Brynjolf will ask for your help framing a fellow merchant nearby. His plan is to have you steal a ring from Madesi while he distracts everyone, then have you pickpocket Brand-Shei and put Madesi’s ring INTO his inventory (it’s really more like reverse-pickpocketing…). It’s not really that hard to do. Before doing it, just make sure you know where Madesi’a stand is and who Brand-Shei is. Oh, and make sure you have some lockpicks…

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After that just tell Brynjolf that you’re ready and he’ll draw everyone in the area around him. Head to Madesi’s stall and pick the sliding drawer, then pick the box you find there. May as well steal everything.

Now go find your target, Brand-Shei (who should be sitting on some boxes to the right). Enter sneak mode and target him behind the boxes (you should be hidden) and put the ring INTO his inventory. You’re basically going to pickpocket the Dark Elf and instead of stealing, head over to your Apparel sub-menu and press the ‘Give’ button on Madesi’s Ring to plant it on his pocket.

After that just talk to Brynjolf for your reward ( 100 gold ). Job well done! He’ll then talk to you about proving yourself ever further, which starts the next quest in this questline: “ Taking Care of Business “.