A Chance Arrangement

A Chance Arrangement is the first quest you do for the The Thieves' Guild

You get the quest from Brynjolf who is usually found in the Riften market or in the inn.

Brynjolf at his stall in the market

In this quest, Brynjolf wants you to steal a ring from Madesi and slip it into the pocket of Brand-Shei. He explains that he will be in the Marketplace from 8 am to 8 pm. He will be at his "stall" during this time. Just approach him and talk with him to start next part of the quest.

The Strongbox

Once Brynjolf creates a distraction, you sneak behind Madesi's stall and steal the ring from the Strongbox. Madesi's stall is to the South of Brynjolf's. Slip behind it and go to the sliding wicker screen. Pick that lock. Inside you will find the Strongbox you are looking for: Madeesi's Strongbox. Inside it is Madesi's Silver Ring. Take that then head over toward the crowd.

Bramd-Shei listening to Brynjolf

Find Brand-Shei who is to the East of Brynjolf's stall. Then you can sneak behind Brand-Shei and put the ring into his pocket. This is an easy job which can be made easier with anything that augments your pickpocket skill. Still, it is recommended that you save beforehand, just in case you need to retry. The quest will still complete if it fails. Once I item is planted then Byrnjolf will stop talking and the crowd will disperse.

After you finish this quest you will be given the next quest in the Thieves Guild Series, Taking Care of Business