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The Elder Scrolls IV: Oblivion Hints
Legion Commander's Chest
1 of 11: This chest can be found on the floor to the left of the Legion Commander's desk in the Imperial Legion Offices in the Prison District.
2 of 11: It contains lots of random, leveled loot, so it's good to raid it frequently, especially after you reach a fairly high level.
3 of 11: The only problem is that the office doors are locked, and it's a crime to be seen picking them open or moving around inside.
4 of 11: The keys to the chest and one office door are in the possession of Adamus Phillida, who can usually be found inside the offices or wandering around the Prison or Market Districts.
5 of 11: NOTE: After you reach a certain point in the Dark Brotherhood questline, Phillida will retire to Leyawiin. Since you're sent to kill him, you won't have to pickpocket the keys from him if you wait until you're doing that quest in order to get them.
6 of 11: After you get the keys from Phillida, there's still the matter of moving through the offices unseen.
7 of 11: Going in through the right office door (the one that leads directly to the room with the Legion Commander's desk) will ensure that you're seen if anyone is sitting at the desk or standing anywhere near it.
8 of 11: Unless someone's in the adjacent mess hall room, it's easier to sneak through it to the door that connects it to the Legion Commander's area.
9 of 11: Even if someone is sitting at the desk, you should be able to open the Legion Commander's chest and claim the loot from it unseen. If not, practice up your Sneak skill and try again.
10 of 11: And don't forget that the chest respawns every few days. Keep coming back for more!
11 of 11: TIP: Quicksave right before you enter the Imperial Legion Offices. Not only will you want to quickrestore and try again if you get caught, but you'll also want to try again if you don't like what you get from the chest.