Skyrim Thieves Guild Questline Guide: Rewards and Choices

The Thieves Guild line is the one faction quest chain in Skyrim where the rewards actually keep paying out after the credits roll. You start as a nobody who gets framed for pickpocketing in Riften, and you end it running the whole outfit, with better fences than any other merchant in the game and some of the strongest light armor you can find. The catch is that "finishing" the story and actually rebuilding the guild are two different jobs, and a few choices along the way (which blessing you take, when you claim your gear, whether you pay off a certain debt) change what you walk away with. Here's the whole run, start to Guild Master.

Joining the Guild in Riften

Finding Brynjolf

There's no level requirement and no skill check to start. Walk into Riften and Brynjolf will more or less find you. He works the market stalls during the day and drinks at the Bee and Barb at night, and either way he'll pitch you a little scheme once he spots you. You can't miss him, and honestly you can't fully avoid him either (his opening quest tends to land in your journal even if you ignore the guild entirely).

A Chance Arrangement

The first job is small: frame Brand-Shei, the Dunmer trader at the market, by planting a stolen ring on him. The ring is Madesi's Silver Ring, and it sits in a strongbox inside a locked cabinet under Madesi's stall counter. Both are locked, so either pick the two locks at night before the hustle starts or lift the key straight off Madesi's belt. Once Brynjolf starts hawking his "Falmer blood elixir" and the crowd gathers round, grab the ring, sneak behind the crates Brand-Shei sits on, and slip it into his pockets.

Two nice touches here. The game quietly gives you a hidden perk that boosts pickpocket chance by 30% for the duration, so the plant is much safer than it looks. And if you'd rather not send an innocent man to jail, you can drop the ring instead and tell Brynjolf you lost it. He grumbles, Brand-Shei stays free, and the quest moves on exactly the same. Pay for the job is 100 septims either way, and even getting caught doesn't lock you out, you just get to watch Brynjolf shrug it off.

Taking Care of Business

Next he points you at the Ratway, the tunnel network under the city, and the Ragged Flagon tavern at the bottom of it. The walk down has a couple of lowlifes and a brawler named Gian the Fist (his Gloves of the Pugilist are worth grabbing for unarmed builds), and once you reach the Flagon the real quest starts: collect debts from three shopowners, 100 gold apiece.

Each one has a soft option if you'd rather not throw fists:

• Keerava (Bee and Barb innkeeper) - talk to Talen-Jei, her partner, first. He reveals her family lives on a farm just inside Morrowind, and mentioning that you know about it scares the payment out of her without a fight.
• Bersi Honey-Hand (Pawned Prawn) - he refuses until breakables enter the picture. Smash his prized Dwemer urn and he folds on the spot. Just know the urn stays broken forever.
• Haelga (Bunkhouse) - swipe the golden Dibella statue from the drawers around the corner, then threaten to drop it down a well. She pays up fast.

Whoever you leave for last caves immediately, having heard what you did to the others. Keep all three alive and Brynjolf slips you a bonus of three potions on top of the deal. From here you're a member: Tonilia hands you the Thieves Guild armor set (the chest piece adds 20 carrying capacity), and a back entrance through the Riften graveyard opens up so you never have to slog the Ratway again. One warning for the whole questline, the guild expels you for killing anyone on a job or robbing your own, and buying your way back in costs 1,000 gold.

Key Jobs and Fences

The job board

After Taking Care of Business, Delvin and Vex in the Flagon become an endless job board, one active gig each at a time:

• Delvin runs the Numbers Job (fudge a shop's ledger), the Fishing Job (pickpocket a specific item), and the Bedlam Job (steal 500 gold worth of loot from a hold without a single witness).
• Vex runs the Burglary, Shill, Sweep, and Heist jobs, all variations on "sneak into a home or shop, lift the thing, don't get caught."

Pay is leveled and identical across the job types: 50 gold at levels 1-5, climbing through 100, 150, 200, 250, 300, 350 and 400 to 500 gold at level 42+. The real payout is the stolen goods themselves, which you keep and can fence, plus the progress toward restoring the guild (more on that below). Two rules get jobs failed: getting jailed, or killing anyone who lives at the target. Getting seen mid-theft voids Bedlam progress too. Quitting a job costs you nothing, which matters because you can accept, quit, and re-ask until you land a job in the city you're working on.

Fences are the whole point

Fences buy stolen goods and strip the stolen tag off them, and most merchants in Skyrim simply won't. Tonilia is your first, available the moment you join. The rest open up as you play:

| Fence | Where | What opens them | | --- | --- | --- | | Tonilia | Ragged Flagon, Riften | Joining the guild | | Mallus Maccius | Honningbrew Meadery | Dampened Spirits | | Gulum-Ei | The Winking Skeever, Solitude | Scoundrel's Folly | | Enthir | College of Winterhold | Hard Answers | | Endon | Markarth | Silver Lining | | Niranye | Windhelm | Summerset Shadows | | Atahbah, Ma'jhad, Zaynabi | Khajiit caravans | Moon sugar delivery for Ri'saad |

Guild fences start with 1,000 gold to trade against, which already beats regular merchants. Finish all four city reputation quests and that pool grows to 4,000 gold, the fattest merchant wallets in the base game (Enthir's the exception, his stays at 500). Tonilia also occasionally stocks Daedric weapons, which is a cheap way to get one early.

Restoring the four cities

The guild's revival runs on those small jobs. Complete five jobs in a single hold's capital (Markarth, Solitude, Whiterun, or Windhelm; the Rift already belongs to the guild) and Delvin hands you a special reputation quest for that city: Imitation Amnesty in Whiterun, Silver Lining in the Reach, Summerset Shadows in Eastmarch, and The Dainty Sload in Haafingar.

Each one you finish fixes up the Ragged Flagon a bit and moves a new merchant in: Syndus the fletcher after one, apothecary Herluin Lothaire after two, blacksmith Arnskar Ember-Master after three, and a second blacksmith, Vanryth Gatharian, after all four. You also gain the ability to bribe guards in that hold to make bounties vanish, no Speech perk needed, and without your stolen goods getting confiscated. Practical tip from everyone who's done this grind: the Reach gets fewer random job assignments than the other holds, so any job that lands in Markarth is worth taking on the spot.

Larceny loot for Delvin

Scattered through the story dungeons are seven collectibles Delvin pays extra for: the Queen Bee Statue at Goldenglow Estate, the Honningbrew Decanter, the East Empire Shipping Map, the Model Ship in Snow Veil Catacombs, the Dwemer Puzzle Cube in Calcelmo's Laboratory, the Bust of the Gray Fox at Riftweald Manor, and the Left Eye of the Falmer from Irkngthand. Selling them to Delvin displays the set on the shelves behind the Guild Master's desk and completes The Litany of Larceny. They're easy to miss in the moment, so keep an eye out as you run each quest.

Nightingale Hall Requirements

What it takes to get in

There's no level gate and no skill requirement. Nightingale Hall opens purely through the story: finish The Pursuit, and Karliah asks you and Brynjolf to meet her at the Shadow Stone just outside Riften's southwest gate, which leads into the Hall. The quest itself suggests fairly modest levels (Darkness Returns is tuned around level 8, Blindsighted around 12), but the real requirement is just patience, since it sits nine quests deep in the chain.

The oath

Inside, Karliah walks you to an armor stone that hands you the full Nightingale set, and you have to equip it to keep the quest moving (you can swap back to your own gear the second the scene ends). Then comes the part with teeth: the oath. To progress, you swear yourself to Nocturnal as one of her Nightingales, and there is no way through the questline without it. Service in life, guarding her stuff after you drop dead. Karliah, Gallus, and Mercer were the old trinity, and with Gallus murdered and Mercer gone rotten, you and Brynjolf fill the empty spots.

After the questline wraps up, the Hall turns into a proper home base with a bed, and Karliah settles in there. It's quiet, out of the way, and nobody bothers you.

Don't claim the gear too early

Here's the gotcha most players learn the hard way. Nightingale gear is a leveled item, and the version you get is locked to your level the moment you start Trinity Restored, not when you actually wear it. The chest piece jumps from +20 stamina and 15% frost resist (levels 1-18) to +30 and 30% (19-31) to the full +40 stamina and 50% frost resist at 32+. The Nightingale Blade from Hard Answers and the Nightingale Bow from Blindsighted lock in the same way when each quest pays out. If you're min-maxing, the move is to stall the last few story quests, level to the mid-30s or beyond, then cash in. If you're playing normally, just know a level 15 set will feel dated by level 40, and there's no upgrade path later.

Karliah and Mercer Frey

The double cross at Snow Veil

For most of the chain, the guild believes Karliah murdered the old Guild Master, Gallus, and vanished. So Speaking With Silence sends you hunting her through Snow Veil Sanctum northeast of Windhelm with Mercer Frey at your side. He's smug, he opens locked doors that "should be impossible," and the deeper you go the worse it feels. In the final chamber Karliah shoots you with a paralytic arrow before you can act, and while you lie frozen the two of them talk: Mercer killed Gallus twenty-five years back and pinned it on her. He then stabs your paralyzed body and walks off.

You wake up outside, alive, because Karliah's arrow was a trick, the poison slowed your heart and kept you from bleeding out. She was aiming for Mercer, took the split-second option instead, and now she needs you to clear her name. As story twists go, it's one of Skyrim's better ones, and it reframes everything the guild thought it knew.

Hard Answers

Proof lives in Gallus's encoded journal, which Karliah hands over. Getting it read is the quest: Enthir at the College of Winterhold can translate it, but the journal is written in Falmer, so you end up sneaking into Calcelmo's Laboratory in the Markarth museum to copy the Falmer script off his stone. That lab also hides the Dwemer Puzzle Cube for Delvin's larceny shelf. When the dust settles, the journal confirms everything, and Karliah gives you Gallus's sword, the Nightingale Blade, which absorbs health and stamina with every swing.

The Pursuit and Vald

Back at the Flagon, the vault gets opened and found completely empty, Mercer robbed his own guild on the way out. The trail leads to Riftweald Manor, his house in Riften, which is guarded by Vald, Maven Black-Briar's hired muscle. You've got real options here:

• Clear his debt - the clean route. Do the Vald's Debt side job, fetch the Quill of Gemination, hand it over to Maven, and Vald hands you the key and stands down gratefully.
• Persuade him - a hard Speech check ("Mercer needs you in Markarth") gets the key with zero gold spent.
• Kill or trick him - outright murder works but feels grim, or shoot the ramp mechanism in the yard, then kite him to the guards and let them do it.

You can also skip Vald entirely by climbing the Temple of Mara's roof and Whirlwind Sprinting onto the balcony. Inside, past the trapped tunnels, Mercer's office holds his plans, the Bust of the Gray Fox for Delvin, and Chillrend in an expert-locked display case. Grab that sword. At its top level it deals 15 base damage plus 30 frost and a 2-second paralyze, which is absurd for a one-hander.

Blindsighted

The finale runs through Irkngthand, a big Dwemer ruin crawling with Falmer and spinning machines, down to the great Falmer statue where Mercer is prying out the Eyes of the Falmer. The fight has two tricks. First, he hits Brynjolf with an Agent of Subterfuge effect, so your own allies spend the battle trying to kill Karliah while you duel him alone. Second, he turns invisible on and off. Grab the Detect Life scrolls lying in the room just before the sanctuary (or use Aura Whisper) and he stops being a problem. Stand on the stairs and he'll come to you instead of backstabbing.

When he drops, the room floods. Loot his body fast, the Skeleton Key and both Eyes of the Falmer are on him, then swim up and out through the hole that opens above the statue. Karliah meets you outside and gives you her Nightingale Bow, which lands frost, shock, and a slow in one shot.

Best Rewards to Claim

The Nightingale set

At the level 32+ tier, the set looks like this:

| Piece | Armor | Weight | Enchantment | | --- | --- | --- | --- | | Nightingale Armor | 34 | 12 | +40 stamina, 50% frost resist | | Nightingale Hood | 15 | 2 | Illusion spells cost 17% less | | Nightingale Gloves | 10 | 2 | Lockpicking 25% easier, +25% one-handed damage | | Nightingale Boots | 10 | 2 | Muffled, you move silently |

Wearing all four adds a 25-point armor bonus on top of the listed ratings. It's excellent thief kit, the muffled boots alone justify it for any sneak build, and tempering each piece just takes void salts plus the Arcane Blacksmith perk.

The Skeleton Key and Nocturnal's gift

Between Blindsighted and Darkness Returns you're holding the Skeleton Key, a lockpick that never breaks. This is the one big self-serving choice in the questline: you can sit on it indefinitely and never finish Darkness Returns, keeping a master-tier lockpick in your pocket for the rest of the game. Plenty of players do exactly that. The cost is that the quest sits open forever, and you can't become Guild Master with it unfinished, so it's a decision between convenience now and closure later.

Hand the Key back at the Twilight Sepulcher (walk the Pilgrim's Path, stick to the shadows in the light room, pull both chains at the statue) and Nocturnal lets you pick one of three agent powers:

• Agent of Shadow (crescent moon) - invisible for 2 minutes while sneaking. The lazy good one, works for basically every build that crouches.
• Agent of Subterfuge (half moon) - nearby enemies turn on each other for 30 seconds. Chaos, very funny in bandit camps.
• Agent of Strife (full moon) - a tether that drains the target's life into yours.

Powers are once a day, and you're not married to your pick, you can return to the Ebonmere and step on a different circle, just no more than one change per day.

The Guild Master's kit

The big prize. Complete Darkness Returns plus all four city reputation quests and Under New Management fires: a ceremony in the Cistern, then Brynjolf hands you the Tribute Chest Key and the Amulet of Articulation, and Tonilia trades your old guild armor for the Guild Master's set:

| Piece | Armor | Enchantment | | --- | --- | --- | | Guild Master's Armor | 38 | Carrying capacity +50 | | Guild Master's Hood | 16 | Prices 20% better | | Guild Master's Gloves | 11 | Lockpicking 35% easier | | Guild Master's Boots | 11 | Pickpocketing 35% better |

That's a stronger set of stealth enchantments than the base Nightingale gear, and unlike the Nightingale stuff it isn't level-locked. The Amulet of Articulation is the sneaky-good piece, persuasion checks almost always succeed while you wear it, and it makes your Speech 35% better, which shows up in every price you're quoted. Between the amulet and the hood you're functionally wearing a haggling suit. One caution from the wiki bugs list: don't sell off your original Thieves Guild armor before this point, Tonilia needs it for the trade-in (there are spare pieces in the Cistern training room if you already did).

Smaller perks worth grabbing

A few things people sleep on. The Cistern has master trainers for Lockpicking (Vex), Sneak (Delvin), Archery (Niruin), and Pickpocket (Vipir the Fleet), so you can dump money into your thief skills at home. Thieves caches start spawning in restored cities, free loot barrels for members. Roadside thieves stop robbing you and start paying tribute once you're far enough along. And the tribute chest next to the Guild Master's desk fills with gold, gems, and potions over time, so swing by and empty it whenever you're in Riften. It's not huge money, but it's free, and it keeps trickling in for the rest of the game.