To begin this quest, find any of the below items (called “Unusual Gem” until you begin the quest). Find Vex in The Ragged Flagon and return to her when you have all 24.
Vex will have you travel to Tolvald’s Cave, in which you have to find the Crown of Barenziah at the end. Bring the crown back to Vex and she will imbue you with the perk: Prowler’s Profit, which increases the rate of gems found in Skyrim.
Ansilvund- burial chamber
College of Winterhold- Arch-Mage’s Quarters
Dainty Sload- Captain’s Quarters
Dark Brotherhood Sanctuary- Astrid’s room
Dead Crone Rock- altar
Fellglow Keep- table in front area
Hob’s Fall Cave- sleeping area
Markarth- Master Bedroom in Treasury House
Markarth- Dwemer Museum
Pinewatch- treasure room
Rannveig’s Fast- table near water
Riften- Jarl’s quarters in Mistveil Keep
Riften- master bedroom of Black-Briar Lodge
Solitude- Master bedroom of Proudspire Manor
Solitude- Jarl Elisif’s chambers
Stony Creek Cave- Wizard’s cave
Sunderstone Gorge- alter in front of word wall
Thalmor Embassy- bedroom in Elenwen’s Solar
Whiterun- Kodlak’s bedroom in Jorrvaskr
Whiterun- Crypt in Hall of the Dead
Whiterun- Jarl’s bedroom of Dragonsreach
Windhelm- bedroom of House of Clan Shatter-Shield
Windhelm- Wuunferth’s chambers in Palace of the Kings
Yngvild- Throne Room
Moon Sugar Rush
If you speak with Tonilla after becoming a member of the Thieves Guild, she will ask you to deliver a bag of Moon Sugar to a road merchant named Ri’saad. If you do this, any Khajiit caravaners will now buy stolen goods.
In order to become the Guild Master and acquire all available fences in cities, you must do a five Radiant Quests each in these four cities: Markarth, Solitude, Whiterun, and Windhelm. Once you reach five quests in a particular city, speak with Delvin and he will inform you of a quest for an influential member of the stronghold. All initial jobs need to be done in stealth and without killing anyone.
NOTE: If you need to get jobs in certain towns, save before you speak with the quest-giver and reset your game to randomize the Radiant Quest components.
The Numbers Job- Head to a business and change the ledger inside.
The Fishing Job-Pickpocket a special item from a citizen of Skyrim
The Bedlam Job- Steal a certain amount worth of goods
The Burglary Job- Break into a house and steal an item
The Shill Job- Put a stolen item into the home of a person
The Sweep Job- Take items from a house in Skyrim
The Heist Job- Steal a valuable item from a shop
City Influence Quests
As you complete the 5 Radiant Quests per city and finish the quests for the future fences of the town, you get benefits for helping the Thieves Guild further its reach.
One City Quest Finished= Fences have 1500 available gold and new archery merchant in Riften
Two City Quests Finished=Fences have 2250 avaiable gold and new blacksmith merchant in Riften
Three City Quests Finished=Fences have 3000 available gold and new apothecary in Riften
Four City Quests Finished=Fences have 4000 available gold and armorsmith in Riften
In each city that you complete the City Quest, you will be able to bribe and persuade guards to take care or overlook crimes. If you wish to pay off a bounty without losing your stolen items, you can barter bounties for half price with guards as well. Finally, Thieves Guild Shadowmarks appear in town on barrels with random treasures that refill.
Silver Lining (City Quest for Markarth)
Speak to Endon the Silversmith
Recover Endon’s Silver Mold
Return to Endon
Speak with Delvin after completing at least five Radiant Quests in Markarth. He will direct you to Endon, who needs help with some bandits. Find Pinewatch and head to the locked house on your map. Break into the average lock (while hidden from view, of course), and do with Rhorlak what you need to in order to open the fake cabinet across from the fireplace. Head through the next open room and find the entrance to the Sanctuary inside.
Kill or sneak past some bandit ahead and head west to find a bandit camp. Take down Rigel Strong-Arm and take the keys from her to access the next room through a wooden door. Sprint quickly across this bridge and dodge the traps ahead to find the room containing your target item, Endon’s Silver Mold, and the Silver Candlestick you can sell to Delvin back in the Ragged Flagon. Leave the cave and make your way back to Endon in Markarth to complete the quest and unlock him as a Fence. He is generally walking around the path leading towards Vindrel Hall, the purchasable home in town.
The Dainty Sload (the City Quest for Solitude)
Speak with Erikur
Acquire Balmora Blue
Plant the Balmora Blue
Return to Erikur
After completing 5 additional quests in Solitude, speak with Delvin and he will tell you about a man named Erikur in Solitude. Erikur needs you to plant some contraband on the captain of the Red Wave, a ship found outside of Solitude.
To get the Balmora Blue, find Sabine on one of the ships in the east Empire Company Warehouse and either buy it or steal the key to find a safe containing it in the basement of the ship. You must be careful on your way to the safe, as anyone who sees you will automatically attack you. Wipe them out if you want, but get the item from the safe under the water close to Sabine however you choose.
Head over to the Dainty Sload, where you must find your way to the chest in the Captain’s quarters. The easy method is to head in and kill everyone on board, but you can also attempt to sneak to the room in the bowels of the ship if you can. After you plant the Balmora Blue, head back to Erikur in Solitude to finish the quest and open Erikur as the fence of the town.
Speak to Olfrid Battle-Born
Steal the Letter Incriminating Arn
Forge the Prison Registry
Return to Olfrid Battle-Born
After finishing 5 additional quests for Whiterun, Delvin will tell you to head to Dragonsreach to steal an important letter and forge it in order to save someone important to Olfrid Battle-Born in town. Try not to make anyone mad and stealthily head towards the Jarl’s private quarters to steal the Letter from Solitude. Return the letter to Olfrid to unlock him as a fence in Whiterun.
Speak to Torsten Cruel-Sea
Speak to Niranye
(Optional) Discover Leverage to Sway Niranye
Travel to Uttering Hills Cave
Recover Fjolti’s Silver Locket
(Optional) Destroy the Summerset Shadow’s Banner
Return to Torsten Cruel-Sea
After completing 5 additional quests for Windhelm, Delvin will point you towards Torsten Cruel-Sea in the area around the house of his family. Find Niranye in town and attempt to get information from her through persuasion or intimidation. If you are unable to get her to talk the first time around, you can find a note in her safe in the basement of the House of Clan Cruel-Sea to make her reconsider. After she gives you some information about the Summerset Shadows in Uttering Hills Cave, head over that way to look for the missing locket for Torsten.
Head down a staircase outside to find the entrance to the thieves’ eating area. If you want to, set fire to the banner and then find Linwe in a room off the main area. Kill him and take the locket (and any of his named thieves armors) off him and return it to Torsten in Windhelm. If you didn’t kill Niranye, she is now a fence inside Windhelm. You can find her at her stall in the market or at her home in the southwest of town.
Leadership Quest: Under New Management
After you complete 5 additional quests and their subsequent city quest for each of the towns of Windhelm, Whiterun, Solitude, and Markarth, and also completing the main questline ending with the Thieves Guild Quest – Darkness Returns, speak with Brynjolf about becoming the new leader of the Thieves’ Guild. Meet the group in the center of the Cistern for a small ceremony and presentation of a few items. Speak with Tonilla afterwards and she will give you the Guild Master’s Armor, and now you have access to the Tribute Chest in the area, which is refilled with sellable gems and gold.
Serve Nocturnal well, Boss.
- Skyrim: Thoughts on Radiant Quests (zpte.wordpress.com)
- Skyrim and the Compass to Nowhere [The Elder Scrolls] (kotaku.com)