After completing the quest A Chance Arrangement, locate the entrance to the Ratway which is below the Plaza and to the South by the waterway. Once inside, be prepared to fight your way through as you encounter resistance by the residents of the Ratway; also be weary of pressure plates, tripwires, hanging oil, and bear traps along the way.
Once you reach the room with the Ragged Flagon door, make sure you flip the lever that drops the bridge to make future trips down here easier; if your lockpicking skills are good enough, there is also a door that you can open making access even easier. Enter the Ragged Flagon, locate Brynjolf who will be discussing the current standings of the Guild with the bartender.
Speak with Brynjolf and he will inform you of three shopkeepers who have decided not to pay their dues to the Guild, and asks that you retrieve what is owed by any means (other that killing of course, that’s Dark Brotherhood territory). Stick around for a moment and ask Brynjolf for any advice he might have regarding getting the debts paid, be sure to receive the three additional (optional) objectives before leaving the Ragged Flagon.
There are a few things that you must remember when shaking down these shopkeeper:
- Shopkeepers can be approached in any order. Just be sure to utilize what you have learned from Brynjolf for a quick and easy resolution.
- It is possible to deal with any of the shopkeepers with fisticuffs tactics; however this must be initiated via conversation, and you only get one opportunity to start the fight. If you attack a shopkeeper any other way, the entire town will turn on you.
- Once two out of the three shopkeepers have been dealt with, word will get around to the third shopkeeper, and they will be much easier to persuade.
- Brynjolf is expecting 300g upon your return (100g from each Shopkeeper). If you spent any of this money before returning to him and have less than 300g on your person, it will become impossible to complete the quest.
Now, with all that being said, let us look at how to get the deadbeats to pay up.
Keerava is the bartender for the Bee and Barb North of the town Plaza. There are two methods to getting Keerava to pay up; you can either start a conversation with her and beat the lizard lady down, or find her lizard lover Talen-Jei and strike up a conversation with him to learn about Keerava’s family in Morrowind. Go back to Keerava and threaten to take a little trip to “that farm in Morrowind” to get her to pay up.
Located in the Pawned Prawn North-West of the Plaza, either beat Bersi down or tell him you’ve had it with his dribble, turn around unsheathe your weapon and start whaling away at the exquisite vase on Bersi’s dresser. Once it has shattered ask him if you need to break anything else and he will quick pay the 100g that is owed.
To the North of the Bee and Barb is Healga’s Bunkhouse; step inside and tell Healga she’ll have to pay in more than just coin to beat her into submission or tell her the Guild is tired of playing nice; look around in her place to locate the Statue of Dibella and swipe it. Tell Haela that this looks like it would go well at the bottom of ….. well, a well. That will get her to pay up. Head back to Brynjolf in the Ragged Flagon to complete the quest, receive your rewards, and begin the next quest Loud and Clear.