To start the Thieves Guild questline in The Elder Scrolls IV: Oblivion, you need to first discover the location of the guild's initiation meeting and then attend it at midnight. Here are the main methods to begin:
- Get caught stealing and serve jail time: Commit a theft or minor crime, get arrested, and serve your sentence in jail. After release, wait or explore the Imperial City until you are approached by a follower of the Gray Fox who gives you a note inviting you to a meeting in the Garden of Dareloth in the Waterfront District at midnight
- Raise a beggar's disposition: Find a beggar in the Imperial City and increase their disposition until they like you enough. Then talk to them about the Gray Fox, and they will reveal the location of the guild and instruct you to go to the Garden of Dareloth at midnight
- Go directly to the Garden of Dareloth: If you already know the location, you can simply show up at the Garden of Dareloth in the Waterfront District at midnight without prior knowledge, and the initiation event will start
At the meeting, you will talk to Armand Christophe, who will give you a trial quest called "May the Best Thief Win." This involves stealing a diary from Amantius Allectus' house in the Temple District without killing him. Successfully completing this quest officially grants you membership in the Thieves Guild
. In summary, the quickest way is to get caught stealing and serve jail time, then attend the midnight meeting at the Garden of Dareloth. Alternatively, raising a beggar's disposition or going directly to the meeting location also works to start your journey in the Thieves Guild
