While there are other secretive factions in Oblivion: Remastered, the Thieves Guild is one of the most challenging to join, or at least more time-consuming. Instead of killing someone or walking into a hall, you’ll need to gather information, bribe people, persuade a few, befriend some, and then you’ll finally be able to join this organization. Since it is a daunting task, we’ve prepared a quick guide to help you join the best Thieves in Cyrodiil.
Joining the Thieves Guild in Oblivion: Remastered

In truth, there are three ways to join the Thieves Guild in Oblivion: Remastered. However, we’ll focus on the easiest one, or at least the most straightforward one.
- Head to the Imperial City.
- Walk around the city until you find a Gray Fox poster.
- After interacting with the poster, you’ll get a new dialogue option with some NPCs. It is recommended to speak with a Guard until the option appears, and keep choosing that option until you get information about Waterfront.
- Head to the Waterfront District. You’ll need to increase your disposition with some beggars around the area. The best one for this is Puny Ancus.
- If you’re having trouble increasing your disposition by talking, bribe them. That will raise your disposition even further. You need 80 disposition to progress the quest.
- Once you reach that disposition level, you’ll unlock an option that will let you “work with Gray Fox.” Choose it and head to the meeting at midnight.
- After that, speak with Armand Christophe to join the guild.
Note: You can skip most of the steps by simply interacting with the poster and then heading to the meeting point at midnight, located in the Garden of Daleroth. You’ll still need to raise your disposition with Armand to 60, though.
In case you don’t want to follow the above route, you can either get arrested and wait for someone to invite you to the meeting or speak with City-Swimmer to unlock the Gray Fox option, which will also lead you to the meeting.
Regardless of the choice you make, joining the Thieves Guild isn’t as easy as other factions in the game, nor as fast. Yet, if you do join it, there are some interesting quests to pursue, some of which are quite profitable.