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Elder Scrolls IV: Oblivion- Dark Brotherhood (Black hand) Quests and Ranking Guide
Cheydinhal Abandoned House
Who is Sithis, you ask? Sithis is the 'leader' of this guild. The Dark Brotherhood. He tells us who to kill and we should abide by his rules. Much of this guild is assassinations, in fact there are few quests that don't involve a murder. Do not be deterred from this guild if you think it will just be about killing people without being seen, as many of the contracts are designed to test your skills in the art of silence and sneaking. It is (in my own personal view) the thieves guild, but with murder instead of theft. You have a complex path to get to your intended target and you can't let anyone see you (except the target can as long as they don't alert people). But wait! There's more, in fact there is also a bonus attached once you do the first few quests that give you magical weapons and gifts that will help you in the future quests or just in general.
So now that you know the guild isn't just slicing people up because you're being paid to, continue reading on for my guide through the ranks, basic murder techniques, tips and hints for things you should do before you start going after each person, how to even get in without incurring a bounty, and much more! Get your ninja pants on, this is going to be a silent, thrilling, bloody, adventure. (If you don't own ninja pants, it's okay, I did fine with normal pants on and even shorts.)
The Basics for Murder, an Assassin's Guide
There are many ways to go about murdering someone, without being seen. While the armor and hood the Dark Brotherhood awards you with after your first quest is helpful, it isn't available till you complete the first quest. I'm going to list some basics and then go into detail on some others as I think of them.
- Poisons- great way to level up alchemy skill if you make them yourself, but it may not do the job without a sneak increase. (Assuming your potion making skill is in the lower quality, better poisons will almost certainly do the trick, especially with sneak boost.) If this gets you an assault charge, just charm a guard real quick to try to yield to him, he may even pay the fine for you.
- Magic- Cast a frenzy spell if your target is near people, anyone they attack will help join in on the fight, just make sure they attack you first or let everyone else do it for you.
- Poisoned Apples- Right out of a fairy tale, you can buy poisoned apples from M'raaj-Dar once you are in the Dark Brotherhood or take some from the barrel in Fort Farragut. They cost 300 a piece but allow you to kill without getting your hands dirty, just reverse pickpocket them when nobody sees you and they will eat it (though it may take a few days).
- Enchanted Items- If you have access to the enchanting table and some soul gems, make an item that has 0 weight (a Mage's Hood for example) that does damage to self. Name the item with some A's at the beginning or take any hood items they have in their inventory when you reverse pickpocket them and they should put it on when they wake up. If you talk to them after you put the hood in their inventory they should put it on and then go back to sleep, or you can wait for them to wake up and do it themselves.
- Use Others- I mentioned the frenzy spell to get people to attack you, but you can also use companions to do the murder for you and you don't get the bounty for murder. (You may get an assault charge depending on how you go about it though.)
Murder Rank- How to Join the Dark Brotherhood
Before you go off in search of contracts and start your career as a hired killer, you have to kill someone. Whoa, put that weapon away! Not just anyone will do (technically this is true but I'm going to tell you a few people that don't get you a bounty). You see, the Dark Brotherhood has to know you will do well murdering people for a living, so you can't just walk in and ask to join like the Fighters or Mages Guilds (and kinda thieves). As long as they are non-essential you could kill any of them, including quest NPCs, but there are some specifics you can keep an eye out for, or find yourself.
- Glenroy- Near the end of the tutorial he becomes non-essential and you don't get a bounty. He's the male guard that isn't left alive at the end a.k.a. Baurus (if you have already played you know who he is).
- Agronak gro-Malog- The Grand Champion of the Arena, if you do the Origin of the Gray Prince quest his death counts as a murder and you don't get a bounty. I have a hub on the Arena rounds, so if you want this route I can advise you a little. Good for beginners as the gold rewards for the Arena aren't level-dependent.
- Alga- She lives in Bruma, and can be found in Olav's Tap and Tack or Honmund's House. She also respawns so you don't have to worry about making any NPC disappear forever, although the previous two die anyway.
- Alval Unvani- This guy likes to travel so he can be found along roads, making it so there aren't any witnesses. He is also part of a later Dark Brotherhood Quest so killing him is like killing two people with one blade swipe. He lives in Leyawiin (Sundas only), but can be found in Bravil on Morndas/Tirdas, Skingrad on Middas/Turdas, and Bruma on Fredas/Loredas. (He may take a bit to get there, always in an Inn so keep an eye out.)
- The Skooma Den in Bravil has 4 residents inside with low responsibility so killing them will most likely go unreported and thus, no bounty.
- Arena Foes- Just use a fear or demoralize spell that won't incur a bounty either.
- Arnora Auria- After Jorundr tells you to kill her, don't talk to her and just kill her quickly. You finish the quest, no bounty, and the dark brotherhood will come to you.
- Caminalda- When you are doing the Anvil Recommendation quest if you kill her before she attacks you it will count as murder without getting a bounty.
- Camonna Tong Thug- Kill one of the two before they attack you, so use a bow from a distance or sneak. They also respawn after a few days. (They are at Walker camp)
- Mephala Daedric Quest- It requires you to murder two people and frame them for each other's death. Mephala is related to the Dark Brotherhood, so this is probably why it initiates the Dark Brotherhood invitation.
- Umbra- Normally killed during Clavicus Vile's quest, you can kill her at any time to complete the main quest and get an invitation to the guild. *Warning that you may not get xbox achievements if you complete the main quest this way*
- Glarthir- Kill him behind the church to end his stupid quest and get the bounty free murder. (You might wait till he has you do the murders at the end if you want the gold, he also has some good stuff in his house if you feel like trespassing.)
- Respawning Followers- You can get in this way but keep in mind you will most likely be suspended from whatever guild you are using them with.
- Non-Hosile Adventurers- They have a low chance of appearing in dungeons, one is Dzonot Cave, on the City Isle, but not always appearing there. Probably not the best option this is, unless you happen to find one when reading this or something.
So you just have to kill someone but keep in mind that some NPCs can't be killed and some deaths will bug/kill/prevent quests from finishing. Any quest NPC that you know will attack you, but you kill before they become hostile will probably work, although I can't test every option out there. When it says someone has witnessed your murder, then you will get your invitation the next time you sleep.
In order to become a slayer you have to complete three quests, A Knife in the Dark, A Watery Grave, and Accidents happen. They are all fairly simple, and you even get to use that brain of yours to find the best course of death.
A Knife in the Dark is the first Dark Brotherhood quest and my favorite for reasons you may not guess. Basically you have to go inside of the "Inn of Ill Omen" (reason 1: That name is awesome) take a left and go downstairs to find the target. His name is Rufio, and he is sleeping (at least he is for me, apparently not always although I've yet to see him awake). If you talk to him and learn of his past you can infer that he was part of an attempted rape that ended up killing the victim (reason 2: that guy deserves to die). WAIT! Reason 3 occurs before you kill him. If he is asleep, you can use this room to level up your sneak (and by level it up, I mean by A LOT). I went from 48 or so all the way up to maybe 59 or 61 without any added skill from armor or items or whatever. It takes awhile to do so, but if you walk reaaaalllly slowly across the room you should get a couple increases per crossing (if you go the long way and go as slow as possible while moving). I usually do this until I get bored or I have to pee, but do it or not its up to you. Swipe at his sleeping body (while in sneak for extra oomph) with your new blade of woe, or another weapon/spell of choice and find a bed to sleep in to have Lucien welcome you to the Family. (You can sleep right there in Rufio's bed if you want, push him off if you feel weird and he didn't fall off himself.) Lucien also tells you about the Abandoned house in Cheydinhal and the password for the door, once inside talk to Ocheeva to get your reward.
Next you get your contracts from Vicente (A vampire, ooh). First off you have to kill pirates (awesome!) or at least just the captain, but most ways to go about this quest involve other deaths as well. It's called A Watery Grave and as I just hinted at, there are many options to go about this quest and you learn of one if you speak to your sisters and brothers. You can hide inside the crate at the end of the dock area thing and make your way to the captain's cabin, killing a few pirates along the way, OR you can just kill all the pirates you see and probably make the guards attack you and cause a huge scene, OR you can wait until night has arrived and jump onto the balcony and pick the lock to get inside the captain's cabin directly. You probably can't kill him with one blow, but make sure he doesn't alert his fellow pirates, make sure you loot his body and chest and grab the nirnroot in his room. Leave through the back door of the cabin either way and run away or fast travel. Two pirates will come in after you kill him (though you have a warning knock) so if he is asleep you should loot his stuff before killing him to gain some time or you can hide in the shadows near the door where the pirates enter if you don't want to escape or don't have time to.
Lastly you have Accidents Happen, which you might guess has to do with making something (a murder) look like an accident. This is the beginning of a glorious set of quests that give you an optional bonus (recommended as they usually help you out later on and they are at least useful to get some money if nothing else). This quest is again given many options, although not so much with how the result is as how you go about doing it. If you choose to do the bonus, making the head fall on the target's head and leaving his manservant Gromm alive, then you should wait for 8-11 pm although the mid range is best to give you time to get there. Sneak in through the back door in the basement to avoid Gromm seeing you, and use the shadows to sneak upstairs (to the first floor and then the second). Once you go up the stairs to the second floor the room directly to your right is the entrance to the head's fastenings. Make sure Gromm doesn't see you (although he saw me for a split second the last time I did it), then open the crawlspace door and loosen the fastenings (you can also wait in there till the time frame if you want to, just close the door first). You should hear Baelin die and Gromm will then be defensive so make double sure he doesn't see you sneak out the way you came. If you get the bonus you receive Sufferthorn, an Elven Dagger that damages Health and Drains Strength.
To obtain the rank of Eliminator you must complete two or three quests, Scheduled for Execution, The Assassinated Man, and possibly The Lonely Wanderer if you failed the Assassinated Man. The failure of The Lonely Wanderer doesn't remove you from the guild, but it does make Vicente quite upset with you. The Assassinated Man is the last quest you get from Vicente Valtieri, and you get the well key, so best complete it without failing.
Scheduled for Execution is a quest I was hoping I would get to do from the very beginning. You see, nobody told me there would be a jerk in the cell across from me that would say snide comments and try to hurt me. After quite a few characters to find a race that I like, he got a tad bit under my skin and I wanted to kill him (please keep in mind I wouldn't think this in real life, just in video games, I'm not a murderer lady). When I then joined the Dark Brotherhood I was distracted by the other murders that I got to commit and help people with. Then I got this quest, and my eyes watered to the point I thought I would cry tears of joy. You have to sneak into the Sewers and kill the same person that was a jerk in the very beginning moments of the game, Valen Dreth. Getting through the Sewers themselves isn't all that difficult, there's a few rats, crabs, and goblins but no people until you reach the area you saw the Emperor get killed. Here, you have to sneak past the guards and stick to the shadows. If you need a visual, this is the video I used my first time. Since the bonus is to go through the entire Sewer system without killing any guards you may want to watch it if you're having issues. I'll try to tell you in text here though as a reference. The first room you want to wait for the men to stop talking, a detect life spell or (better) enchanted item (you can buy the eye of sithis from M'raaj-Dar before you leave) will help you out immensely. Once you get past that first mini hallway you are in the room where the last set of Mythic Dawn attacked and killed the Blades except Baurus, go to the far end of the room, avoiding the guard that keeps post in the center line of the room. make sure they are facing away from you (towards where you want to go) and sneak onto the center path, if they are facing you hide behind the pillar until they turn around. Go up and open the door, keep an eye on the guards though and trust your instincts, don't follow me if you don't think you can do it. Also a good idea to save once you get past each door or a difficult area so you don't have to do it again. Again, stick to the shadows, and quickly go along the right side and past the area of light into the shadow corner. If the guard with the torch is already making his way towards you STAY, don't go into the light. Wait for him to go away from you again and when it's safe to do so, follow him. If you stuck in the shadowed corner he will see you when he comes back towards you so sneak behind him and go through the path while he's still walking away from you and hasn't turned to go back down the hallway (he must be walking towards where you entered in other words). Make your way through the area until you reach a wooden door with another door a little further ahead. If you are worried about the guard finding you, shut the door behind you. After the second door you are now in the room the Emperor and his guards first left you in, the one that the rats attacked you in. No guards so just make your way up and you should know the way back to your old cell from here unless you forgot. Just go through the door and stop just before you enter your cell. You should hear a conversation between a guard and Dreth, wait for it to be over and the guard SHOULD go up the stairs and leave the room, leaving the two of you alone. If he doesn't just try moving forward a bit, without being seen (this is where some life detect could be useful, watch for his blob to move away and disappear). Once he does leave though, grab the keys from the table at the end of the room if you want to open Dreth's cell and kill him, warning though he will go running through the sewers and you could end up killing a guard. I would use destruction magic or a bow to kill him without opening the door unless you think you can kill him in one hit, talk to him if you want him to be afraid of the night mother and such. I would, cause he's a jerk. Once he's killed you can take the key off the table to leave through the front door and, since its public, you don't get any bounty or attack from the guards. Or you can return though the sewer and risk killing a guard again. Either way, return to Valtieri for your reward(s). The bonus item is Scales of Pitiless Justice, scales that increase strength, agility, and intelligence but reduce personality (all by 2 points). It only does so when its in your inventory so I usually have mine on display in my house (if I own one by then).
The Assassinated Man involves the staging of an assassination and doesn't even have a murder to commit, sad. You do get to pretend to kill someone though and you get to kill some zombies of people, if those count. This guy, Francois Motierre, has a debt and are sending someone to kill him so you have to use a special blade to stage the killing of Motierre when the enforcer arrives. So talk to him and then knock, knock, in comes Hides-His-Heat, swipe at Motierre with the special blade to "kill" him and flee Chorrol. Now you have to wait for an entire day to get his body from the Chapel under-croft so wait or do some other quests if you have any nearby. Once the 24 hours are up, go to the under-croft and activate his body to wake him. He then warns you that his family is buried there and they may take his revival as a sign of disrespect. Make sure he stays alive, since this is the only quest in this line you can fail, and slay the three zombies. One way to avoid them is to quickly get to the door after you wake him up, before he talks to you, then you can just leave after the zombies come to live and they shouldn't follow you. Next you have to go to the Grey Mare Inn so he can buy passage out of Cyrodiil, and return to Vicente. If you completed the quest successfully you receive Cruelty's Heart that adds to willpower and strength, advancement, and the well key. If you failed, by killing Hides-His-Heart, Motierre, or you don't save Mortierre, you don't get anything except an angry vampire. Down to -71 instead of +80, so bring some charm with you...After this quest he offers the gift of vampirism, and you now go to Ocheeva for contracts.
The Lonely Wanderer you may do when you are already an Eliminator, but you may not so I'm including it here. You basically have to kill a high elf in the Imperial City and there's a short cut if you already know where and when to go. Bonus is to kill him securely, with no witnesses. The elf's name is Faelian, and Vicente will tell you that the elves are a tight knit group and one will know where Faelian is. The elf you talk to and get information from will tell you he lives in the Tiber Septim Hotel in the Talos Plaza District. Speak with Augusta Calidia to leave he lost all his money when he got addicted to skooma and his girlfriend Atraena lives in the hotel as well. If you find Faelian inside the hotel he will tell you to meet him later, thinking you're an addict too. Now you have two methods, if Atraena has a high disposition towards you she will tell you he visits Lorkmir's house during the day (from 11am to 5pm). It's abandoned, with the owner's body downstairs so he probably killed Lorkmir). The other way is to talk to Faelian outside of the hotel, if you have skooma you can give him some or get some from the supplier he tells you about. You can also pickpocket skooma off of him and give it to him (assuming he doesn't notice you). He then gives you the key for Lorkmir's house so no picking required. Shortcut: Go to Lormir's House in the Elven Gardens District between 11am and 5pm, pick the lock, and kill him inside. Return to Ocheeva for your gold and infamy point, and the well key and a promotion if you didn't get it last time. If you killed him in the secure location, you get the Shadowhunt bow that damages health and magicka.
Ah, finally, the chance to be a rank that fits your job in the way I've been describing it. To become an official Assassin you have yet another three quests to complete, Bad Medicine, Whodunit?, and Permanent Retirement. Just a heads up, I found all three of these quests a lot easier with an invisibility spell (that I think I got in the sanctuary) and Permanent Retirement was helpful with a chameleon spell to go with it (so I could use the bow without losing my invisibility and such).
Bad Medicine involves taking the medicine of a sick warlord and replacing it with a poison so nobody suspects the Dark Brotherhood. If you talk to your fellow guildmates they will tell you of an entrance nearby that is easier to get through since it isn't guarded. I went this way so I can't really tell you how to do the other way from my experience, but I made enough mistakes in the side entrance to advise this. The bonus is to not be detected, so avoid the guards or do one hit kills (they must be one hit without being detected). Sneak mode recommended, though I can't tell you what to do. There is one guard that will sit at the end of the water tunnels so grab the stuff from the chests and make your way quickly to the little hallway thing on your first left outside of the water. Life detect is helpful here as you may not see the guards, but they will see you. After you wait for that guard to pass into the path you just went into you should see a very dark curve and hear a conversation as you approach the two guards. Once they are done one will go towards you, just push yourself into the wall so they can pass and don't move. Since it's so dark they shouldn't see you, make your way through the shadows to the next hallway and you enter a large room. Again, follow the shadows and avoid the fire, go into the hallway and wait for the guard to pass to the cabinet area, hug the walls along the shadows until you are right near him and the cabinet. When he isn't facing the cabinet sneak up to it and switch the poison for the medicine and sneak back into the shadows. Make your way back to the hallway that enters into the room with the fire and take a left, sticking to the shadows. Don't go across the bridge thing, there's a guard on the other side, instead go to the end of the room where you will see a gate. Follow that wall without going through the gate and there's a couple doors, one being locked. Unlock it and you should be outside where you can escape back to Chedinhal and Ocheeva. If you got the bonus it is helpful in the next quest, The Deceiver's Finery is the item. It fortifies your speechcraft and personality (also useful for getting more money selling to the merchants).
Whodunit? is a quest that is one of my favorite party ideas, but in a more twisted way. Instead of one guest being murdered, or fake murdered if it's a party and not a real case, you must murder all of the party go-ers without them knowing it was you. That's actually the bonus, none of them knowing who it was. This is where the invisibility spell is helpful, just go invisible and kill. If you talk to your fellow brother and sisters, they will tell you that the bonus reward from the last quest would be helpful, if they trust you the guests are least likely to suspect you and thus, they won't attack you. If you make everyone hate you, you still get the bonus as long as you are undetected (the eye is invisible, not glowing) when you kill them. You can also kill them with a bow from a hidden area across the room, or give them poisoned apples, but Nels can't be killed this way. You can also Frenzy them and they will kill each other, but I just invisibility spelled and killed them that way. Remember any bribes can be recovered from their bodies, and there are many silver objects around that you can sell if you want (they aren't stolen). Here's some guests specifics if you can't get someone alone for some reason or you want a game plan before you start.
- Dovesi Dran- Talk to Primo about her and he will say he likes her, then if you go to her with a high enough disposition she will say she likes him to and will then go to his room (and be alone) so you can kill her. If you have already killed someone you can "say nothing" to her (the actual option, not avoiding talking to her) and she will go to the basement, sits on a stool facing the wall, and is an easy target. You can also get to her turn against some people near the end of it.
- Matilde Petit- If you talk to her about being an assassin she thinks it is a joke and later will offer to join you to look for the treasure together, goes off to the basement alone, and can be killed there. If only Dovesi is the only other person alive besides her she will attempt to kill Dovesi.
- Nels the Naughty- He likes to drink and usually sticks to the same area. If he is the only one left with Dovesi he will try to kill him if there is a weapon nearby (apparently nobody likes Dovesi, sad). Also if Matilde is the only one alive besides him he will try to attack her, but if hes the last alive he goes down to the basement.
- Neville- If he's the last one alive he puts on armor, but he only has one hit point so don't worry about not being able to kill him. If you do leave him last and you talk to him with a high disposition he will try to axe down the door (he is most weak here) but if his disposition is low he will suspect you and try to kill you. This won't effect your bonus as long as you are undetected.
- Primo Antonius- He sticks to the ground floor most of the time, but if he is the last one left along with Dovesi, Neville, Nels, or Matilde, he will attempt to kill the remaining guest if you have a high enough disposition with him.
Once all the guests are killed return to Ocheeva and get your gold. If you followed the limitations, the bonus is Night Mother's Blessing, a permanent increase of two to your Marksman, Security, Sneak, Acrobatics, and Blade skills.
Lastly, you have Permanent Retirement, a quest involving a retired guard that needs to be removed from existence. You have a bonus option of retrieving his finger and placing it into the desk of his successor in the Imperial CIty. All of the keys you will need for the bonus is on his body, along with his finger obviously, so go ahead and do this if you want. You also get an arrow that will kill him with one hit, but can't be used when he is wearing his armor. The location is Leyawiin and there is an area of water in the city that he goes swimming in (no armor of course). He does this every day between 3 and 8 pm, so make sure you are sneak and undetected (this is where i used chameleon as well as invisibility). Kill him with the arrow, one hit or you get a bounty even if undetected. Return now if you don't want the bonus, 500 gold, or keep reading. Take his finger and all the keys from his body and go to the Prison District of the Imperial City. At around 2:50 am there shouldn't be any guards in the office (late at night basically), but save just outside the door just in case. Right by the entrance is a desk, pick the lock and put the finger inside manually. The chest on the left of the desk has good treasures inside if you have the time or courage to get them, head outside undetected and return to the sanctuary for your 500 gold bonus and up to 600 leveled gold reward. The bodyguard who was watching Adamus will commit suicide, inside the City Barracks of Leyawiin you will find his body and a suicide note if you want some extra chuckles at your power.
Although this is an official rank in the game's system, you cannot actually achieve it and you skip right to Silencer. Too bad, yet less work? I have no idea, just read the next section.
I hope you didn't get too attached to your fellow sanctuary members (I kinda did, so oops on me) as this next quest will have you kill them all. Yes, that's right, kill them. Your brothers and sisters, something you aren't supposed to do in this guild, yet here you are. Anyway, it's called The Purification and comes from Lucien but good news, you don't have to kill that cute little rat Schemer. Since you have to kill M'raaj-Dar, I would advise buying items from him before you do this quest, the spells are available later but the items are unavailable. You also can't become a vampire after you do this quest (at least from Vicente, so don't fret, you can still get it).
A more specific guide follows this sentence. You get a letter from Lucien as your next contract from Ocheeva (you get a letter from Ocheeva but Lucien wrote it, just to avoid confusion over my odd wordings). Read it and learn that the Black Hand itself has a task for you and you cannot speak to anyone about it in the Sanctuary and head to Fort Farragut near Cheydinhal (this is where you get the poisoned apples for free). The letter warns you of residents in the fort but you can avoid them and enter through the hollowed out tree NW of the fort's tower, outside of the fort itself. When you find Lucien he tells you that the assassin among assassin you may have heard about is is definitely in the Cheydinhal Sanctuary so you must perform a Purification (a.k.a. killing all the members inside). You aren't a suspect since you are a new member, and he gives you a list of names to kill (not a literal list, he names them). He gives you some items to help you and you don't have to kill them all at once. You might want to use some techniques from the Whodunit? quest if you just picked them off one by one, if you are seen attacking a member of the sanctuary you will be attacked by everyone who saw it. Remember that Vicente is a vampire and so he is weak to garlic, put some in his pocket while he is sleeping (there are some in Antoinetta Marie's chest). Telaendril isn't in the sanctuary on Loredas and Sundas so you can either follow your marker, get the note from Ocheeva's corpse, or wait until Middas when she returns. Once everyone is dead though, return to Lucien, who tells you that you will be getting your contracts from letters now called Dead drops. Complete each contract to get the location of the dead drop and there is your reward and next contract. He also gives you his horse, Shadowmere (who is essential so you can't kill her, yay!).
The rank of Speaker requires many a quest, allow me to list them for you. They are: Affairs of a Wizard, Next of Kin, Broken Vows, Final Justice, A Matter of Honor, The Coldest Sleep, A Kiss Before Dying, and Following A Lead for a total of 8 quests. Do not worry as they are all fairly quick quests and won't even take all that long for me to explain, let alone do yourself.
Affairs of a Wizard is delivered at Hero Hill. You learn about your target, Celedaen. They are a necromancer in Leafrot Cave, inside there will be some leveled undead. Make sure you get the skill book, The Art of War Magic, as it raises destruction skills, then look for Celedaen's Journal. It tells of his quest to become a Worm Eremite and then tells that you can kill them if you remove their soul container when they are performing their transformation. Luckily, he is in the middle of his transformation so either pickpocket his Soul Container, Sands of Resolve, to kill him instantly, or battle him. The Soul Container looks like an hourglass. Once finished, you should go to Chorrol to complete the quest and get your next one.
Next of Kin involves killing an entire family. You only know the location of the first member, Perennia Draconis, the mother. She lives on a farm called Applewatch, near Bruma. If you talk to her and tell her you are looking for her children she will give you a list of their locations, or if you just kill her you can take it off of her corpse. She is tougher than she looks though, so be weary, and she has a dog to defend her. If you approach when shes sleeping she will go back to sleep after talking to you, making for an easy sneak attack. If she's sitting in her chair, make sure the dog isn't looking and sneak attack her, if you killed her in one hit and the dog didn't see you, he will walk over and howl over her body. From 6am-2pm she is outside, where she can be easily killed without alerting the dog (he stays inside). Matthias Draconis lives in the Imperial City, the Talos Plaza District. You have many options to kill him according to his schedule, in the evening he is in the Bloated Float so you can snipe him from a hidden area if your sneak is high enough. If you go to the basement of Umbacano Manor, he is a guard during the day so you can kill him with one blow sneaking or let him see you and wait for him to attack you, avoiding the bounty. Lastly, you can wait for him to be near a guard and cast a frenzy spell on him and he will attack the guards. Caelia Draconis is the next target, a captain of the guard in Leyawiin. Starting at 7:30 am she is alone in the Three Sisters Inn guarding some rooms, or you can find her patrolling the town and cast a frenzy near other guards. If you tell her you are going to kill her she will alert the guards and you will get a 1000 gold bounty (unless you run to the mages or fighters guild and they kill her). If you have a high enough Alchemy skill to make a couple good damage health poisons, you can wait for no guards to be nearby and tell her "Unfortunately, I need you dead." Then reduce her health enough that the poison will finish her off, you then get no bounty. To frenzy her, you should wait for her to be sleeping in the barracks as she will attack the guards Andreas Draconis is located in the Drunken Dragon Inn, Northeast of Leyawiin. If you tell him his mother bled like a pig or you want him dead he will attack you and you then can kill him without incurring a bounty. Otherwise you can cast a frenzy spell and he will attack the Imperial Guard, since you aren't the direct murderer you won't get a bounty. And finally, Sibylla Draconic is the last member to kill. She lives in Muck Valley Cavern, Southwest of Cheydinhal, that is filled with leveled natural predators. She will most likely be aggressive towards you unless you have a high fame, infamy, and personality. She doesn't have anything to say except normal rumor speak, so there's no point in trying to make her like you. If the battle is too tough, leave the cave, her animals won't follow her so it will be you and Shadowmere against her. She doesn't eat so poisoned apples won't work, she can't sleep either so she won't wear any enchanted items that drain health. Once all the family members are killed proceed to Skingrad Castle Courtyard for the next target and your reward.
Broken Vows tells you to kill J'Ghasta, a skilled boxer in Bruma. It tells you that he is expecting you and he has bribed the guards to ignore the fight if it goes into the street. He can be found in the secret training room in his basement, there's a hatch hidden near some rolls of cloth. If you have trouble finding it, switch to your local map in your menu. When you find him he will tell you to leave, any of the three responses he gives you will make him aggressive so be ready for a fight. Remember that I mentioned he is a boxer, so his unarmed attacks will deal some damage to your health and fatigue. You may want to wait for him to sleep between midnight and 5am, as that would be the only time you could sneak attack him. Before you leave, pick up the Black hand robe and hood from a locked keg on the lower floor and the two hand to hand skill books on a desk in the basement. They are called, Ahzirr Traajijazeri and Immortal Blood, and are located on the bottom shelf of the bookshelf on the upper floor. After you do those you should head to the Old Bridge, South of the Imperial City, where you will find your next drop below it and your payment.
Final Justice is possibly going to be difficult for you as the target is carrying a powerful enchanted sword. Her name is Shaleez, and she is a psychopathic killer so she is used to killing people and will attack on sight. She is in the Flooded Mine North of Bravil, although it is flooded you won't need a water breathing ability as there are plenty of air pockets but get it if you feel the need. She has one non-enchanted shortsword, an enchanted shortsword, and an enchanted longsword (unless you do the quest at level 1 or 2 then she doesn't have the enchanted weapons). It is also underwater fighting, which is more difficult than normal fighting. Once you kill her you should head to Fort Redman, North of Leyawiin, and get your contract from the coffin just outside the ruins.
A Matter of Honor involves killing a Dunmer merchant, by the name of Alval Uvani. You may recognize this name from my list of targets to join the guild, but most likely you haven't killed him yet so let me explain what to do. He is in Bravil, at the Lonely Suitor Lodge on Morndas to Tirdas, Skingrad at the West Weald Inn from Middas to Turdas, Bruma at Olav's Tap and Tack on Fredas to Loredas, and his house in Leyawiin on Sundas. You can also find him on the roads between the towns between the days listed. If you want to kill him in one of the Inns or his house, put some mead in front of him, he's allergic to honey. Replace all the vendor's food with mead or his own food with it for the same effect. He is also in the wilderness a lot and so he may have been killed by a wild animal or something, the quest will automatically update and you will be told to go to the next spot. The next dead drop is in the Market District, in a hollowed-out tree stump behind Stonewall Shields.
The Coldest Sleep involves traveling to Knoll Mountain, near Bruma. There you must kill Havilstein Hoar-Blood, and his wolf companion. If you go from the East Gate of Brumae you take the left path when you get to the crossroads, then the first right when you get to Dragonclaw Rock, there is a bandit camp, and the Mountain is just past the camp across a bridge. He is well equipped with leveled light armor, a leveled battleaxe that is usually enchanted, and his wolf companion to help him. He doesn't eat so you can't use poisoned apples, but he sleeps so you can sneak attack him. If you're still having trouble try to use the steep mountains to your advantage and have him fall to his death. Once he's dead you should head to Nornal, ruins filled with rats, crab,s and marauders. Head down the stairs and take a right dive under the water and swim towards the door. You can pick the lock, water walk across the iron bars, or jump out of the water and over the gate if you don't have the key. (Located in Chest in Nornal Ageasel, Chest in Leyawiin Mages Guild 2nd Floor West.)
A Kiss Before Dying if your ready for the second to last drop quest then read on. You have to kill a Wood Elf named Ungolim in Bravil. You may have seen him looking at the statue of the Lucky Lady every night between 5pm and 1am. He bribed the guards so they won't help either of you if the fight is outside. He is in his house during the day but you can only go in with a key that you would have to pickpocket off of him before you start this quest. Otherwise, if you go outside in Bravil during the night he will attack you on sight with his bow. Although the guards won't attack, if you sidestep behind one of them when he shoots an arrow they will attack him if it hits. If you are worried about a bounty, since he attacks you first then you shouldn't get one. Don't do it on a rooftop though or anywhere else where you can't easily walk to you as Lucien will come to talk to you after you kill Ungolim.
Following A Lead starts off with a furious Lucien saying you betrayed the guild and you must die for it. If you noticed, the last few letters have been in a different handwriting and this is what he's talking about. He tells you that you have been killing other members of t he black hand as a part of the plot of the real traitor. He tells you to go to Anvil, at the sight of the next dead drop to find out who they are. Wait in sneak mode behind the barrel until Enilroth puts the Dead Drop orders in the barrel and you get a journal entry. Confront him and he swears he isn't the traitor and he was just paid to put the drops there. He tells you that the traitor is staying in the lighthouse under mysterious circumstances. He has the 500 gold reward on him so kill or steal it from him. Get the key from the lighthouse keeper from whatever means you feel necessary and then head to the cellar door. Once down in the cellar you find various dead animals and people strewn about, even a severed head called "mother's head".Find the locked door, on the other side is a Crazed Dog that you can kill or sneak around to find the Traitor's Diary. They are a member of the Brotherhood since childhood waiting for the moment to strike against the group after Lucien killed his mother. The diary also mentioned killing the crew of the Serpent's Wake, a side quest in Anvil involves killing the spirits on that ship. Now you have to go back to Applewatch Farm to meet with Lucien but you find that they murdered him, believing he was the traitor. Arquen will approach you and tell you that the traitor has been dealth with, that you are now the speaker in Lucien's place, and that you should speak with him again between midnight and 3am to leave for the sanctuary (ask about the night mother).
This rank, called Listener in case you missed it, only requires one quest to do. Unlike the last rank which may have had you a little frustrated if you had no idea when it would end, and it is called Honor Thy Mother (the Night Mother, perhaps?). I will also explain the quest you receive after this as I don't think it should require its own section, its name is Whispers of Death.
Honor Thy Mother starts as soon as you talk to Arquen and he transports you to Bravil. Bring as little as you can physically hold while still fight effectively before you enter the sanctuary probably before you even start this quest. You enter the hidden sanctuary of the Night Mother that is entered through the Lucky Old Lady statue. Once they summon the Night Mother, the traitor reveals himself and kill Belisarius and Banus, then try to attack the Night Mother herself. You are then free to help Arquen kill Mathiew Bellamont, the traitor. The Night Mother then tells you that she knew all about what happened and that he was the traitor, and you become to the new listener for the guild. You now must take orders from the Night Mother and relay them to the speakers. (I say have to but you don't really have to, there is no consequence for not doing it.) She then powers up your Blade of Woe to finally become an enchanted weapon, and allows you to retrieve anything in her tomb. Take all that you want as you won't be able to come back again after you leave. You can also drop everything in front of the night mother, pick it all up and then talk to her, she will transport you to the sanctuary and you can drop it there. IF you save before you enter the trapdoor you can try for better loot. There also is a rare alchemy ingredient, lichor, in front of the large sarcophagus. You are now finished with the Dark Brotherhood quests, but there is one you can do every week for 200 gold.
Whispers of Death is a pretty simple quest, just go to the Lucky Old Lady statue as if you were getting her blessing and the Night Mother will tell you information to tell your speaker. You will get one of the people and a location but none are in Cyrodiil so you can't do it yourself, so instead go to Arquen in the Cheydinhal Sanctuary and it will be taken care of and you get your earnings for the previous week. This quest is never completed so don't expect it to ever get an update.