Adamus Phillida (whom you may recall from "The Lonely Wanderer") is retiring. After having made life miserable for the Dark Brotherhood, you are to ensure that his retirement is short and, if possible, send a message to his successor. In order to accomplish this, the Black Hand has authorized the use of the "Rose of Sithis". This is a special enchanted arrow that will instantly slay its intended victim. The only problem is that it will not penetrate armor. So your problem has several components to it. First you must kill Phillida. Second, you should do it at a time when he is not wearing his armor. Third, you should do it with the Rose of Sithis. Fourth, you need to retrieve his finger with his Legion Signet Ring and put it in the desk of the Legion Commander in the Prison district of the Imperial City as a warning to leave the Dark Brotherhood alone. And you should do all of this without getting caught (unless you feel like coughing up some serious golds for bounties).
Once again, Teinaava has a useful observation. The only time he takes off his armor is to sleep and to swim.
So off to Leyawiin you go. Phillida sleeps in the barracks, so offing him there is going to be quite a problem. But he goes for a swim every afternoon at about 3, so he'll be out in the open, more or less alone, and unarmored. Sounds perfect.
Almost. There have been times when I have been able to shoot him with absolutely no repercussions and times when I end up with a 1000 gold bounty and still other times when the whole city guard came crashing down on my head. As best as I can tell, it seems to depend upon how far away from his bodyguard he gets before shooting (not to mention the problem of wandering NPCs who might see). So stealth yourself, equip your bow and the Rose of Sithis and wait for him to get as far away from the stairs as possible. If your stealth meter isn't lit, you should be good to go.
Collect his finger (and a pile of really useful keys), check your bounty and head for someplace other than Leyawiin. If you have a bounty and are in the Thieves Guild, you'll want to travel to the Imperial City Waterfront and get Armand Christophe to pay off your fines. If you're not, you'll want to find a guard somewhere and get that cleared up or you're partially hosed for the next phase of the mission.
Go the the Imperial Prison (you'll definitely be clearing up that bounty if you haven't taken care of it by now). Go left and you'll see two doors. The left door leads into the kitchens and has a "Very Easy" lock. The right door leads into the Imperial Legion Commander's Office and has a "Very Hard" lock. Even though you have a key for it, you do not want to go into the commander's office. Reason number one is that there is almost always someone in there, so you're automatically busted for trespassing. Reason number two is that the guards care a lot more about someone breaking into the commander's office than they do about someone breaking into the kitchen, so it's a little easier to escape detection that way.
The commander's office connects to the kitchens through a locked door, but the two are in the same area. A nice little "Detect Life" spell or effect will let you know when the coast is clear (usually between 2 and 5 in the morning), so you can go in that way. Activate the desk to deposit the finger and then go out the way you came.
Report back to Ocheeva to collect your fee. If you managed to deposit the finger in the commander's desk, there's an extra 500 golds in it for you.
This is the last contract from Ocheeva, so make your farewells. If you'd like to become a Vampire, now would be a good time to talk to Vicente Valtiere about it.