- Quest Giver: Ocheeva in Cheydinhal
- Previous Quest: Whodunit?
- Next Quest: The Purification
- Reward: Up to 600 gold(depending on level), bonus of 500 more. Promotion to the rank of Assassin
- Fame/Infamy Change: Infamy +1
- Quest ID: Dark09Retirement
 The Assassin's Gambit
Go to Ocheeva for your next contract. Adamus Phillida has retired from his Imperial Legion career and is taking it easy in Leyawiin. Because of the captain's past relations with the Dark Brotherhood Sithis is not content to let him rest. You are to take his life, and to this end you have been given the Rose of Sithis, an enchanted arrow capable of killing him in one blow so long as he is unarmored. You may kill him any way you like, the arrow is just for drama and convenience. You may return to Ocheeva for your reward after he is dead. To receive the bonus you need to take the finger bearing his signet ring from his body and place it in the desk of his successor in the Imperial Legion offices located in the Imperial City's Prison District.
 Permanent Retirement
Travel to Leyawiin and find Phillida. He and his bodyguard walk a circuit through the town and end in the coast guard station right outside of the northern gate. Late in the evening, around sunset, Phillida removes his armor and swims in a body of water near the poorer-looking houses of Leyawiin. This is you best chance to kill him with or without the Rose. Even if you kill him undetected you may still get a bounty for assault, not murder, and guards will attempt to arrest you. After he is dead you may return for your reward.
- You can avoid the bounty if you reverse-pickpocket a poisoned apple into his inventory kill him that way. M'raaj-Dar has some for sale at the Sanctuary.
- If you have the Gray Cowl of Nocturnal from the Thieves Guild quest line you can use the cowl to avoid a bounty on your own head.
- Reverse-pickpocketing an article of clothing with a self-destructive enchantment for him to wear. It may take a long time depending on the enchantment but he will eventually die. Equip the Gray Cowl of Nocturnal and hide inside an empty building such as the player's house if you own it and unequip it after you get the message that he is dead.
 Job Insecurity
If you want the bonus take Phillida's finger and keys and head to the offices of the Imperial Legion. Wait until nighttime and enter sneak mode. At about midnight a guard inside will retire for the evening leaving the the desk and Legion commander's chest unguarded. Open the desk and deposit the finger. One of the keys you took from Phillida will open the chest on the opposite side of the desk and it contains some good loot, take it. Head back to Ocheeva.
For killing Phillida the reward is leveled gold to a maximum of 600. The bonus is 500 more, no useful items or attribute/skill buffs this time.