He will instruct the Dragonborn to collect debts from three business owners in town. Exit the Ragged Flagon by the front door, then go through the second archway on the right wall. Pull the lever to drop the draw bridge across the gap and follow the path to exit the Ratways.
Whatever order the debts are collected in, the third target will have heard about the previous two and chooses to simply hand over the money when spoken with about it.
Speak first to Talen-Jei, a male Argonian. Talen-Jei is likely just inside the door, or upstairs sleeping in his room. Choose the dialog option about talking some sense into Keerava. Then speak with Keerava about giving Brynjolf to convince her to pay the dragonborn.
Alternatively, choose to brawl with Keerava. Win the fight and she'll pay. Accidentally hitting another patron during the fight will give a bounty, and cause Keerava and everybody else to be hostile.
Kill Keerava and loot the 100 gold, but Brynjolf will not be happy about this.
Around the corner from her counter is the statue. Be sure to sneak first to avoid a bounty, and steal the statue. Then speak with her to receive the debt payment.
Brawl with her and she'll hand over the money when defeated.
The dragonborn can kill Haelga and loot the 100 gold, but Brynjolf will not be happy about this.
Talk to Haelga but do not loot the statue, brawl or kill her. Then collect debts from Keerava and Bersi Honey-Hand (After brawling with Bersi), tell Haelga you have a message from Brynjolf and she will instantly pay up.
Once the debts have been collected, return to Brynjolf in the The Ragged Flagon. He will invite the Dragonborn to walk with him. Mercer Frey will give the follow up quest Loud and Clear and welcomes the dragonborn to the guild.
Always add 360 , PS3 , and PC to clarify which system the bug appears on.
Click to show Bugs
During this quest, it is possible that after failing to collect Keerava's debt during the speech options, she will run off and disappear. So far, there is one fix: reloading from an autosave. There is no known way to fix this problem without reloading the autosave. The dragonborn will be able to collect the other debts and hand them in, but Keerava will be gone forever. Although not proven, she may be able to reappear after doing some quests relevant to her or waiting for a few days.Check into the Bee and Barb in Riften anytime the dragonborn is near it just to check if she has spawned again. This bug will prevent the dragonborn moving any further into the Thieves' Guild questline.
If the brawl option is selected, the Dragonborn's opponent may draw a dagger and attack with it. This usually only happens with the first character being shaken down. "Sheathing" the fists will stop the attack and the brawl can be restarted and the dagger may not be drawn again. However, if it is Keerava, bystanders will kill her immediately, causing the quest to be blocked from further progression. Load a previous save and select Bersi Honey-Hand as the first encounter. (Be sure no one other than his wife is in the shop, she will also attack, but will stop along with Bersi when the fists are put down.)
Though the cause is unknown, there is a break in this quest line where Brynjolf keeps standing in the stand like he is still giving an announcement to the traders from the previous quest, unwilling to go anywhere else.
This can be resolved by simply going to the Ragged Flagon and then bringing up the console with the tilde key and typing "player.placeatme 1b07d". This will summon him in front of the dragonborn and allow the quest to progress.
If Brynjolf walks to the door but then the thieves inside the Cistern attack the dragonborn: After completing the "Taking care of business quest", once Brynjolf has told the dragonborn to follow him: 1. open the command console. 2. type <setstage TG03 10>, this will skip the loud and clear quest and start the dampening spirits quest, but everyone in the guild will still attack the dragonborn. 3. type <player.addfac 29da9 1> this will make the dragonborn a member of the thieves guild.
Alternately, punch him while unarmed once and immediately stop. This can sometimes jolt him out of his paralysis and walk towards the secret entrance. The dragonborn may also have to open the secret entrance to the Cistern. Simply go through the fake storage closet and open the hatch to Riften, then pull the lever. The dragonborn may also have to wait for him to enter the cistern. Simply use 'T' to wait for an hour, and he should go inside, and the quest will continue normally.
Also, if the dragonborn hits him and cause a fight, have him chase the dragonborn to the Ratways Door, then beat him down and unequip a weapon and heal him using "Healing Hands". (When healed he shouldn't attack the dragonborn further.) To get him through the door the dragonborn needs to initiate conversion and then exit before he finished talking and enter the Ratways then repeat to get him to follow the dragonborn to the Ragged Flagon.
The alternative way to do this is to sprint into Brynjolf and make him step back and continue to do so until he is at the door to the ratway, then open the door. Immediately talk to Brynjolf which will make him appear in the ratway. Then push him a bit more further and save. Punch him once, unarmed, and proceed to run to the ragged flaggon and enter the bar (Make sure he is close by at all times.) then knock him down with unrelenting force (If that doesn't work use fists remember FISTS are what do it don't use swords, to beat him down, then quickly lower the dragonborn's fists and quickly talk to him) same applies to using unrelenting force but without the punching.
Solved by punching Brynjolf out of sight from a guard, and then attacking a townsmember where a guard CAN see the dragonborn. After accepting the fine and being transported to the keep, Brynjolf was back to normal. (Xbox 360)
Solved by clearing the system cache (Xbox 360).
When the dragonborn is walking with Brynjolf at the end of the quest, sometimes the Cistern door is locked. Reloading seems to fix this. (Xbox 360)
Talk to Haelga last so the dragonborn can extort the coins from her without her taking the statue, she will take the statue anyway. (PS3)
The Quest, Rescue Mission previously prevented this quest from being completed. As of Skyrim Patch 1.5, this problem is resolved.
While collecting Keerava's debt, it is possible to choose an option to say that it doesn't matter for the dragonborn to collect the debt. Once the dragonborn exits and talk to her again, the dialog bar won't pop out, thus making it impossible for the dragonborn to continue any further.
Sometimes (probably due to discovering the Flaggon beforehand), the dragonborn will be considered as a trespasser upon entering the Cistern, thus rendering it impossible to complete the questline, because everyone there, including Mercer and Brynjolf, will attack. This can be quite ironic because the thieves start yelling "Guards! Trespasser!". (needs a fix)
360 After the quest, Bersi Money-Hand will not mention about the debt like it never happened.
More of a illogical circumstance than a bug: the debts from all three people total 300 septims... Which the dragon born could easily pay off though there is no option to do this.