The Thieves Guild you join in Riften is a mess. Members are leaving, the Ragged Flagon is half empty, and the guild’s luck has run out so completely that even the thieves blame a curse. Your job is to fix all of it, and the game never really explains that fixing it is two separate jobs.
Here’s the thing most guides won’t tell you: finishing the story does not make you Guild Master. You also have to rebuild the guild’s influence in four cities. This guide covers both, in order, with the fastest way through the grind.
How to Join the Thieves Guild
Walk around Riften’s market in daytime and Brynjolf will approach you with a “harmless” plan to frame a merchant. That is A Chance Arrangement. Pull it off and he invites you to the Ragged Flagon, the guild’s tavern deep in the Ratway beneath the city. You get in through the Ratway entrance by the canal or, later, the secret cistern entrance in Riften’s graveyard.
Your second quest, Taking Care of Business, has you collect three debts in Riften. Finish it and you are a member, with access to Delvin Mallory and Vex for side jobs.
Thieves Guild Questline in Order
| Quest | What you do |
|---|---|
| A Chance Arrangement | Steal a ring and plant it on a market trader for Brynjolf. |
| Taking Care of Business | Collect three debts in Riften to prove yourself. |
| Loud and Clear | Raid Goldenglow Estate outside Riften and burn its beehives. |
| Dampened Spirits | Sabotage the Honningbrew Meadery near Whiterun for Maven Black-Briar. |
| Scoundrel’s Folly | Lean on the Argonian informant Gulum-Ei in Solitude. |
| Speaking With Silence | Track down the Dunmer behind the guild’s troubles. |
| Hard Answers | Get Gallus’s journal translated in Markarth. |
| The Pursuit | Search Riftweald Manor in Riften for clues. |
| Trinity Restored | Become a Nightingale, one of Nocturnal’s guardians. |
| Blindsighted | Chase the traitor into a Dwemer ruin and stop him. |
| Darkness Returns | Walk the Pilgrim’s Path in the Twilight Sepulcher and return the Skeleton Key. |
| Under New Management | Take over as Guild Master once all four cities are restored. |
Lore Drop: the guild’s “bad luck” is not a figure of speech. Its fortune is tied to Nocturnal, the Daedric Prince of night and luck, and to an artifact that went missing. Lore nerds, this one’s for you: Darkness Returns is where the curse finally gets explained, and the Twilight Sepulcher is one of the most atmospheric dungeons in the game.
Nightingale Powers
Trinity Restored makes you a Nightingale and gives you the Nightingale armor, blade and bow, which scale with your level when you receive them. After Darkness Returns you can choose one of three powers at the Nightingale stone in Nightingale Hall, and swap later:
- Agent of Stealth: Shadowcloak of Nocturnal, which turns you invisible while you sneak.
- Agent of Subterfuge: turns enemies against each other.
- Agent of Strife: drains health from your target and gives it to you.
If you are building around sneaking, this whole questline slots perfectly into a stealth archer build.
How to Restore the Thieves Guild
Restoration runs on the radiant jobs from Delvin Mallory and Vex. You can hold one job from each at the same time.
- Delvin’s jobs: alter a store ledger (Numbers), lift something from a pocket (Fishing) or steal a set value of goods (Bedlam).
- Vex’s jobs: steal a special item from a wealthy home, plant evidence, steal three valuables or take one item from a shop.
- The rule: five jobs in a city unlock that city’s special influence quest from Delvin.
- The cities: Whiterun, Markarth, Windhelm and Solitude. Riften does not count; it is already guild territory.
| City | Influence quest | What it unlocks |
|---|---|---|
| Whiterun | Imitation Amnesty | Bounty reduction in Whiterun |
| Markarth | Silver Lining | Endon as a fence |
| Windhelm | Summerset Shadows | Niranye as a fence |
| Solitude | The Dainty Sload | Bounty reduction in Solitude |
Each influence quest also adds a new merchant to the Ragged Flagon and lets guild fences carry more gold. The Math: four cities times five jobs is 20 radiant jobs, plus four influence quests, before Under New Management can start.
Tips to Speed Up the Grind
- Take both jobs at once: one from Delvin, one from Vex. If both land in the same city, you finish twice as fast.
- Watch out for Fishing and Bedlam: these can send you outside the four cities, and those jobs do not count toward any city’s five.
- Check your quest journal: it tracks how many jobs you have done per city.
- Stay focused: jobs are assigned at random, so you will sometimes get a city you have already finished. Do them quickly or take the next one.
Actually Do This: start the radiant jobs as soon as Taking Care of Business is done. By the time the main story wraps up, you will already have most cities half finished.
Rewards for Becoming Guild Master
- Guild Master’s armor: a stronger version of the guild armor set.
- Amulet of Articulation: boosts Speech and makes persuasion much easier.
- Better fences: guild fences carry up to 4,000 gold, or 5,000 with the Master Trader perk.
- Bounty protection: guild influence lowers bounties in restored cities.
Thieves Guild FAQ
How do you start the Thieves Guild questline?
Walk around Riften’s market during the day until Brynjolf talks to you. His job, A Chance Arrangement, starts the questline.
How many jobs does it take to restore the Thieves Guild?
Five radiant jobs in each of Whiterun, Markarth, Windhelm and Solitude, plus each city’s influence quest. That is 20 jobs and four special quests.
Can you become Guild Master without restoring the guild?
No. Under New Management only starts after the main story and all four city influence quests are done.
What are the Nightingale powers?
Agent of Stealth, Agent of Subterfuge and Agent of Strife. You pick one at the Nightingale stone after Darkness Returns and can swap later.
The Thieves Guild is one of Skyrim’s most replayed questlines, and our Skyrim Special Edition player stats show plenty of people still sneaking around Riften. For the choice of race and build behind your thief, start with our best overall build and browse the rest on our Skyrim hub.
