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Introduction - The Thieves Guild
Note that Oblivion’s guild system is not restricted. The best warriors and mages will probably want to go ahead and join the Thieves Guild for its incredible benefits. Thieves will also find this to be a vital quest, since they will only be able to fence stolen items through Thieves Guild merchants and fences. Warriors and mages will also come across “stolen" items during their travels. Since a large number of the best items end up counting as stolen, it’s nice to be able to quickly fence it and buy it back to “clean" the item.
Even if you’re not a thief character, stealing is one of the quickest ways to safely earn cash and it can usually be done without any real skill. If you can watch for guards and not awaken sleeping owners, then you’re set for a lot of money. This is also true for most of the special Thieves Guild missions. You don't necessarily need to have many points in sneak. Just strip off your armor and move around the guards.
In order to get the quest “Joining the Thieves Guild" you will need to gain the attention of the Thieves Guild and learn about their test.
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Finding out About the Thieves Guild
The easiest way to do this is to look at a wanted posted that’s on the walls of the Imperial City. This will add “Gray Fox" as a conversation topic. Using either Speechcraft, a Charm spell or bribery, get the disposition of a beggar up and ask them about the Gray Fox. They’ll point you to the meeting.
If you’re arrested for stealing at any point, then you’ll receive a note telling you that your skills could be put to much better use inside the Thieves Guild.
Apparently, just getting the basics about the Gray Fox is enough, since that will trigger the meeting. Bribing Armand will convince him to let you try.
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May the Best Thief Win - Amantius Allectus
Regardless of how you learn of the Thieves Guild entrance exam, head over to the Waterfront district and enter the Garden of Dareloth at around midnight (wait if you have to do so). It’s just a little corner past a few beggars’ bedrolls behind an abandoned house. Armand Christophe is the Imperial City Doyen and the man that we have to impress to enter the Thieves Guild. He also holds a bright torch, so he’s easy to find. You may have to boost his disposition a bit to get him to tell you about the test, although mentioning the beggar’s approval (through the “Gray Fox" option) should help.
Regardless, he’ll explain the unique test for the unique circumstance. Since there are three potential recruits, he’s requiring a competition. This is a little tricky.
Standard theft rules apply. You can’t kill anyone involved in the quest while it’s active. Other than that, it’s pretty much your call. Remember that you aren’t in the Thieves Guild yet, so their more strict rules don’t apply.
The diary belongs to Amantius Allectus. He’s an alchemist who lives in the Temple District of Imperial City. You can get a marker for his house by asking any beggar about him and paying 5 coins. There's one sleeping on the bedroom by the wall right outside the Garden of Dareloth.
Note that, yes, Amusei is an idiot. He’ll just wander around the Elven Gardens and the rest of the city aimlessly while looking for the house. He’ll still be at it the next day.
Methredhel, on the other hand, is a genius thief. She already knows where Amantius Allectus lives and she’ll sprint to his house to grab the diary. It may not actually be possible to beat her. If you’re not built as a thief, then don’t worry. We have several other options. If you want to try, then you can try to outrun her. It will be hard for a new character though since she is really fast.
Fast travel can even the game, since I believe you’ll both move at the “default" speed and end up in the Temple District at the same time. You may be able to cut a corner and beat Methredhel there. If she makes it there before you, then you might still be able to beat her. She has to sneak around the house briefly before she figures out that it’s in the desk by the door. If you can grab it first, then congratulations. On midnight tomorrow you can turn it back in with Armand to gain access to the first fence and join the Thieves Guild.
If you didn't get Amantius Allectus' Diary, then just read more on the next page for you new options.
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May the Best Thief Win - Methredhel Has The Diary
Remember that you aren’t in the Thieves Guild. You can still cause trouble in the Waterfront and steal from other thieves with no real consequences. Praise the mighty loophole in the rules and talk to a beggar. They should be able to mark Methredhel’s house on your map for 5 coins. It’s not really hard to find though, considering the size of the Waterfront.
Methredhel always sleeps in (like the beggars will all say), but today she’ll pretty much sleep until she leaves for dinner at six. At any point in the day, just wait outside her door until the people in the Waterfront aren’t around. Just wait in one hour increments if you can’t catch much of a break. Pick the lock and go inside. Her roommate might be there, which isn’t a disaster. Just leave and wait again until you see the roommate leave, then try again. Methredhel hid Amantius Allectus’ diary in “Methredhel’s Chest" in the corner. Pick the lock and steal the diary.
If you just can’t pull this off either, then wait until Methredhel leaves the house to deliver the diary at midnight. You can also just wait by the Garden. Save and pickpocket her until you get it (reload if you fail). It’s okay if you’re “seen" since a successful pickpocket isn’t seen as a crime. It’s just harder to pull off successfully.
If you manage to steal Amantius Allectus’ diary from Methredhel at any point, you can turn it in normally to learn that Armand takes our side. A loophole is a loophole and we showed a lot of initiative and creativity. That’s what you call "management potential."
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Joining the Thieves Guild - Another Option
I f you just can’t or won’t steal Amantius Allectus’ diary from Methredhel, then you can take a second solo test. This one is ridiculously easy for any thief. You just have to steal a marked sword, “Rohassan’s Antique Cutlass" from her bedroom above “A Fighting Chance." It’s actually pretty easy and robbing a merchant’s bedroom is a vital skill for a thief.
The only difficult note is that her bedroom is guarded by a dog. You can kill the dog with no penalty (it's officially a creature), but you’ll need to do it quietly for a night robbery. Otherwise you’ll wake up Rohassan and fail. If you have a spell to Command or Calm animals, then you can use it. You might also be able to just sneak around the dog if you have some good Chameleon or Invisibility spells.
The easiest option is just a daytime robbery though. Every thief should know how to do this, since it's a useful skill for petty theft during daylight hours. Use the stairs for cover and crouch by their bedroom door. If you just run up there normally, you won’t freak out the owner if you're not sneaking around their store. Crouch at the top and make sure that they can’t see you. Pick the door and go inside. You can kill the dog with no one around to notice and grab the cutlass from the chest. Take it back and turn it in at the next meeting to gain access to the Thieves Guild.