You’re standing in the middle of a literal sewer, breathing in the stench of Riften’s "Ratway," and some guy named Brynjolf tells you that you haven’t earned a coin in your life. It’s insulting. It’s also the perfect hook. Most players start the Skyrim Thieves Guild questline because they want the Skeleton Key or that sweet Nightingale armor, but honestly, if you pay attention, this is the most depressing story arc in the entire game.
It isn’t just about stealing stuff.
The guild is dying when you find them. They’re cursed. Their luck has run dry, and they’re basically a group of homeless thugs living in a basement while Maven Black-Briar holds their leash. You aren't joining a glorious brotherhood of shadows; you're joining a sinking ship.
How to actually start the Skyrim Thieves Guild questline without breaking your game
Look, most people just walk into the Riften market and talk to Brynjolf during the day. He gives you a quest called "A Chance Arrangement" where you have to plant Madesi’s ring on Brand-Shei. It’s simple, but here’s the thing: you can actually fail this on purpose and still get into the guild. If you get caught or lose the ring, Brynjolf basically says, "Well, you suck, but we're desperate."
That tells you everything you need to know about their state of affairs.
Once you’re in, you head down to the Ragged Flagon. It’s a pub in a hole. You meet Mercer Frey, the Guild Master who looks like he hasn't slept since the Second Era. He’s grumpy, dismissive, and clearly hiding something. Your first real job is "Taking Care of Business," where you shake down a few local shopkeepers. It feels dirty because it is. You aren't Robin Hood. You’re the muscle for a local mafia that’s fallen on hard times. Keerava, Bersi, and Haelga—they all have leverage points. Smash a vase, threaten a family, or steal a statue. Do whatever works.
The shift from petty crime to Daedric conspiracies
Everything changes once you hit the Goldenglow Estate mission. This is where the Skyrim Thieves Guild questline stops being about "protection money" and starts being about a massive betrayal. You find out someone is actively trying to destroy the guild from the inside.
Then comes Karliah.
The game frames her as the villain initially. Mercer tells you she killed the previous Guild Master, Gallus. But when you finally corner her in Snow Veil Sanctum, the rug gets pulled out from under you. Mercer stabs you—yes, the Dragonborn gets shanked in a cutscene—and you realize the guy leading the guild is the one who’s been looting the vault. It's a classic noir twist. Karliah isn't the murderer; she’s the scapegoat.
💡 You might also like: Why Metal Sonic CD Voice is Still the Weirdest Mystery in the Series
Becoming a Nightingale: The price of power
To beat Mercer, you have to become a Nightingale. This is the part of the questline where the lore gets heavy. You aren't just a thief anymore; you're a servant of Nocturnal, the Daedric Prince of Luck and Darkness.
A lot of players miss the weight of this.
By taking the oath, you are literally selling your soul. In the afterlife, you don't go to Sovngarde. You go to the Evergloam to guard the Twilight Sepulcher for eternity. Brynjolf and Karliah just sort of shrug and say it’s part of the job. It’s a massive commitment for a cool set of leather armor and some powers that you’ll probably forget to use half the time. But the armor is legendary. It has that distinctive cape and the face mask that makes you look like a fantasy Batman.
The showdown with Mercer Frey in Irkngthand is one of the most mechanically interesting fights in Skyrim. The room floods. You’re fighting a master thief who can turn invisible. If you don't have a way to detect life or some decent AOE spells, he can be a real pain on higher difficulties. Once he's dead, you get the Skeleton Key—the best item in the game that you should absolutely never give back until you've leveled your Lockpicking to 100.
Restoring the glory: The grind nobody talks about
Here is where most players quit. They kill Mercer, they return the Skeleton Key, they become the Guild Master, and they think they're done.
Wrong.
The Skyrim Thieves Guild questline isn't actually finished until you restore the guild to its former influence. This requires doing "small jobs" for Delvin and Vex. You need to complete five jobs in each of the major holds: Whiterun, Markarth, Windhelm, and Solitude.
It is a slog. It is repetitive. It's honestly kind of annoying.
But as you complete these regional influence quests, the Ragged Flagon actually changes. New merchants move in. The dirt and grime get cleared away. You start seeing guild banners flying. You get the Guild Master’s Armor, which has a massive carry weight bonus, and the Tribute Chest appears in the master's desk. This chest refills with loot periodically, giving you a passive income.
Common misconceptions and bugs to watch out for
Don't ignore the "Larceny Targets." These are unique items you find during the main quests—like the Queen Bee Statue or the Honningbrew Decanter. You can sell them back to Delvin for a decent chunk of gold, and he displays them on the shelf behind the leader's desk. If you miss them during the quest, some of them are incredibly hard to go back and get because the cells might lock or change.
Also, watch out for the Brynjolf bug. Sometimes he’ll just keep saying "I'm busy" even after the questline is done. This usually happens if you didn't finish the influence quests properly or if you have certain mods that mess with NPC packages. To fix it, you usually have to force the next stage of the quest via console commands on PC, or just keep doing Vex's jobs until the game realizes you're the boss now.
The questline is a bit controversial among hardcore RPG fans. In previous games like Oblivion, the Thieves Guild had a "Grey Fox" Robin Hood vibe. In Skyrim, they're more like a fallen organized crime family. Some people hate that. They think it's too dark or that the Daedric Nightingale stuff feels out of place. Personally? I think it adds stakes. It makes the world feel older and more dangerous. You aren't just picking pockets; you're dealing with cosmic forces of luck and misfortune.
Practical steps for your next playthrough
If you're jumping back into Riften, do it with a plan. Don't just rush the main story.
First, grab the Thief Stone near Riverwood for that 20% skill increase. It makes the early lockpicking and pickpocketing grinds much less painful. Second, keep the Skeleton Key for as long as possible. Seriously. There is no penalty for holding onto it for 50 hours while you go clear out every ancient tomb in Skyrim.
Third, and this is important for your sanity: when doing the influence jobs for Delvin and Vex, you can quit a job if it's in a city you've already completed. If Vex gives you a job in Whiterun and you've already done five there, just tell her you want to quit and take a new one. It doesn't hurt your reputation.
Lastly, focus on the "Bedlam" and "Sweep" jobs. They're usually the fastest to complete and get you back to the Flagon quickly. Once you’ve restored the guild, you’ll have access to fences with 4,000 gold each, which is basically the only way to sell high-level loot without waiting 48 hours for a merchant to reset.
👉 See also: Ghost of Tsushima Lethal Mode: Why It’s Actually Easier (And More Brutal) Than Hard
The Thieves Guild isn't just a questline; it's a long-term investment in your character's economy. Get in, get the armor, sell your soul to a shadow goddess, and make sure Mercer Frey dies in that flooded ruin. It’s the Skyrim way.