separate Astrids according to CK: Astrid and AstridEnd (the roasted version). The original Astrid's death line in DB quest is "Well Done..." while generic one is "Aghh.." (fallback line to be used if I/somebody killed her outside of questline). However, in AstridEnd's case, the DB quest's death line is "Uhh.. thank you..." while generic line is still "Aghh..." This pretty much rules out any possibility of bug, since Bethesda explicitly recorded the "Well done..." line for Astrid only (not AstridEnd) and therefore, must have put it their purposeful – strNOcat Oct 29 '15 at 15:04
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I feel dirty posting a link to Yahoo answers, and in this case for good reason: this answer claims to have come from "Elder Scrolls Lore books" and yet none of the text garners a Google hit other than the answer on Yahoo answers itself:

"Astrid was allowed to join the Dark Brotherhood only once she had proven herself to show absolutely no emotions. To prove this, when Astrid was told to behead one of three criminals, of whose crimes she was told, she instead beheaded all three. Thinking this would prove of her emotionless personality, she returned to her recruiter and found him displeased." ...

"After some time her recruiter explained to her that she was being tested on whether or not she could discern who, in a group, deserved the most punishment. By beheading all of them, she had failed to set her own standards for what she herself considered punishable by death. This, in turn, showed that she used her emotion of desire and her need to please to direct her actions."...

"She would later use the same induction rite that she was given onto her new inductees. She would bring in three people that had committed different degree of crimes. However, she still found herself to have committed the greatest of crimes; she had used her own emotion to determine how she would pursue her directions."...

In summary, this is why she says "Well done." It is because the player, in her eyes, killed the person who had committed the greatest crime and deserved death over the others.

The uesp wiki's dark brotherhood lore book list contains no references to Astrid other than Cicero's Journal, which is unrelated to the text above. If anyone knows where one could find the text above I think it would help.

In the meantime this makes sense, but for all I know some guy on the Internet made it up.

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    Only thing related to her initiation in DB seems to be what she herself tells the player: "...I had an uncle, you see. He made certain... unwanted advances. So I killed him. And liked it. Then I killed again. And liked it even more. And so on..." I'd say her masters would had been less worried whether she could carry out contracts and more about if she'd simply kill her new 'family' too just for lulz. – strNOcat Oct 29 '15 at 8:26
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Occam's razor; it was pretty obvious to me, at the time, that she was commending your combat prowess with her last breath.

You've just slain the leader of the Dark Brotherhood, arguably the most skilled assassin at the time... Well done.

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remember her question? one of the people in this room is a KILLER AND HAS A CONTRACT ON THEM. Aka the 3 in front of you are innocent. when you kill her she literally saying well done because you killed the right one.

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    Astrid doesn't say "one of the people in this room is a KILLER AND HAS A CONTRACT ON THEM". She says "One of these poor sods has a contract out on their life". No mention of being a killer. – Wrigglenite Mar 27 at 17:33
  • Close enough but you get my drift – RayvinMadoki Apr 10 at 20:01
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    No, I don't get your drift because what you're saying makes no sense when the quote is wrong. Even disregarding that, the "Astrid is the right choice" theory was mentioned over three years ago, so this post brings nothing new to this question. – Wrigglenite Apr 10 at 20:08

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