Currently serving as headquarters for the Thieves Guild, here is where the Dragonborn can receive guild quests from Vex and Delvin Mallory, and both purchase thief supplies and fence stolen items with Tonilia.
For every special job the Dragonborn completes for Delvin Mallory, a merchant opens his business next to the Ragged Flagon. There are four in total: an alchemist, an armorer, a fletcher, and a blacksmith.
- Arnskar Ember-Master (Smithing)
- Herluin Lothaire (Alchemy)
- Syndus (Archery)
- Tonilia (Fence)
- Vanryth Gatharian (Weapons and armor)
- Galathil (Character appearance editor). Only available in Dawnguard.
- Advances in Lockpicking can be found in The Ragged Flagon - Cistern in the room to the north-east on top of a barrel.
- Occasionally, members of the Thieves Guild will practice Archery skills around the main room of the cistern, where the arrows may be retrieved from the training posts they were shot at.
- Next to the door that leads to the Ratway Vaults, there are two wine bottles. These bottles can be used as an infinite wine source, as when they are picked up, they will respawn a few days later and can be collected again. This is a never ending cycle.
- Sometimes the Dragonborn can hear a conversation between Tonilia and Delvin. Tonilia says she might buy some goods off of Delvin, and Delvin retorts by saying she should take some jobs to help the Guild. Tonilia says she might take him up on the offer in the future.
- Sometimes a conversation can be heard where Delvin tries to seduce Vex. Vex will reply positively, only to scold Delvin saying that it will only happen when he is in the grave.
- Two notes can be found on one of the tables. One discusses a stash of arrows and the other is a warning from Vex to Delvin if she catches him peeking at her bathing again.
- After the quest Stabilized, Sapphire will be found in The Ragged Flagon, after previously being located in The Bee and Barb in Riften.
- This is the only tavern located underground.
- Most items in the tavern area will be free to be taken without stolen tag after the completion of all city influence quests including Deliver Moon Sugar to Ri'saad.