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Head to Applewatch and speak to her, extract the location of her children, and then kill her. The best way to do this is to pretend to be the shopping service she has hired to send gifts to all her kids. She'll provide a list of all the other Draconis family members as well as 100 for the errand. Kill her and then move on.
If she is killed without being asked about the children, the list can still be found on her body. If she isn't killed in one go, she will run out of the cottage and run fast and it can be hard to keep up with her. Not only is it difficult to catch her, one of the possible roads she may run on will pass an Imperial Guard, who she will call for help. This adds a bounty, and the Imperial Guard to deal with.
Caelia is a city watch guard in Leyawiin who works a night shift. She is constantly armed and armored, making her difficult to take down in one strike. Because of this, there are several possible methods to kill her without earning a large bounty or provoking the other Leyawiin guards.
Caelia finishes her watch at 7 am. She will then go to a private room upstairs in the Three Sisters Inn, where she will be alone. This is the ideal time to attack her, as it is the only time there are no other guards in the area.
At any point, the Hero can talk to her and taunt her by saying that they need her dead, causing her to attack. Killing her at this point should be considered self-defense, and will not incur a bounty. If the Hero is not strong enough to kill her alone, there are a number of ways to get others to kill her:
- Lure her to any place where the Hero has high disposition with the characters there, such as the Leyawiin Mages Guild or Blackwood Company Hall. Friendly NPCs will attack and overwhelm her, leaving them with no bounty. Note that Blackwood Company members are essential before the Fighters Guild questline is completed, so Caelia cannot kill them.
- If the nearby Oblivion Gate is open, she can be led there and into the lava, where she will quickly die.
- There is a chandelier in the Three Sisters Inn that the Hero may be able to jump to. From here, they can summon creatures to attack Caelia, but she will be unable to reach them.
- While she is asleep, she can be reverse-pickpocketed with a cursed item. When provoked, she will take damage every time she attacks the Hero, who only has to survive the assault long enough for her to kill herself.
- Using a sufficiently high-level Frenzy spell will also cause Caelia to attack nearby characters and the Hero, and they will not be blamed for killing her in self-defense. This has the advantage of being usable anywhere, such as in the guard barracks.
- If the Hero doesn't mind getting a small bounty, they can attack her at any time and whittle her health down with normal attacks, then use a poison attack with a long duration. If she dies from the poison, the Hero will only receive a 40 bounty for assault.
- Conjurers can use Summon Dremora (ideal for their higher level), then attack the summoned creature three times. This will make it hostile, and it will attack the Hero and anyone nearby. If Caelia is there, she will attempt to help them and fight the creature. Avoid the Dremora to allow Caelia to get its attention. One can then summon more Dremora and frenzy all of them, eventually overwhelming Caelia. This will incur no bounty. Note that other guards in the area will also come to help, so this method is best used when Caelia is alone.
- If the Hero attacks Caelia before summoning creatures, they will receive a 1000 bounty if any of the creatures kills Caelia, even if they were frenzied.
- While wearing the Gray Cowl of Nocturnal, no crimes the Hero commits will be attributed to them. Kill her while wearing the Cowl, then remove it afterward.
- Note that Chokeberries or poisoned apples cannot be used to kill her, as she has a respawning source of food in her possession.
- While fighting her in the Three Sister's Inn, it is possible to get the sisters who run the inn to attack and kill Caelia.
Andreas is located at The Drunken Dragon Inn. There is a guard always posted in his room facing him most times (on some VERY RARE occasions he will turn away allowing the Hero to sneak up on Andreas). This makes it very difficult to kill him directly. However, there are several ways to trick him into attacking the Hero, allowing them to kill him in self-defense:
- The Hero can talk to him and say either that his mother bled like a pig, or that they would like to kill him. When he attacks, the guard will also attack and help kill him.
- A high-level Frenzy spell has the same effect.
- Note that the same strategies apply here as applied with Caelia; for example, leading Andreas to a group of friendly NPCs while hostile will cause them to attack him.
It is possible to kill him directly. When he's asleep, the Hero can hide from the guard behind the counter, and can use a sneak attack to kill Andreas. They can also hide on the steps behind the guard and use a bow to attack (a poison with Paralyze and/or Damage Health effects can help non-archers, while still preserving their stealth).
Sibylla lives in Muck Valley Cavern with her surrogate family of wild animals. Killing her carries no risk of a bounty, so only standard dungeon-crawling and boss strategies are necessary. The cavern consists of 3 zones, with Sibylla in the final zone. However, it's also possible that the Hero will encounter Sibylla facing away from them as soon as they enter the cavern.
The final family member can be found in the Talos Plaza District of the Imperial City. Matthias works as a guard in Umbacano Manor, where he can be found in the basement. Like his siblings, he can be goaded into attacking the Hero through conversation, and the other guard nearby will attempt to kill him.
When he leaves the manor, he will eventually enter a stonewalled garden. He will be isolated here, making it a good place to attack him.
Matthias sleeps upstairs in his house from 12 am - 5 am. If the Hero can defeat the lock on the door, this is the ideal time to kill him. This task is further complicated by Collatinus Vedius, who also lives in the house. Having a high sneak score, and certain spells (such as Invisibility or Chameleon) will make the infiltration easier.
When the entire family lies dead, the Hero can pick up their reward and new orders at the next dead drop in Skingrad Castle courtyard, inside the well.
I have received my new orders from Lucien Lachance. I must kill every member of the Draconis family -- Perennia Draconis, Matthias Draconis, Andreas Draconis, Sibylla Draconis and Caelia Draconis. I know the location of only the family matron, Perennia Draconis, who can be found on the farm known as Applewatch. I should head to Applewatch, find out as much information as I can on the locations of the other family members, and then systematically kill them all.
Perennia Draconis has given me a document that lists the locations of all the members of her family. She thought I was the delivery person she hired to buy gifts for her children. I will instead use the list to find and slay each family member. I should start with Perennia herself. Then I must kill Matthias Draconis in the Talos Plaza District of the Imperial City, Andreas Draconis in the Drunken Dragon Inn, Sibylla Draconis in Muck Valley Cavern and Caelia Draconis in Castle Leyawiin.
Every member of the Draconis family has been killed. I must pick up my reward and next contract at the dead drop located in the stone well in the Castle Skingrad Courtyard.
- Andreas Draconis of the Drunken Dragon Inn suggests that the Hero go to the Inn of Ill Omen or the Tiber Septim Hotel instead. Both of those inns are involved with a Dark Brotherhood quest.
- Killing Matthias while the Ahdarji's Heirloom quest is active will result in expulsion from the Thieves Guild, and the Hero must pay the blood price to rejoin.
- If the Hero returns to Applewatch sometime after completing the quest, tombstones for all five Draconis members can be found, with a personalized epitaph for each, and Caelia's sword leaning against hers. Perennia's headstone reads, "Here lies Perennia Draconis -- May her spirit forever curse the murderer who stole her precious life." Reading it causes her ghost to spawn directly behind the Hero and attack.
- If any Draconis family members are killed before the quest begins, their part of the quest will be considered successful as soon as the quest is acquired.