This is the second quest pertaining to the Thieves Guild, acquired by Brynjolf.
1. Locate the Ragged Flagon and speak with Brynjolf
- Locate the Ratway, located on the lower levels of Riften
- In the Ratway, you’ll encounter a few aggressive bandits, kill them.
- Shortly, you’ll locate the entrance to the Ragged Flagon and find Brynjolf at the bar.
2. He will instruct you to collect debts from 3 business owners in town.
- Keerava’s debt: When arriving, speak first to male Argonian just inside the door. He’s her love interest. Choose the dialog option about talking some sense into Keerava. Then speak with Keerava to convince her to pay you
- Bersi Honey-Hand’s debt: Pull out your weapon and “attack” the urn in front of him. He’ll make some comments, continue until it breaks. Then speak with him and he’ll pay.
- Haelga’s debt: Around the corner from her counter is the statue. Be sure to sneak first so you don’t get a bounty. Steal the statue. Then speak with Haelga to receive the debt payment.
3. Return to Brynjolf in the Ragged Flagon. He’ll invite you to walk with him. You’ll meet an NPC named Mercer who gives the follow up quest “Loud and Clear” and welcome you to the guild.