Hope you're ready for some twists :)

Astrid: “One person in this room has a contract on their head” Dragonborn who has already sliced their way through 10 Dark Brotherhood assassins sent after them: “No Shit”

I just love how absurd it is. You’re telling me Astrid walked through my front door, snuck past my wife and kids, past my husky, past my armoured troll, past my daedric armour-wearing steward, past serana and inigo then proceeded to haul my 6’2 fat ass out the door along with my full 450 point inventory and my full dragon bone armour without waking anyone up.

The thing I hated most about the Dark Brotherhood questline was: For a "Secret" organization everyone and their Mother knew you were a member. I do hope the ES 6 addresses this issue and refrains others from knowing you are a Member of Assassins Guild in the future.

When I had this happen to me the first time, I slept after becoming the Harbinger of The Companions. I thought some Companions cutscene was loading in for a finale of the questline, but then I woke up in the shack. Super creepy to think that Astrid was able to haul my unconscious body out of Jorrvaskr past all of the members of the Companions. I ended up mauling her as a werewolf.

"So, you're a mercenary? That's cool! Is it a part-time job?" "No, it's Fultheim."

Long outdated but Lokir was the one who mentioned going to Hammerfell, the Dragonborn was NOT trying to cross the border there. Dialogue with Hadvar and Ralof both state that the Dragonborn was in fact crossing the border from Cyrodiil into Skyrim, and got caught up in the ambush.

Going by the theory that you can get out of having a contract on your head by paying back a life, the only evidence of this is the case of killing the person who put the contract on you to begin with. This means that not only is it you that has the contract on your head, the person who wants you dead is also in that cabin as well.

"Never invoke the Wrath of Sithis. To do so is to invoke the Wrath of Sithis."

The real contract was the friends we made along the way

Better question is where did Aventus get the required materials to perform the Black Sacrament

I remember being in the 5th grade when this game came out. One of my classmates at my private Christian school described this whole scene to me, and very proudly told me that he just executed everyone. That was one of the first earthly memories I have of Skyrim. Good video, man!

Little known fact: Her line of "Well done" is actually just a reference to how she ends up at the end of the questline. /s

I guarantee you're putting more thought into this than Bethseda did.

Better question: If you're like me your first contact with the Dark Brotherhood in most playthroughs is when a Brotherhood assassin tries to kill you. 1) Who wanted you dead? 2) Why would Astrid and the Brotherhood abandon the Contract to recruit you?

Note that at some point in your playthrough, someone sends an assassin after you. So yes, you can have an active contract on you when you start this questline.

Novice: Killing one of them Adapt: Killing all of them Master: Killing Astrid Legendary: Killing Astrid then kill all of them anyway.

Astrid: Plans to kidnap you the next time you sleep My Character: Laughs in Insomnia

My take was always that none of them actually had a contract on them. Astred just wanted to see if you were willing to be given a target by her and do the job because for a DB assassin that's one of the more important traits.

It's crazy how something so simple like this, can be broken down into a 40 minute video, this is why I love the elder scrolls.

"someone in this room has a contract" (looks at contract i pillaged off an assassin with my name clearly written on it) "yeah it's vasha"

Astrid: “One person in this room has a contract on their head” Dragonborn: One person in this shack is also a werewolf and extremely hungry.

I kinds thought Astrid said "good job" because she kinda knows the Nightmother wants this and feels guilt over her heretical practices and disregard for tradition. She seemed like she once was a true believer. With the fall of the dark brotherhood around her, her faith is shaken, and she becomes bitter and begins to go against everything she previously believed. She asks you to kill someone and you choose her. She accepts it as divine retribution, finally claiming her.

Considering it has already been established that Astrid has removed herself from the core values of the DB, I just assumed she made it all up... She basically tested whether or not the Dragonborn would be loyal to her. If they were she would recruit them (possibly based on their skill or just because they found a person who did the black sacrament before even the DB could). I would personally assume she merely came across the victims through her own endeavors and perhaps deemed them good test subjects.

I always get a chuckle at how the mighty and mysterious dark brotherhood uses the courier services.

I remember the first time I got picked up by the Dark Brotherhood. It took several in-game months for me to actually get picked up, because I never slept with my character, I always found waiting more convenient. However, when I finally decided to sleep in a bed, I was in a bed in Tel Mithryn. Astrid managed to sail all the way to Solstheim, travel through the ash wastes, get all the way to Tel Mithryn, take me in my sleep without Neloth (A guy who never sleeps) knowing, haul me all the way back to Skyrim, and carry me all the way to a shack deep in the treacherous swamps of Hjaalmarch.

Astrid could've said "Well done." in reference to the destroy the dark brotherhood quest line that happens after you kill her. So technically there were at least 2 people who we can confirm were wanted dead.

Honestly, my first time doing that scene, I attacked Astrid. I was role-playing a kind of brutish barbarian stormcloak character, and it felt like what he would do.😂

Who else had the "big brain" moment and just killed all of them?

There hasn't been a listener for decades Night mother: New listener, I have 264 contracts ready for you from the past few decades

I wish you'd touched on the fact that if you use the clairvoyance spell it leads you strait to the Khajiit. That at least implies that's who you're supposed to kill. Admittedly, that spell doesn't always know what it's talking about, but it always points to the Khajiit.

I like your conclusion I’m going to go with that. She wanted us to take a life to release our contract. The only hiccup is how many play throughs I’ve done where I haven’t had that random encounter before killing Grelod. But maybe the assassin took an arrow to the knee on his way and retired to a cozy guard position.

"There you are! Astrid's told me all about you. Heard she pulled the ole' "Choose your victim" gag with you. Ah, I love that one..." - Babette dialogue when you first meet her.

That awkward moment when you only sleep because you learned that was how you started the dark brotherhood quest

I really wish this quest was more involved and not just a five-minute affair. If this quest were in a game like Morrowind, for example, you would probably have to go to different cities to track down where these people are from, talk to their friends, and investigate their homes to learn more about them to figure out who is the most likely candidate, with no obvious choice available.

You know... the contract having been on the Dragonborn all along is a pretty solid theory. I've had that assassin show up while I was on my way to Whiterun for the first time and always wondered about it. That being our reason for running to Hammerfell makes a lot more sense!

Not gonna lie, first time I got the Mysterious Note and saw that hand print with the words "We know" sent chills down my spine.

"Truth is The contract was rigged from the start."

You recruitment hypothesis actually makes a lot of sense when you consider that Astrid's reasoning was you owed a life for assassinating Grelod the Kind as the contract was meant for the Dark Brotherhood. Accepting you into the guild would make you a guild member and therefore, the life would no longer have been owed.

It's a good theory but if you do the quest and use Clairvoyance, you will find Vasha is the correct choice to kill. The light points to him

Plot twist: the courier set the contract on you. He's mad he has to travel to different sides of the map and dimension to just give you just one letter each time.

Maybe, but Astrid's exact words are not "someone in this room." She says "If you turn around, you'll notice my guests...there's a contract out on one of them." Them. It has to be one of the tied three. Coincidentally, Astrid's last words "Well done.." and the fact that the storyline ends with her burned up or "well-done" is pretty funny.

Astrid at the point of the shack has already broken several tenets, else the Oculatus wouldn't have the pass phrase to enter the Sanctuary. She has invoked the Wrath of Sithis.

I fought at least five assasins before the abandoned shack scene. I knew of the contract. Somehow, it still didn't click that I was the one. Ended up killing Astrid bc I didn't want to kill an innocent person and I knew for sure that she wasn't innocent, with or without a contract.

It gets even darker when you realize the body Aventus is using is most likely his dead mother

"One person in this room has a contract on them" Me: Drops the 107 contracts on me signed by Astrid *Yes I've killed a lot of people and stolen a shit ton of things*

27:41 Isn't that what happened in the destruction of the Falkreath Sanctuary? Astrid did the black sacrament on herself and the Night Mother not only heard it, but accepted it and passed it on?

I always assumed that she meant you owed them a kill as in an enemy of the Brotherhood as opposed to a contract given to them. Vasha seemed like the logical choice.

I love how the dark brotherhood quest begins in Skyrim. Like I've gone out of my way to try and sleep on the furthest north side of Solstheim and still woke up in the abandoned shack. Astrid really went through the trouble of hulling my ass all the way from there by boat and about halfway across Skyrim just so she could have the most dramatic 'who's guilty' party ever.

Dragonborn: "Hey. Cool headgear I can't get anywhere else in game... I'll just... Kill you all..." Astrid: "had to be one of them, right?" Dragonborn: "oh yeah the contract"

I always thought they all had targets because Astrid doesn’t seem ruthless enough to kidnap potentially three innocent people. I can’t think of any dark brotherhood member in Skyrim, other than Cicero, who would think about killing someone not related to a contract ignoring the single exception for spoiler reasons. All of them put too much effort and time into the brotherhood to be unprofessional about killing. I think she brought in three people who needed to die and killed the others herself after your test.

I've watched this video so many times. It always pops up on my feed every few months, and I enjoy it thoroughly each time. Great for listening especially. Superb like your previous and works since.

If you use the spell "Clairvoyance", it point at the Khajiit. You're welcome.

Astrid: "Someone in this room has a contract on their head." Dragonborn: "It could be any one of us. It could be you, it could be me"

I usually keep a scroll of fire storm for this quest. Delivers well the message of how much i care for Astrid and her "orders". I use it without even turning to see the prisoners

Cicero could potentially have been the one to preform the black sacrament. He is favored of the Night Mother, even if she doesn’t speak straight to him (she allows the Jester he killed to laugh to him, something Cicero was extremely grateful for, after being trapped alone in his prior sanctuary for months)

The first time I killed Grelod I slept in Blackreach, much rage was had that day

Wait, I always thought that the Dragonborn was captured trying to cross INTO Skyrim. Not out of it. The way you have no ties in Skyrim before the start of the game as well as when you chose a Nord you are told it was a bad time to try to return to your homeland.

You truly outdid yourself with this one. My vote for your single best video... Picture me doing the head explosion hand gesture. Your theory actually makes perfect sense. You had the contact on you and your kill in the cabin was payment to Sithis so you could be recruited.

I suspected that none of them had the contract on them, but until now I couldn't quite tell why. Thank you for the good explanation and the background story

J.K. Rowling reveals that you, the reader, were... the contract all along.

I always thought the player character was trying to cross the border to get in, not out of Skyrim. No one's heard of you, no-one recognises you, even if you're a Nord. Idk, always just made more sense to me.

I’ve never encountered those dark brotherhood assassins. You learn something new every day!

Haven't watched this yet but my guess is it's the dragonborn and/or Astrid on account of Astrid saying "well done" if you kill her as well as the fact that you can easily get a dark brotherhood contract on you using the power of crime.

I did this quest again recently and used the clairvoyance spell in the shack, it points at Vasha

Just use the Clairvoyance spell, it always points to the cat for me.

In conjunction with the theory that there was a hit on the current standing emperor put out by an unknown agent, the Dragonborn could potentially be the only locatable decendant of the Septim bloodline, ergo "the rightful emperor", which would explain the incongruity between that particular scene and the near end of the Dark Brotherhood quest line where Astrid straight up tells you she assumed they would just kill you and stop there.

My personal theory is the player is the one with the contract, since multiple assassins can be sent after you before the quest can begin. And since you join the brotherhood, the contract is technically complete

Whispers* “I know who put the contract on us” ... “It was... Nazeem”

Like almost everyone who tried to solve this "riddle" you've made the fundamental mistake of claiming that Astrid said something ambigous like "there's a contract on someone in this cottage" what she however literally says is "If you turn around you'll notice my guests... there's a contract on one of them" so she clearly claims that one of the three has the contract on them. The mistake that most people want to make when they try to solve this riddle is that it's either Astrid or the PC that have the contract on them because if you kill her she says "well done" while the PC is ofcourse the only character who can actually have a contract on them. What however most people just ignore because they want to solve an unsolvable riddle is the simple fact that Astrid doesn't even have a listener anymore and she just uses the Brotherhood for her own gain. She doesn't take contracts from the Mother she just takes contracts that she believes makes them the most money. As Astrid herself says : It's not important who had a contract on them it's important that she told you to kill and you did without even verifying that the NightMother actually ordered the Kill in other words this was just a test wether you'd kill for her

I know this is an old video but I just learned today that if you use the clairvoyance spell the path leads to Vasha.

Your correct about the contract it happened to me early in the game after recruiting Faendel as an ally after the fifth assassin I started investigating and went back to visit faendel and discovered Sven the love rival knew what I had done and hired the dark brotherhood.just so you know sven came down with something terminal.

babette, canonically: "There you are! Astrid's told me all about you. Heard she pulled the ole' "Choose your victim" gag with you. Ah, I love that one..." im so sorry camel i think you made a 41 minute long video for a question that has no answer because astrids a liar

Alduin put out the contract on the dragonborn as a way to protect his future.

The contract is on Astrid. She already betrayed TDB before meeting you, breaking several rules laid down by sithis. If you kill her in the shack she actually says "well done" Cicero is actually there to get things back in order, since they did lose their sanctuary. He didn't have much choice, since the skyrim one is the last active sanctuary. Astrid her betrayal is the reason the guild is in such a sorry state🤷

This was one hell of a Professor Layton turn of events

I've always wanted to make a card with the Brotherhood hand and "We Know" on it's front, but "...that it's your birthday!" inside. XD

Astrid basically admitting the Thieves' Guild is more structured than expert assassins.

To me, it was always pretty damn obvious that the "Which one of these people has a contract on them?" bit was just a smoke and mirrors trick to distract the PC from the much more pressing moral dilemma of "Should I really kill a defenseless person just because some woman in a mask told me I have to?" As a bonus, the PC can pick out someone THEY think deserves to die, easing them into the idea of killing for Astrid. The victims were all chosen to reveal something about the PC's character. A PC who values bravery and honor might pick Fultheim for being a dishonest coward. One who thinks of themself as virtuous and lawful might kill Vasha in order to rid the world of a dangerous, unrepentent criminal. And one who is more selfishly inclined might go with Alea just because she's loud and obnoxious. None of the prisoners have a contract on them, else it wouldn't be possible for them to make it out of the shack alive even if you don't kill Astrid. It's all just mind games.

Genuinely Camel. You've convinced me we have the contract. Not sure if the others do, but that random encounter and border point is undeniable truth. Well done. I never put it together. I never thought about it

"all those files, all that discipline?" Sweetie there are f i v e rules. There's more rules for boiling pasta, it's really not that restrictive

I used the Wabbajack on one of them, they turned into a dremora and killed the other two, then Astrid jumped down and helped me kill it.

So I had Live Another Life installed and had my Breton character start with being left for dead in a random location. My guy woke up by Kynesgrove beside a merchant’s caravan, went on to become Thane of Dawnstar, was attacked by the DB, killed them, discovered Riften’s skooma dealer, was on my way to kill them, got attacked AGAIN, and then became Thane of Riften. Combined with Maven’s little altar, my headcanon for my character’s backstory was he was the only survivor of a Black-Briar hired raid on a merchant caravan, and Maven wanted him eliminated so nothing could be tied back to her. When he was spotted in Riften, she hired another one. When he returned and was named Thane and didn’t immediately recognize nor attack the Black Briars, she realized he didn’t know anything and so retracted the contract on his life. Of course, he kept the notes and went on to destroy the DB single handed. But that’s not her problem anymore.

Playing the dark brotherhood for the first time as a morally grey character. I normally don't RP, but after so many years I wanted a change. When you look at the dark brotherhood from a "family" POV, it's rather weird. Astrid has clearly picked you out for the organization. In a sense, you have a contract on you (And you can have other contracts on you too, of course but this is more family related. Like a cult wiggling it's way in). Astrid has chosen you and the reward is your membership. But I also do think she has her own contract on her head. Perhaps a marking from the mother herself lmao.

Astrid: "hey you, you're finnaly awake..."

WARNING! Spoilers Ahead: If you follow the entire Dark Brotherhood chain to the end, you learn that Astrid betrayed the Brotherhood to the Penitus Oculatus in violation of Tenet Number 2. She also admits that they have stopped following the 5 tenets and have decided to do things their way violating Tenet number 1. She directs you to steal Ciceros Journal, which, although the player steals it, they do so under the instruction of a superior which violates Tenet number 4. She also directs you to later kill Cicero which violates Tenet number 5 (justification as per the previous violation). All of these violations invoke the wrath of Sithis who is essentially the ultimate authority of the Dark Brotherhood, and thus able to put a contract on Astrid. Since the player later becomes the listener, it can be postulated that Sithis, through his Daedric power has manipulated the fate of the player to put them in the position to carry out the contract on Astrid. The player is not in any violation of the tenets as they are not a true member yet. Also, when the Penitus Oculatus destroys the sanctuary, Astrid willingly admits she has broken the tenets of the brotherhood, and has invoked the black sacrement on herself.

When meeting babette in the sanctuary for the first time she says "I heard Astrid pulled the ol choose your victim gag, love it"

One flaw in the reasoning here, Astrid wouldn't care about fulfilling your life debt. She doesn't follow the tenants, so Sithis isn't her concern. Rather, it's to see if she could get you to kill for her, even if you had no real cause to kill the target. You had reason to kill Grelod. She was evil and deserved it. So it's hard to say if you'd make a good murderer or not. But these three, you don't have a reason. Other than being told to do so.

Personally, I think Alea Quintus, the supposed mother of six children, is lying about her identity. Whether she is the contract or not I have no idea, but she is definitely not who she says she is. First, she is a Nord with an Imperial name. Odd, but not damning. Until you realize that Quintus is only ever used as a first name in the Elder Scrolls (yes, I checked UESP across all the games), NOT a last name, implying that Alea is trying to pass for an Imperial but isn't familiar with Imperial naming conventions. And/or she chose her name for it's meaning (see below). Secondly, Alea's name has a rather interesting meaning. Alea means "a risk, chance, venture, or game of dice", while Quintus has the less interesting meaning "fifth". So her name literrally means "fifth game of chance" or "fifth risk". This, along with her tone of outraged annoyance when you speak to her, suggests she might be more familiar with this sort of predicament than she lets on. Thirdly, in the game files her class is set as a warrior. And odd profession for a supposed single mother of six children. When, as she so often likes to remind us, would she have time for such a thing? Fourthly, a mother of six children is an awfully risky kidnap victim. Astrid's other kidnapees make sense because most won't care or notice that a murderous thief and a sell-sword have gone missing (indeed, plenty would probably be pleased, even among Vasha's supposed gang). But a mother of six children? That's six people who will miss her immediately, stand witness to her disappearance, and, because someone has to take care of them, give people reason to go looking for her, not to mention the high chance that one or all of the children would be near Alea at all times and see Astrid. It just doesn't make sense for Astrid to draw that much potential attention to herself and the Dark Brotherhood for no pay, especially since Commander Maro knows Astrid's identity and has long "watched the Dark Brotherhood's movements... waiting for the time to strike". Astrid's choice makes far more sense if Alea isn't actually a mother and is hiding her real identity behind an assumed name and sob story meant to make you feel sorry for her. Astrid likely knows or guesses that Alea Quintus isn't her prisoner's real name and certainly knows she has no children, but doesn't care what story Alea tells so long as you end up killing one of the three. Who is Alea Quintus really? Not the slightest, but she obviously works in a profession where secrecy is key. Or where her real identity would make people want to kill her more.

13:17 Of course Fultheim lives in the middle of nowhere, it's not like he could live Elseweyr

If you use Clairvoyance (the spell used to direct the player to the current goal) it will point towards the Khajiit

28:15 They don't need to both find out the same way. Astrid says they find out. There's a few ways it could work. Firstly, since she already broke the rules the Night Mother is fine with killing her. Secondly, there's the idea that the Dark Brotherhood is beholden to all contracts done properly and it's just never been figured out that they have a glaring weakness. That could be the cause of the radiant quest targets: a buildup of unfulfilled orders. Thirdly, Sithis is and could know the future, so he approved it. With any of these, Astrid could just have heard someone put it out on her and proceeded to laugh her ass off and ignore it. All of them were bending or breaking the rules to some degree. So, it's quite possible that since they had no guidance they unilaterally agreed they don't take contracts against each other.

Can we take a minute to appreciate how good the voice acting for Aventus was? Especially for a kid.

Given her reaction, I always assumed she was lying and none of them had a contract on them. Thats why she doesn't care who you pick, there is no circumstance in which she has to worry about you letting someone with a contract on them walk away. It also matches up with her reply that it doesn't matter and the only point was seeing if you were someone who would be willing to kill on command.

I always thought it was all 3 of them that had the contract. It doesn't matter who you kill, once you left astrid would finish the others off and fullfil the contracts.

That headcover looks kinda slick though, fits the "i give you peace so rest in peace" gameplay for me

Maven definitely seems like the kind of person who would take a contract on Astrid for failure

*astrid fight will be hard* me sleeping for the first time at lvl 80 me: curb stomps astrid with my bare hands

On the topic of the Dark Brotherhood contract against the player character. I don't know if I just had a mod when I saw it, but if you brought the contract to Astrid, there'd be a dialogue that basically said "Hey, why the fuck did you send assassins against me?" And she'd say something about that. I don't even know if that was vanilla dialogue, but I do remember it happening.

Fun fact: if you use Clairvoyance, which points to quest objectives, it points to the Khajiit.