Oblivion:Permanent Retirement

Quick Walkthrough
# Receive the contract and the arrow for the assassination.
# Eliminate Adamus Phillida.
# (Optional) Take his finger and place it in the desk.
# Return to Ocheeva to collect your reward.

Detailed Walkthrough
The Assassin's Gambit
The mini-quest to get your next contract from Ocheeva is named "The Assassin's Gambit". She tells you that you must kill Adamus Phillida, a recently retired Imperial Legion officer, who has taken up residence in the City Watch barracks in Leyawiin. For this task, you have been given an enchanted arrow called the Rose of Sithis. The Rose of Sithis is specially commissioned and crafted to kill one person--in this case, Adamus Phillida. When fired on anyone else, it only wounds them. If you can hit Phillida with the arrow when he is not wearing his armor, the strike will be fatal. Head to Leyawiin, stalk Adamus Phillida, and attack when the moment is right. The contract will be complete when Phillida is dead, whether you use the Rose of Sithis or not. When Adamus Phillida is dead, you can return to the Sanctuary for your reward. If you want to receive your bonus, however, there is one more task you must complete. Phillida wears an Imperial Legion ring. Take his finger, with the ring still attached, and put it in the desk of Phillida's Imperial Legion successor, in his office in the Imperial City.

Making the Kill
After you receive the quest from Ocheeva, travel to Leyawiin and head to the small pond. Every day at around 3-8pm, Adamus, accompanied by his bodyguard, will unequip his armor and take a swim in the pond. Wait for him to go into the water, then go into sneak mode and make sure you are not detected. Find a good spot, and shoot the Rose of Sithis at a part of his body that is sticking out of the water. You can also kill him using the Rose of Sithis while he's sleeping in the barracks, as he is unarmored then, as well. He will die instantly (even though it only counts as assault) and you can return to the sanctuary for your reward.

It is very hard to avoid incurring a bounty from this kill, as there is a glitch that will get you 40 bounty even if you shoot him with the Rose undetected. You must kill him in one hit by any means to avoid a bounty.

If you really want a challenge, one possible approach is to walk up to Adamus Phillida and inform him to his face what you're there for. This will result in every single guard in the city attempting to kill you. If this doesn't end with your death, it will probably end in a massive bounty. You should not do this unless you're high level and a member of the Thieves Guild.

Loot the Finger
Now, loot the finger from his body (along with a bunch of keys to various places) and head for Imperial City. Now enter the Prison District of the Imperial City, and wait for nightfall; just before 3am. There should be no guards in the office. Go into Sneak mode, and enter the Imperial Legion Offices (remember all the keys?). As previously mentioned, there shouldn't be any guards around so late at night, so head to the desk right by the entrance and pick the lock. Place the finger in the desk (by clicking on the desk and, within the inventory window, clicking on the finger; unlike some other quests, the quest item does not automatically get transferred for you). The chest to the left of the desk is known to have good treasures in it, it would be a good idea to loot it while you are there. Head outside undetected, then head to the sanctuary for your reward and bonus.

The reward for this quest is the standard 50-600 gold (level-dependent) reward given for each Dark Brotherhood quest. The bonus is an additional 500 gold.

Notes
Be sure to use the key from Adamus's body on the Commanders Chest to the left of the desk, it contains a level dependent amount of gold and some random armor.
After you complete this quest, a special edition of the Black Horse Courier is published: Adamus Phillida Slain!.
After you complete this quest, Adamus Phillida's bodyguard will commit suicide. The next time you return to the city you can find his corpse if you visit the Leyawiin City Watch Barracks. On his body is a suicide note explaining the reason behind his untimely demise:
:''"This was my big break! Finally I'm given something important to do, and what happens? I blow it! All I had to do was keep Phillida alive! That's it! But no! I couldn't even accomplish that! Father was right -- I'm an idiot, and I haven't amounted to anything! I let everyone down, so this is it. Goodbye cruel Empire! I'm ending it all!"''
It seems this quest originally had a different plot, or at least, extra elements to the existing plot. An NPC named Gwendolyn and two Imperial Legion Centurions (with ID names "Ceremony", suggesting a funeral for Adamus Phillida) are defined in the Construction Set with ids that start with "Dark09", suggesting they were intended to play roles in this quest. None of them exist in the game, however.
If you used the Rose to kill Phillida, it's possible to find it in his corpse. Taking it has no consequences, and it can still be used as a regular arrow.

Bugs
 
 
 
 
 
 
This can be fixed by casting an area Charm spell on the bodyguard and any other city guards helping him and then yielding to them. Since you do not have a bounty on your head, all guards including the bodyguard will immediately turn peaceful and walk away.
 
Loading another save game can get you out of arrest with no problems.

Journal Entries