Permanent Retirement - Killing Adamus Phillida
This is a quick one if you know what you’re doing. You need to assassinate an Imperial Guard Captain, Adamus Phillida. He just retired to Leyawiin. Unfortunately, he always wears thick guard armor and he has a personal bodyguard at his side for most of the day. We are allowed the use of the special Rose of Sithis for this mission though. Just hitting any unarmored portion of his body with this arrow will guarantee a kill. The bonus is basically a separate mission, so we’ll handle the finger delivery in a minute.
There are only a few real times to hit and one “proper" way to do it.
Rose of Sithis - The proper way is to follow him around in the early afternoon. He’ll walk up to a pond close to the castle at some point. You should be able to crouch at some point by the pond. There are several small alleys on the sides and a number of nice rocks. Just wait in one place for a moment and they should forget about you.
Use any bow and the Rose of Sithis and just wait. He takes his armor off to swim, so you just have to hit any part of him. Save before you take the shot and then get ready to run.
Barracks - If you can manage to sneak past his bodyguard on duty by the stairs (you’ll need Chamleon or Invisibilty), you can walk up to the bed where he’s sleeping and fire the Rose of Sithis into his face.
Ambush - You don’t have to kill him with the Rose of Sithis. He should occasionally walk out of the city to the Coast Guard Station. You can just attack Adamus Phillida and his bodyguard, if you can safely overpower them. This will probably get messy and result in a big bounty though.
There’s a rather unfortunate problem with the quest “Permanent Retirement." Adamus Phillida can be killed with the Rose of Sithis from cover, and you’ll still get a 40 gold bounty for the assault. This is just because of the way that it works. The Rose of Sithis does arrow damage and then applies the poison. Adamus responds to the arrow damage and places a bounty on your head for assault, and he then dies from the poison. It’s possible to use an invisibility potion right after you fire the arrow to avoid detection, but the cost of the potion is higher than the bounty, so that seems a little pointless.
Worse, even if you are in no way responsible for the kill (if you manage to pull off a 0 bounty kill), his bodyguard will still attack you. This makes other allied guards join in. If you fight back, then you’ll rack up a lot of bounties. Try to yield. I had success with his bodyguard once. If you get a bounty from killing Adamus Phillida, you have two options. The first is to yield to a guard and surrender. Pay the 40 gold fine or spend a night in jail. You can just rob the evidence chest in the castle jail to get your stuff back.
You can also run if you’re in the Thieves Guild. The guards won’t follow you far out of the city, especially if you get into the water. Once you put a little distance between the two of you, fast travel to the Waterfront and talk to Armand Christophe to only pay 20 gold. You also need to be in Imperial City for the bonus, so it’s not a big deal.