Everything you need to know to join the Thieves Guild in Oblivion Remastered.
Oblivion Remastered brings back the classic RPG with all its old content and refines it for the modern generation. And what’s an Elder Scrolls without the many side quests?
The Thieves Guild is one of the factions of the Elders Scrolls, and the questline to join them is one of the many fun side quests in the game.
Moreover, joining the Thieves Guild and completing the quests they give you will reward you with exclusive items, which are especially useful if you’re planning on a stealthy build. You’ll also get the ability to sell stolen items, making it even more lucrative to be a thief.
So, whether you want to be a cat burglar, a sneaky assassin, or just want to join the Thieves Guild for the fun of it, in this article, we break down exactly how to join the Thieves Guild.
How to Join the Thieves Guild
There are two easy methods to join the Thieves Guild in Oblivion. One involves investigating the Gray Fox, and the other involves you going to prison. Both of these will start you on a chain of quests that take you to a meeting in the Garden of Dareloth.
The Gray Fox

This method involves investigating the wanted posters of The Gray Fox that are found around the Imperial City.
Read any of these wanted posters and start a dialogue with the city guards and ask them about the Gray Fox. Repeat this until you hear “The beggars love him, especially in the Waterfront.“

You can then head to Puny Ancus in the Waterfront District or Simplicia the Slow in the Market District. You’ll have to have a high enough disposition with either of them (70 Disposition) to ask them about the Gray Fox, and choose the “Yes, I want to work with him” option. They will then direct you to the Garden of Dareloth where you can begin your initiation into the Thieves Guild.
Going to Prison
The first step in this method is to get arrested and sent to prison. There are many crimes you can do to get sent to prison. But if you want to keep in theme, you can just steal something and wait for the guards to arrest you. Choose the “Go to Jail” option when confronted.

Once you’re inside your jail cell, interact with the bedroll, and a prompt will shout out reading “Do you just want to serve your time?” Select Yes.

After you leave jail, wait for Myvryna Arona to appear and talk to her. She will give you note that triggers the Finding the Thieves Guild quest. This directs you to the Garden of Dareloth.
You can use the wait mechanic and select 4 hours so that Myvryna shows up.
May the Best Thief Win

Then, head to the Garden of Dareloth at midnight and wait for Armand Christophe to approach. Talk to him about the Gray Fox, then choose the “Join the Thieves Guild” option. You’ll have to persuade Armand to like you enough (60 Disposition) before you can do this.
This will give you the May the Best Thief Win quest, where you’ll have to race against two other thieves to steal Amantius Allectus’ Diary.

Allectus’ house is in the Temple District. After you steal the diary, return to Armand to complete the quest and your initiation into the Thieves Guild.