The Elder Scrolls 5 - Skyrim - Thieve's Guild Quests


This quest, a Chance Arrangement, is received after having talked to Brynjolf in the Riften marketplace and accepting his offer to complete a small task for some money. You are asked to plant a ring belonging to a local vendor, Madesi, into the pocket of another vendor, Brand-Shei. Brynjolf will provide you a distraction to do so and will ask you to do this task without being noticed. This is a detailed guide on how to complete the quest in the fastest manner.


Talk to Brynjolf

Steal Madesi's Ring

Plant Madesi's Ring on Brand-Shei

Speak to Brynjolf


100 Septims
Opportunity to join the Thieves' Guild through the quest, Taking Care of Business

This is the first quest belonging to the Thieves' Guild questline, and may be acquired when visiting the marketplace in Riften. To start the quest, you need to visit the marketplace in Riften and wait for a fellow, named Brynjolf, to come and talk to you. If you want to save time, you can just find him in The Bee and the Barb tavern and start a conversation with him yourself.

When you speak with him, he will mention your talent at discovering his ruse at the main gate of Riften (if you persuaded the guards to let you pass) and talk about how he suspects that your inventory consists of stolen goods and how you can earn more if you help him out with a small task. This is the start of the Thieves' Guild quest series. Accept the offer and he will ask you to steal a ring from a nearby vendor, Madesi, and plant that ring on Brand-Shei, who is also a vendor in that area. He explains that this is a warning for Brand-Shei to not meddle into other peoples' affairs. He will ask you to tell him when you are ready so he can provide a small distraction for you to complete your task. Make sure you are stocked up in lock-picks before you do so and, if you desire, equip any enchanted items that can help Lock-picking or Pick-pocketing.

Save your game and once you are ready, talk to him once more and he will run off to perform the distraction (a speech on the other side of the marketplace). All vendors and characters in that area walk towards his podium, where he is announcing the miracles that a new product of his can perform. Use the spell Clairvoyance or the compass and objective marker to find your objective, which is Madesi's stall. Once you reach the booth, go into sneak mode and wait until you are unseen by all. The bottom sliding door is locked, which is a novice lock and depending on your level, it might be a breeze. If not, just try your best with the lock-picks you have and use any buffs, potions, spells, or enchantments you may have. Once the lock is picked, make sure you are hidden before picking the lock of the small chest.

Note: It is possible to fail the quest, but Brynjolf will appreciate your efforts and let you start the Thieves' Guild Quests.

After picking the lock of the small chest, retrieve the ring from inside and leave the area. To find Brand-Shei, take a glance at your objective marker or use Clairvoyance to find him. You could find him sitting on a couple of boxes, listening to the speech, opposite to Brynjolf. Sneak behind him, using the stalls and the few boxes nearby to stay out of sight, enter the small gap between the boxes and the wall to find yourself directly behind Brand-Shei, yet remaining hidden the whole time. Pickpocket him through a small crack between the boxes and place the ring in his inventory (remember equip and place are different buttons when pick-pocketing).

After completing the task, Brynjolf will stop his speech and everyone will exit the area. Walk over to him and he will congratulate you on your success and hand over 100 septims for you help. He will also extend an invitation to you to join the Thieves' Guild and offer you the next quest in the Thieves' Guild quest series, Taking Care of Business.



Locate Brynjolf at the Ragged Flagon

Collect Keerava's debt

Collect Bersi Honey-Hand's debt

Collect Haelga's debt

Return to Brynjolf

After A Chance Arrangement, Brynjolf invites you to pay him a visit at the Ragged Flagon, which is deeper in The Ratway. When you reach him, he mentions a little debt collection exercise and makes you the pointman for the job. Go to each of the people (all located in Riften). The ladies (Haelga and Keerava) might need a little more than vocal persuasion.If you do not want to be in fistfight with Haelga you can grab a Dibella's statue and then talk to her. Bersi will just give up his payment with no hassle -- just the way it should be.

Note: If Bersi's wife Drifa is in the room your options are to forgive his debt or brawl.

With their dues collected, return to Brynjolf.



Follow Brynjolf

Listen to Mercer Frey

Talk to Brynjolf

Burn three bee hives

Clear out Aringoth's safe

The objective here is to clear out a safe and light three beehives ablaze to send a message for Maven Black-Briar to the owner of the Goldenglow Estate.

Follow Brynjolf to the Cistern and listen to the briefing by Mercer Frey. Next, talk to Brynjolf. He will suggest that you talk to Vex. Go and speak with her and find out about the sewer that leads to the back door of Goldenglow Estate. Don't forget to talk to Tonilia to get your guild armour set. Bring plenty of lock-picks and a torch (needed to burn the beehives)

If you decided to enter through the sewers, you have to kill a few Skeevers along the way and avoid a fire trap. If you follow the marker leading to Goldenglow, you'll exit beside the estate's back door. Pick the lock and head inside. Move from room to room, silently sneaking by the guards. Just consult your local map to find the marker and head to its direction to find an iron bar door. If you want, you can get the key to the safe from Aringoth himself. You can persuade him or kill him. You can find him on the second floor. You can also pickpocket or loot the cellar key from him.

The cellar door can be unlocked by picking the lock or getting a key from a guard (or Aringoth himself). Continue to the basement and make your way to the safe. You can open this easily if you have the safe key. Otherwise, your lock-picking skill will need to be rather high for this endeavour to be successful. After clearing the safe, you can open the nearby iron door and head back to the sewers.

Head outside to the beehives and equip your torch or a flame spell. Light up only three of them on fire. Rather than fight the guards you could run away or if you're competent enough, take them out.

Head back to the guild and talk to Brynjolf, complete the mission and get your reward.



Speak to Maven Black-briar

Speak to Mallus Macius

Speak to Sabjorn

Poison the Honningbrew Vat

Poison the Nest

Attend the tasting ceremony

Speak to Mallus Macius

Identify Sabjorn's silent partner

Brynjolf tells you that Maven Black-Briar, the influential contact that you did the previous mission for, wants to talk to you about a job. Head out to the Bee and Barb, where you will find Maven on the second floor of the inn. She wants you to investigate an up-and-coming meadery called The Honningbrew Meadery.

She sends you to Whiterun to talk to her contact in the Bannered Mare, Mallus Maccius. Mallus cooks up a plan to poison the brewing vats and gets your ticket inside, for you see the owner has a bit of vermin problem that has to be stopped.

After talking to Mallus Marccius, he sends you to Sabjorn himself. Head to the Honningbrew Meadery and talk to him to offer your help with his vermin problem. He'll eventually agree, so take it upon yourself to purge his place of Skeevers, Frostbite Spiders and any other creatures inhabiting the place. If you can successfully persuade or intimidate Sabjorn during your initial conversation, he will give a half-payment up front of 500 gold.

When you get close to the nest, you will run into a lunatic named Hamelyn, a disgruntled alchemist breeding a Skeever army to get revenge on the people who wronged him in the past. Hamrlyn has a very powerful magic attack and can be a tough fight. Do whatever you can to avoid getting hit by his attacks and take him down quickly. You can also drink potions that will increase your various resistances.

Once you have killed him then poison the nest and proceed into the basement of the brewing room. Go upstairs and activate the lid on the marked pot to put the poison. Now grab the key beside the door and exit.

Talk to Sabjorn who says your payment will have to wait until after the captain leaves. Now is your chance to sit back and watch your handiwork when the Captain tastes the mead and subsequently arrests Sabjorn. After they leave, talk to Marcus who will give you the key to Sabjorn's office to find the information that Maven wants.

Go upstairs and find the promissory note. Sitting on the table is a book A Game at Dinner, worth a lot of money. There is another notable loot here behind an expert locked door, the Honningbrew Decanter which you can sell to Delvin for a good price. Return to Maven, but not before Marcus offers to be your fence in Whiterun. Once back in Riften, talk to Maven and give her the information you found. She bounces the information back to the Guild, so speak to Brynjolf to end the quest.



Speak to Mercer Frey

(Optional) Speak to Brynjolf

Speak to Gulum-ei

Get information from Gulum-Ei

Shadow Gulum-Ei

Confront Gulum-Ei

Gulum-Ei can be found in the a small alcove within Solitude's inn, The Winking Skeever. If your Speech level is high, you can easily get the needed information from him through persuasion (intimidation won't work). Otherwise, you'll have to steal a case of Fire Wine from within Blue Castle in Solitude. This is fairly easy, as the case is sitting out in the open upon a small shelf in the left-hand hallway off of the main room. There are guards roving about so sneaking is a good idea when you snatch it.

Once he gets up to leave, you are given the objective to shadow him. He ends up leading you to the East Empire Company Warehouse, where you must pick the door, or if your skill is high enough, you can pickpocket the key while shadowing him and use the key to enter.

If you're following Gulum-Ei closely, you should still be able to keep your eyes on him as he walks inside the warehouse. The guards here are hostile so if they spot you, kill them immediately. Continue following Gulum-Ei until he exits to Brinewater Grotto. If you ever lost sight of him, take note of the stairs leading to the water and the ramp across it with a draft blowing.

Upon entering, you're notified to having completed shadowing Gulum and are thus given the new objective to confront him. There is no going back at this point, as the door locks behind you and requires a key to unlock. Making your way through the Grotto, you will come across multiple pairs of Bandits and Highwaymen whom you are free to kill as you wish without consequence to the quest. Near the end you will come across a grotto with some cages and shelves containing a few chests, some armour and other moderately valuable loot. Gulum is standing there with a bandit. Attack the bandit and Gulum will run away from the fight. After you have dispatched the bandit, talk to Gulum. You can choose to kill him, but if you do, you will not get a reward. Let him live and you have a new fence (buyer of stolen goods).

After you have finished talking to him, the quest is updated to go talk to Mercer. To get out of the room there are three levers: the middle of which opens a hole in the wall towards the way out, while the other two open the empty cells. Head back to Riften and talk to Mercer to complete the mission.

Your reward for the quest is an upgraded piece of Thieves Guild armour. To receive it you must speak to Tonilia and trade in of your pieces for an upgraded version. You can choose which piece you want to upgrade.

Completing this quest launches the next quest, Speaking With Silence.



Meet Mercer Frey outside Snow Veil


Enter Snow Veil Sanctum

Find Karliah

Speak to Karliah

Make your way to Snow Veil Sanctum and have a chat with Mercer who is waiting outside. Mercer will inform you that Karliah is hold up inside Snow Veil Sanctum, so lead the way to the door, which Mercer will unlock, and head inside.

Once inside follow the path around to an open area. Continue into the next room with a chest in the centre. Two Draugrs will pop out, so take care of them and pull the chain to open a gate across from you for some goodies. Push on into the next room to find dead bodies lying about. On the wall next to the gate there will be a chain that needs to be pulled to open the gate, but watch out for the giant wall of spikes that swings towards you as you pull the chain.

Head downstairs to see a Draugr standing in a wall. Take advantage of its momentary immobility and light him up with your weapon of choice. Once he's taken care of continue on around through the winding tunnels. There is a door on your right that can be picked for some potions. Continue on and watch your step as there are bear traps set up, and Draugrs about. After killing all the Draugrs you should eventually come to a gate. Use the chain on the left to open it.

Head down the stairs and either head straight to pick the door for some items, or head left and take care of the three or so Draugrs. Once they've been eliminated press on through the gate and down the stairs, and prepare yourself for a fight. There's about five Draugrs that need to be taken care of. Watch out for their shouts and the frost creatures that they spawn.

Once they have all been dealt with either head up the wooden stairs straight across from where you entered this room for a Model Ship that can be taken to to Devlin, or head up the stone stairs on your right for the quest. Note that once you take the model ship it will ignite the oil on the floor so be careful

Once you are in the next area of Snow Veil Sanctum prepare for a pretty tough battle with some Draugrs. Take care of the three Draugrs here and head down the stairs to fight four more. After they've been put down head through the gate, watch the pressure plate, continue on through the corridors killing any Draugrs you see, and continue on through the double doors. Kill the Draugrs in here and head to the back of this room to find a new shout: Disarm. From the place where got the shout head up the stairs for a chest, or go right through the gate.

Once through the gate, press on through the corridors avoiding the bear traps and walk to the door that needs a claw. Obviously you do not have the claw, but do not worry because apparently Mercer can pick any lock. After Mercer opens the claw door head through and watch the events that unfold.

Once you're outside, Karliah will talk to you which will wrap up the quest and initiate the next quest, Hard Answers.



Speak with Enthir in Winterhold

Speak with Calcelmo in Markarth

Gain entry to Calcelmo's Museum

Obtain Calcelmo's Falmer Translating Guide

Create a duplicate of the Falmer

Translating Guide

Return to Enthir

Speak to Enthir

Speak to Karliah.

Travel to Winterhold and follow the marker (or consult your local map) to locate Enthir. Talk to him and show him the journal. After learning it was written in Falmer, he will refer you to Calcelmo in Markarth. You'll find him inside the Understone Keep.

Calcelmo will refuse to show you his work unless you convince him through persuasion, bribery or intimidation. Once you successfully get his approval, you'll receive the key to the Dwemer Museum. (Note: If your persuade, intimidate, and bribe do not work, you may also obtain the key legitimately by completing Calcelmo's spider side quest, by stealing it off the table nearby, or completing the "Book Of Love" quest.) Follow the marker to find the Museum's entrance. If ever a guard stops you, just ignore him and open the gate anyway. You can also completely skip speaking to Calcelmo, and just break into the museum. If you go this route, you will have to sneak by or kill the museum guards.

Once you're in the museum, go straight ahead and unlock the door leading to Calcelmo's laboratory. Once inside, check the table to the left to find a Spider Control Rod. A mechanical spider will appear and you can use the rod to direct the spider to the target.

The whole place is filled with traps which you can manually activate by turning the red valves. Use these to sneak by the heavily armed guards and kill them. You have to make your way around the various rooms, killing the guards in the process until you finally reach the main laboratory. You'll also find Calcelmo's nephew, Aicantar in the same area. You can just rush in and kill him and the guard. If you activate the trap, the guard dies but he'll escape, bringing back reinforcements later.

In any case, you can also grab the Dwemer Puzzle Cube to the left of the Enchanter so you can give it to Delvin Later. Open the marked door to exit to the balcony

Exit to the balcony and enter Calcamo's Tower. Once inside, pick up a piece of charcoal and a roll of paper then examine the stone slab to make create a duplicate of the Falmer translating guide.

If you let Aicantar escape earlier, he'll be back with some heavy reinforcements. You can sneak past them or kill them all. (alternately, there is a path on the balcony that leads to a ledge near the waterfall. To avoid going back through the museum, jump. Be cautious though, as a foot to the left or right could mean a swift demise.) Head back to Winterhold and talk to Enthir. You should find him in the Frozen Heart inn cellar, with Karliah.

Listen to Enthir as he translates Gallus' journal. Talk to Enthir, who will offer his assistance as a fence in Winterhold. Talk to Karliah next to complete the mission and get your reward.

Reward: Nightingale Blade



Meet Karliah at the Ragged Flagon

Follow Karliah

Talk to Brynjolf

Infiltrate Mercer's house

(Optional) Speak to Vex about Vald

(Optional) Shoot the mechanism to lower the ramp

Discover the evidence of Mercer's location

Speak to Brynjolf

The shortcut to the Ragged Flagon in the graveyard is locked so you don't have a choice but to take the longer route in the Ratway. Talk to Karliah and follow her to the Cistern. Once there, the other members will confront you and Karliah. Just let them do the talking and watch them discover that their vault has been emptied.

Talk to Brynjolf to update your quest. You have been given permission to kill anybody who stands in your way. Before heading out, you can talk to Vex about Vald as your optional objective. She will tell you that you can talk to Maven about Vald's debt. This is a tedious process so its up to you to just kill the guy (if you're confident and strong enough) or get on his good side.

(Skip this if you just want to kill Vald outright)

Tip:'find the sailboats in Riften dock and Goldenglow Estate swim to the middle of both and then dive straight down

After getting the quill, deliver it to Maven to get the document erasing all of Vald's debts. You can now proceed with the infiltration of Mercer's abode. His house is located conveniently right outside of your guild's alternat exit. You can shoot the mechanism using an arrow for the ramp to go down. This will however, cause Vald to become hostile, thereby killing the chance to speak with him peacefully. You can obtain the house key from him as well.

Continue inside and the deal with the two bandits. Head to the kitchen and find the suspicious cabinet beside the barred door. Open it then open the false back panel to reveal a hidden passage.

Continue through the trap-ridden path until you finally reach the room with Mercer's plans. Grab the valuables here, including the Bust of Gray Fox (for Delvin), some gems inside the bowl and Chillrend. Return to your headquarters after looting the place. Talk to Brynjolf to complete the mission.



Listen to Karliah

Meet Karliah at the standing stone

Follow Karliah

Activate the Armor Stone

Equip the Nightingale Armor

Follow Karliah

Stand on the vacant floor glyph

Speak to Karliah

Speak with Brynjolf


Nightingale Armor Nightingale Boots
Nightingale Gloves
Nightingale Hood

After returning to Brynjolf in the quest The Pursuit you will automatically acquire this quest.

You will be told that Karliah wishes to speak with both you and Bryjolf, she will be in the centre of The Ragged Flagon - Cistern (if not she will head there).

After discussing the course of action regarding Mercer she asks you both to meet her at the The Standing stone, If you have already been there it is called the Nightingale Hall and is directly south of Riften very close to The Shadow Stone. It's best to head there to meet her straight away, as those who take too long to meet her at The Standing stone will be met with a bug in the game that causes her to leave the area, making the quest unfinishable.

Once you meet her at the Standing stone she discusses the Nightingales and takes you into the hall where she hops you and Brynjolf will become Nightingales.

Once inside, activate the armour stone to receive the Nightingale Armour set. These are light armour pieces with some nice enchantments (can be improved with Void Salts). Equip them, then join Karliah and Brynjolf to take the oath in becoming a Nightingale. You can refuse the oath but to continue the quest chain you must become a Nightingale and complete the Oath.

Join the others and stand on the vacant glyph symbol as marked. Nocturnal will speak and accept you as new Nightingales. After completing the Ceremony, Brynjolf will offer you to become the guild leader once everything is finished. The mission will be completed and you'll begin the quest Blindsighted.



Travel to Irkngthand

Speak to Karliah

Locate Mercer Frey

Slay Mercer Fray

Retrieve the Skeleton Key of Nocturnal

Retrieve the Eyes of the Falmer

Escape the Cave

Speak to Karliah


You must traverse three to four levels to find the entrance since this is a rather large ruin to begin with. There is a lever which opens the front gate but its not necessary to use this as you can simply flank to the right as you enter, disable the bear traps on the ground, and ascend the stairs to the second level, third level, etc. You can sneak your way in or just simply walk in and kill them all. The raised gate in the entrance is just a bluff. There's a broken part of the wall where you can enter and work your way around in.

In the first area (Irkngthand Arcanex), fight off a few Dwarven automatons and a fire trap until you reach the lift leading to the Irkngthand Grand Cavern area.

Upon reaching the Grand Cavern, you'll find Brynjolf and Karliah waiting for you. They'll be your temporary followers for the duration of this quest. Continue forth as you'll see Mercer in the other side of the ruins. Continue to the next area where you'll encounter Falmer Shadowmasters. The gate is closed and the only way to open it is to have the two gears rolling. The two levers that will activate the gears are found across each other in the upper level. After activating one, run to the second one immediately since the gears stop automatically after a short while.

On your way, be sure to stop in the room with the Detect Life Scrolls. Mercer Frey uses invisibility spells/scrolls/potions while you're engaged in close combat. Continue to the next large area where you saw Mercer earlier. Kill the falmers, incuding a Dwarven Centurian automaton. Make your way to the path above and it will lead you to the higher ground. Go through the door to reach the Irkngthand Slave Pens.

The Slave Pens is a rather straightforward but narrow area. Fight your way through various enemies until you finally reach the door leading to the Irkngthand Sanctuary.

As soon as you reach the Sanctuary, you'll find Frey already working on removing the Eye of the Falmer. Once you can draw your weapons, attack him. He'll disappear from time to time as part of his tricks. Take note that even if he's invisible, doesn't mean that he's invincible. The obvious shimmer of his movement will still be visible so use this to locate him and attack him when you're in range. You can also find him using the Detect Life spell or scrolls you picked up earlier.

The Skeleton Key of Nocturnal
Left eye of the Falmer
Right eye of the Falmer
Dwarven Sword of Devouring
Imperial Bow of Chills
Leveled Amount of Gold (300)
Potion of Healing


This part is simple if you keep your wits about you:
The room will fill up with water.
Wait until the water is level with the head of the large statue/idol and the head will fall forward--revealing the exit to Bronze Water Cave


Reward: Nightingale Bow



Enter the Twilight Sepulcher

Speak to the Nightingale Sentinel

Follow the Pilgrim's Path

(Optional) Retrieve Nystrom's Journal

Return the Skeleton Key to the Ebonmere

Approach the Nightingale Sentinel (Gallus) and talk to him. After exhausting all inquiries, you'll have the option to search Nystrom's remains nearby for his journal and some other loot.

Once done, go through the tunnel behind him and kill the two hostile Nightingale Sentinels. After that go down the steps and go through the hole behind the fire pit and continue. Descend some more steps, but be mindful of the button on the floor that will release a trap as well as alert the nearby Nightingale Sentinel of your presence. Kill the last evil Nightingale Sentinel and open the door behind it.

In this section, keep yourself in the dark as you go through the room. Exposing yourself to the light will quickly drain your health. You have to be careful of tripwires as well.

When you get through the next set of doors, follow the path down to the statue of Nocturnal and use both chains hidden behind the torches to open the door. Follow the trap-ridden path that will eventually lead you to the door to the inner sanctum, however if you so choose you can open a master skill locked door using your Skeleton Key on the left side of this path before reaching the Inner Sanctum door. There's nothing too special in this room besides a Lock-pick skill book, but you will have to take down two more Sentinels to get it. If not, proceed through the Inner Sanctum door and continue to follow the path again until you reach a well. Jump down the well, and then wait for a few moments and the Skeleton Key will dissolve the floor for you.

Place the key on the slot and Nocturnal herself will appear. Listen to her then talk to Karliah. You now have the choice to become an Agent of Strife, Subterfuge or Stealth. Have Karliah explain the differences between them to know what fits your style.

Half-moon - Subterfuge Crescent - Stealth
Full moon - Strife

After selecting your preferred agent status, take the portal to the entrance.

Andi Hodgetts

Author of Stonehurst