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Skyrim: The Thieves Guild Main Questline Walkthrough

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A "gamer" since way before the term was coined, I have been playing video games in one form or another since the 1980s.

As you travel through Skyrim, you may hear rumors about a group of thieves who cause mischief and mayhem by stealing things from ordinary and rich alike.

These people make up the Thieves Guild, a group of pickpockets that reside in Riften (for now).

Follow along as we attempt to join their group.

Riften's Bee & Barb Inn

Riften's Bee & Barb Inn

A Chance Arrangement Walkthrough


  • Meet Brynjoff During Daytime
  • Steal Madesi’s Ring
  • Plant Madesi’s Ring
  • Speak to Brynjoff

Your Journey Begins at the Bee and Barb Inn

Visit the Bee and the Barb in Riften, the local pub. Look for a burly man named Brynjolf, as he is your first contact within the Thieves Guild. After a bit of small-talk, Brynjolf tells you that he will let you into the group if you do something to prove your stealthy worth. Head to the marketplace between 8 am and 8 pm and speak with him to begin.

Your goal is to steal a ring and plant it on someone in the center of town. Brand-Shei the Argonian has done something to insult the Thieves Guild, and now you must assist Brynjolf in framing him for theft.

Talk to Brynjolf to have him occupy the townspeople and attempt to open the Novice Lock on the chest hidden in Madesi’s merchant stall. (Make sure that you are crouching and no guards can see you, indicated by a closed eye on your main receptacle.)

Take Madesi’s Silver Ring and sneak behind Brand-Shei, probably still watching Brynjolf talk about the magical potion he has made up. Attempt to pickpocket Brand-Shei while completely hidden, then enter your inventory and place Madesi’s Silver Ring into Brand-Shei’s inventory. This reverse pickpocket now stashes the ring in Brand-Shei’s inventory, in which the Argonian is hauled away to the dungeons of Riften for a week.

Speak again with Brynjolf, and he will express some satisfaction and give you a small reward. He then tells you to meet him in the Ragged Flagon below the city.

Taking Care of Business Walkthrough


  • Locate Byrnjoff at the Ragged Flagon
  • Collect Keerava’s Debt
  • Collect Bersi Honey-Hand’s Debt
  • Collect Haelga’s Debt
  • (Optional) Use Talen-Jei to Get to Keerava
  • (Optional) Smash Bersi’s prized Dwarven Urn
  • (Optional) Steal Haelga’s Statue of Dibella
  • Return to Brynjoff

The entrance of the Ratway is marked on your map, but you must head below the main area of the town, on a lower riverway encircling the area. Head into the front entrance of the Ratway, but be prepared to meet two enemies almost as soon as you enter.

You can kill the people here all the way up to the entrance to the Ragged Flagon, but in the honor of the Thieves Guild, you may choose to sneak through. You will pass through this area again, so make sure to drop the gate nearby for an easy exit. Make your way to the front entrance and head inside.

Find Brynjolf and he will ask you to help with a few Riften citizens that haven’t paid up. Continue to ask Brynjolf about the marks, and he will give you useful information about things that are important to the people involved.

Head out of the Ragged Flagon the way you came in, and head to any of the three locations available: The Bee and the Barb, the Pawned Prawn, and Haelga’s Bunkhouse. After you collect the debts from two of these marks, the third will simply give you his or her money out of fear.

For Keerava, speak with her directly at the Bee and the Barb and she will refuse to pay up. Just beat her up in a brawl or tell her to move and speak with her lover Talen-Jei to see if he has anything to say. He will only open up if you speak with Keerava first, but he gives some information on her family. Use that against her and she will pay the 100 gold pieces she owes.

For Bersi Honey-Hand, find him in the Pawned Prawn and he will refuse to pay. Beat him up in a brawl for fun or walk away and look for his beloved Dwarven pottery across from his merchant table. Hit the urn with anything bulky and it will break after a few hits; even though Bersi and his wife will protest, they will not attack you. After the urn is shattered, head back to Bersi and threaten to break something else. He will pay you the gold he owes.

For Haelga, speak to her in Haelga’s Bunkhouse and beat her up or ignore her stubborn refusal to pay. Find the Statue of Dibella and steal it for ransom. Get the gold from her in trade for the statue.

Return to Brynjolf in the Ragged Flagon and he will expect the full payment of 300 gold, so don't take any for your own use. He will then give you some gold and your choice of a few potions for a reward.

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Read More From Levelskip

You’re now an initiate into the Thieves Guild, so be prepared for some major loot!

Loud and Clear Walkthrough


  • Follow Brynjoff
  • Listen to Mercer Frey
  • Talk to Brynjoff
  • Burn Three Beehives
  • Clear out Aringoth’s Safe
  • (Optional) Speak to Vex about Goldenglow Estate
  • Learn More about the Thieves Guild from Vex
  • Learn More about the Thieves Guild from Delvan
  • Retrieve the Thieves Guild Armor from Tonilla
  • (Optional) Enter Goldenglow Using the Sewer
  • (Optional) Obtain the Key to Aringoth’s Safe
  • Return to Brynjoff