A Chance Arrangement

Given by Brynjolf, who is at the town square in Riften or in The Bee and Barb. This is the first quest needed to join the Thieves Guild.

Journal Entry
"Brynjolf in Riften seems to be involved in some nefarious activities and has convinced me to take part in one of his schemes."

Objectives

 * Meet Brynjolf during daytime.
 * Steal Madesi's ring from his strongbox.
 * Plant Madesi's ring on Brand-Shei.
 * Speak to Brynjolf.

Walkthrough
The quest begins once the dragonborn speaks to Brynjolf and agrees to help him. Brynjolf can initially be found during daytime or nighttime. He can be most commonly found in The Bee and Barb or walking around the Riften Marketplace.

Stealing

 * When the dragonborn tells Brynjolf he/she is ready to get started, Brynjolf will call everyone over to him. He starts telling people about some valuable potions he is selling for 20 septims. Wait until everyone is distracted and not moving anymore, listening to Brynjolf. The ring is stolen from Madesi's strongbox, located underneath his booth behind a locked sliding door. The dragonborn may choose to either pickpocket a key from Madesi or pick the lock. The sliding door and lock may be unlocked the night before when there is less people around. Steal the ring, along with other items, then sneak over to the crates behind Brand-Shei.
 * Pickpocket Brand-Shei, but instead of taking from him, plant the ring on Brand-Shei. He's sitting down watching Brynjolf talk and is easily pick-pocketed from behind the boxes with a high success rate. Brynjolf should stop the distraction once this is completed, and, after turning in the quest, Brand-Shei will be approached by a guard and arrested. Planting the ring on someone else does not get the person arrested instead.


 * Talk to Brynjolf again, and he will congratulate the dragonborn.

Not stealing or failing
Failing to complete the assignment does not prevent the dragonborn from continuing the quest line. Brynjolf will express disappointment, but will state that he believes the dragonborn still shows potential. The following scenarios are possible:


 * Getting caught stealing during the distraction will result in failing the quest. If the dragonborn has earned the title of Thane of Riften, he/she can use this title to get out of being caught during this quest, though it may not be recommended since thanes only get one pardon.


 * The dragonborn can remove Madesi's ring from his/her inventory anytime after stealing it, and tell Brynjolf that it was lost it. The "Plant Madesi's Ring" objective gets marked as failed, but the mission can still be completed, allowing the dragonborn to continue and join the thieves guild.


 * The distraction will go on for quite some time, and if the dragonborn doesn't plant the ring on Brand-Shei before Brynjolf finishes, the group will sit in silence sometimes until the quest is completed. The quest will fail after some amount of time, however. Leaving Riften and going to the stables once and returning may still have the distraction running, but after leaving a second time the quest may end in failure. If this occurs, Brynjolf will express disappointment, as noted above, saying that he could not keep up that distraction for too long, but the quest line will still be available.
 * Another way to complete this quest quickly and safely, without breaking any laws: After the distraction starts, simply wander around and go inside any door around the market. This will cause the planting assignment to fail, while strangely, the stealing assignment will still be completed. In this manner th dragonborn can still complete the quest by talking to Brynjolf without any stealing or pick-pocketing. This will not result in breaking the questline.

In any scenario above, the dragonborn will return to Brynjolf without getting paid and continue the quest-line while keeping Brand-Shei as a vendor.

Trivia

 * If the dragonborn has a follower, the follower may mingle with the rest of the crowd. The follower will follow the dragonborn again once the crowd separates again.

Behind the Scenes

 * Unless otherwise stated, the information above was obtained from in-game play or from The Elder Scrolls V: Skyrim Creation Kit.