The Elder Scrolls V: Skyrim Thieves Guild Quest Guide: Path to Guild Master

※This article is based on information as of May 27, 2026.
The Elder Scrolls V: Skyrim does not have a seasonal system. The latest major paid content is the "Skyrim Anniversary Edition," which includes numerous Creation Club content items.[23] The latest major free update was released on December 5, 2023, and includes the implementation of the Creations platform, as well as support for Steam Deck and ultrawide monitors.[25]

The "Thieves Guild" makes its name known throughout the shadow world of The Elder Scrolls V: Skyrim. Do not underestimate them as merely a band of thieves. Their headquarters, sprawling beneath Riften, is a stage for adventure, swirling with wealth, fame, and Daedric Prince mystery. This article completely covers the entire questline, from a simple thief to the "Guild Master," the pinnacle of the Guild. From becoming a legendary "Nightingale" and acquiring powerful secret treasures, to the steps for restoring the Guild and amassing vast wealth, we will thoroughly support your career as a thief.

Joining the Thieves Guild and the Main Quest Flow

Everything begins in Riften, the major city of the Rift region. The path to the Guild opens with a deal made with a man encountered in the market. Initially, the focus is on painstaking jobs to restore the Guild's reputation, but the story gradually evolves into a grand conspiracy involving betrayal within the Guild and the Daedric Prince Nocturnal.

Joining Quest "A Chance Arrangement"

To join the Thieves Guild, you must first gain Brynjolf's trust by following these steps:

1. Speak to Brynjolf in Riften's marketplace.
2. Agree to his plan: he asks you to steal Madesi's ring from the market merchant and place it in Brand-Shei's pocket.
3. While Brynjolf distracts everyone in the market, stealthily steal "Madesi's Silver Ring" from the strongbox under Madesi's shop counter.
4. Pickpocket the stolen ring onto Brand-Shei, a Dark Elf also in the market (place it in his pocket while in stealth).
5. Report back to Brynjolf.

• Important Notes: Whether you succeed or fail this quest, you can still proceed to the next quest, "A Cornered Rat," and join the Thieves Guild. However, succeeding will earn you higher regard from Brynjolf. If your Sneak skill is low, it is recommended to save beforehand.

Upon completing this quest, you will be escorted to the Guild's headquarters, "The Ragged Flagon," beneath Riften, officially becoming a member of the Guild. Afterwards, you will undertake quests like "Dampened Spirits" and "Scoundrel's Folly," pursuing the crisis facing the Guild and the traitor behind it.

The Path to "Nightingale," Agent of Nocturnal

The story of the Thieves Guild reaches a major turning point midway. The Guild's true form was "The Nightingales," a secret society serving "Nocturnal," the Daedric Prince of night and darkness. The Dragonborn will become a member of this organization, undertaking an important mission to protect the Daedric Prince's secret treasures.

Quest "Trinity Restored" and Unique Equipment

While pursuing Mercer Frey, the Guild's traitor, the Dragonborn heads with Karliah to the Nightingale Sanctuary. There, a ritual oath to Nocturnal is performed, formally making them a member of The Nightingales.

1. After completing the quest "Pursuit," rendezvous with Karliah and head to the Nightingale Sanctuary south of Riften.
2. Perform the ritual deep within the sanctuary, swearing an oath to Nocturnal.
3. As part of the ritual, you are granted the powerful unique equipment, "Nightingale Armor Set."
4. After the ritual, proceed with Karliah and Brynjolf to Irkngthand to defeat Mercer Frey. During this quest, you can obtain "Nightingale Bow" and "Nightingale Blade."

• Unique Reward: Nightingale Equipment
  The rewards obtained in this quest are very powerful, but be aware that they are "level-dependent equipment," meaning their performance varies depending on the Dragonborn's level at the time of acquisition. To obtain the equipment with the best performance, it is recommended to complete this quest at level 32 or higher.
  • Nightingale Armor Set (Light Armor): Possesses enchantments specialized for stealth actions, such as muffled movement, increased Lockpicking skill, increased Stamina, and increased Frost Resistance.
  • Nightingale Blade (One-Handed Sword): Possesses enchantments for Health Absorb and Stamina Absorb.
  • Nightingale Bow: Possesses enchantments for Frost Damage and Shock Damage.

The Ultimate Pick: "Skeleton Key" and Nocturnal's Powers

During the process of defeating Mercer Frey, the Dragonborn obtains the "Skeleton Key," one of the Daedric Artifacts. This is an unbreakable lockpick, an incredibly powerful item that dramatically reduces the difficulty of Lockpicking.

However, since this key originally belongs to Nocturnal, it must be returned to her during the Thieves Guild main quest "Darkness Returns."

• Keep or Return the Skeleton Key: It is possible to keep the key without returning it, but in that case, the Thieves Guild questline will not be completed, and you cannot become Guild Master. If you return the key, you will be rewarded with the choice of one of three Nightingale powers to use.

Upon returning the key at the Twilight Sepulcher, you will be granted one of the following three powers. This power can be changed once per day by visiting the Twilight Sepulcher:

• Agent of Crescent Moon (三日月のエージェント): A power version of Illusion magic. For 2 minutes, causes enemies and allies to rampage for 30 seconds.
• Agent of Strife (半月のエージェント): A power version of Invisibility. Become invisible for 30 seconds. Taking action breaks the effect.
• Agent of Subterfuge (満月のエージェント): A power version of Absorb. Absorbs 100 points of health from the target.

To the Pinnacle of Glory! How to Become Guild Master

Even after completing the Thieves Guild main quest "Darkness Returns" and resolving issues with Nocturnal, the Guild's complete restoration is not yet finished. To restore the Guild to its former glory and become "Guild Master" yourself, you must re-establish the Guild's influence in each of The Elder Scrolls V: Skyrim's major cities.

Delvin and Vex's "Jobs" and "Special Jobs"

The path to becoming Guild Master is a cumulative effort of diligent work. You will undertake small quests called "Jobs" from Delvin Mallory and Vex in The Ragged Flagon and complete them.

1. Complete the Thieves Guild main questline.
2. Accept "Jobs" such as "Fishing," "Burglary," "Shakedown," "Numbers Job," and "Sweep Job" from Delvin and Vex.
3. Successfully complete 5 jobs in each of the 4 major cities (Whiterun, Windhelm, Markarth, Solitude). (Total of 20 times)
4. Once 5 jobs are completed in a given city, Delvin will assign a "Special Job" to decisively establish influence in that city.
5. Complete all 4 Special Jobs ("The False Front" for Whiterun, "Summerset Shadows" for Windhelm, "Silver Lining" for Markarth, "The Dainty Sload" for Solitude).
6. After completing all Special Jobs, speak to Brynjolf to begin the final quest "Under New Management" and be appointed Guild Master.

• Efficient Approach: The target city for jobs is determined randomly. If you wish to receive jobs for a specific city, it is efficient to "re-roll" by accepting a job for a different city, then immediately speaking to Delvin or Vex to "quit this job" and re-accepting until you get the desired city.

Lavish Rewards for the Guild Master

Upon proudly becoming Guild Master, you will be granted lavish rewards befitting your status.

• Guild Master's Armor Set: A unique light armor set, an improved version of the Thieves Guild leader's armor. It boasts extremely powerful enchantments, including +50 carrying capacity, +35% Lockpicking skill, +35% Pickpocket success chance, and 20% better prices.
• Amulet of Articulation: An incredibly powerful unique accessory that increases Speech skill by 35 points and guarantees success for "Persuade" dialogue options.
• Guild Master's Tribute Chest: A treasure chest that appears near the Guild Master's desk in The Ragged Flagon. It is periodically refilled with gold, gems, and magic items, serving as a continuous source of income.
• Guild Facility Upgrades: The Ragged Flagon becomes more lavish, 4 new merchants are added, and the Guild regains its vibrancy.

Summary

The Thieves Guild questline in The Elder Scrolls V: Skyrim is more than just a story of a group of criminals. It unfolds a grand narrative where you rise through Riften's underworld, eventually becoming the mystical "Nightingale" serving the Daedric Prince Nocturnal, and vanquishing the Guild's traitor. It's packed with replayability elements, such as choices surrounding the ultimate lockpick, the "Skeleton Key," and the diligent work required to become "Guild Master," the pinnacle of the Guild. Numerous powerful unique equipment items and rewards that enhance gameplay are also available. Please use this guide to aim to become the shadow ruler of The Elder Scrolls V: Skyrim.