Thieves Guild Secrets, Tips, and Tricks to Dominate in ‘Skyrim’

If you’re anything like me, you’ve probably spent most of quarantine enjoying your oft-neglected game libraries. For Skyrim lovers, that almost certainly means a replay of 2011’s The Elder Scrolls V: Skyrim. This absolutely massive game has so many character races, storylines and guilds that it is a genuine task to accomplish them all. Some of the more complicated guild quests, in particular, have tripped up newcomers and veteran Skyrim players alike, which brings us to the Thieves Guild.

With all of its backstabbing and intrigue, the Thieves Guild has caused its fair share of confusion over the years. If you are looking to finally polish off this quest line but need a little help along the way, look no further.

The Thieves Guild in Skyrim

To begin, players need to determine if they even want to join the Thieves Guild. Unlike the Dark Brotherhood, there is no option to destroy this wretched hive of scum and villainy. You can, however, restore the former glory of the guild and take the place of its former leader.

The Thieves Guild is, well, exactly what it sounds like. It is where all of Tamriel’s most sticky-fingered residents end up. The enigmatic Mercer Frey leads this guild that has its fingers in many of the businesses scattered around Tamriel. Quests from members of the Thieves Guild will typically see you cooking the books at local businesses, clearing homes of valuables, and even planting stolen goods on various NPCs. You won’t be on the right side of the law as a member, but at least you won’t be slaughtering any innocents à la the Dark Brotherhood.

While the guild’s golden age has passed, there is still a chance to save it. Skyrim players can save the Thieves Guild from collapse by completing the main quests and tracking down the insidious machinations that have lead the guild to the brink.

How to join the guild

To join this shadowy underground (literally) organization, head over to the city of Riften. It is to the far southeast on your map.

Once you’re in Riften, it shouldn’t take you long to run into Brynjolf. Just head to the market during daylight hours, and he should track you down on his own. In order to learn more about the guild, Brynjolf will require a less-than legal task of you. Even if you bungle the initial test, however, you will be granted leave to seek the Thieves Guild’s home base, the Ragged Flagon.

To get there, you’ll first need to traverse the Ratway beneath the streets of Riften. Your first few times will be an exercise in frustration—damn those tunnels can be confusing—but you’ll eventually get a much easier back door into the guild’s headquarters.

You’ll only need to complete one more quest, “Taking care of business,” before you gain membership. This requires players to collect debt that three separate NPCs owe to the Thieves Guild. You can do this through force or a series of careful conversation options. Once you return to Brynjolf and Mercer with news of your success, you’re officially inducted into the Guild.

Don’t attack any member of your new clique, or the wrath of your companions will come down harsh and swift. The Thieves Guild tends to be more forgiving of stealing, but still, proceed with caution.

How to complete Skyrim Thieves Guild quests

There are a number of main quests, as well as radiant quests, available through the Thieves Guild. Radiant quests, which players can obtain through Vex and Delvin Mallory, will provide an unending source of income and experience.

Brynjolf or Mercer assign most main quests, with a few coming through guild associate Maven Black-Briar. By the end of the Thieves Guild quest line, you’ll have learned a lot about your sticky-fingered associates, acquired some armor with excellent stats, and received a choice between several enticing upgrades. You’ll also get your hands on the Skeleton Key, a wonderfully useful tool that, unfortunately, you must relinquish to complete the Thieves Guild quest line.

Return the key to where it belongs and, erm, deal with everything else. Then you’ll be in a position to take over as leader of the Thieves Guild. This title comes with a whole new set of powerful armor and a fantastic speech-related amulet. Just because you’ve completed the main quest, however, doesn’t mean you’re entirely finished with the guild.

Restore the glory of the Thieves Guild

Even after completing the main Thieves Guild quest, players will still have one potential quest to undertake. An achievement titled “Restore the Thieves Guild to its former glory” will remain even after you polish off all but the never-ending radiant quests for Vex and Delvin.

Once you’ve completed the main quest, you’ll need to perform five jobs for Vex and Delvin in four different cities: Markarth, Windhelm, Solitude, and Whiterun. Once you complete five radiant quests in a city, a new quest will be available through Delvin. Complete that quest to “upgrade” the Thieves Guild’s status in that area of Skyrim. Note: Quests in Riften don’t count, so don’t stress over completing them. Once you complete all four cities’ radiant and special quests, the Thieves Guild will finally be back to its former glory. This equals 24 quests in all.

Screw over Maven Black-Briar

This might seem a bit odd, but bear with me. There is a very large contingency of players who enjoy the Thieves Guild quests but hate—absolutely hate—Maven Black-Briar. Unfortunately, given she is a consistent associate of the guild, you’ll have no choice but to work with her.

If her snide comments and pretentious air have you wishing she wasn’t an essential character and could therefore be killed, you’re not alone. Thankfully, hardworking and diligent redditor u/RagnarokHunter has a solution for you. This glorious human, whom commenters dubbed “Bane of Black-Briar,” devised every possible way to screw over the Black-Briar matriarch.

In the very first mission you accomplish for Maven, in which you’re ordered to burn the beehives at Goldenglow Estate, make sure to bungle the job. Burn all the beehives and, though you’ll miss out on pay, you’ll know Maven’s coffers are hurting far more.

While completing the Thieves Guild quest line, you can also chat with Romlyn Dreth, an employee located at his home in the lower part of Riften. He’ll ask you to deliver some Black-Briar mead to an innkeeper. Upon completion, you’ll find that any mead bottles taken from the meadery no longer count as stolen. They sell for a pretty penny, too, especially in large quantities.

Another great way to irritate Maven is through a man named Louis Letrush. You can find him in the Bee and the Barb in Riften. He’ll offer you the chance to complete a deal with Maven’s imprisoned son Sibbi. The job, should you choose to take it, involves stealing a horse from Maven and delivering it to Louis. When you head over to the horse’s location, RagnarokHunter recommends you “kill every Black-Briar mercenary and take everything in the house not bolted down” for good measure. Oh, and you can also keep the horse for yourself. Take that, Maven.

A few additional tips for worsening Maven’s life are sprinkled throughout RagnarokHunter’s post, but they saved the best for last. At “the point in the main quest where you preside a peace council between the Legion and the Stormcloaks,” you want to ensure the Imperials end up with Riften. That will elevate Maven to Jarl. “That way you’ll be able to exile her when you capture Riften for the Stormcloaks.”

Vengeance has never tasted so sweet.

Mods

If you’re aiming to center your next Skyrim play through around the Thieves Guild, it may be worth your while to check out a few mods that are sure to enhance the experience. Anyone who has already played through the quest line at least once will likely enjoy these recommended mods, which alter gameplay just enough to keep things interesting.

Opulent Thieves Guild

This mod is a favorite of Thieves Guild regulars. After the events of the main questline are completed, players will be able to restore the former glory of the Thieves Guild. Once all is said and done, however, the Ragged Flagon doesn’t look all that different. Enter Opulent Thieves Guild.

This mod overhauls the basic changes made to the Thieves Guild headquarters and replaces them with far more decadent alterations. The changes occur gradually, throughout the final steps of the Thieves Guild quest, to add to immersion. By the time you finish, you should have a lavish, somewhat gaudy (but extremely fitting) headquarters for Tamriel’s favorite burglars.

Thieves Guild for Good Guys

It can be hard to pursue many of Skyrim’s factions without getting your hands dirty, and the Thieves Guild is no exception. It may not be quite as bloody as the Brotherhood, but you’ll dole out plenty of death throughout the course of this quest line.

Not to mention the questionable aims, and methods, this faction often opts for. For a much more Robin Hood-esque take on thieving, consider Mordivier2’s creation. This mod allows for far more flexibility to be an altruistic thief, including the ability to give money to the poor and restore the honor of the Thieves Guild by actually helping people. The ability to get rid of Maven at the end is just the cherry on top.

Sneak Tools

There are a number of minor, annoying flaws in the way Skyrim approaches stealth, particularly when it comes to the Thieves Guild. The game is more than 10 years old, though, so I guess it deserves a bit of slack. And thankfully, modder Borgut1337 took the time to create a mod specifically designed to navigate these flaws.

The Sneak Tools mod adds several new features to Skyrim’s sneak system, including the ability to knock out enemies, slit throats, and conceal your identity using masks. None of the additions are intended to alter existing gameplay, but instead serve to enhance any thief characters you might think up.

Skeleton Key

As noted above, you’ll acquire the Skeleton Key near the end of the Thieves Guild questline. This spectacular little tool is an unbreakable lockpick that you can use indefinitely—until you have to return it, that is.

If you choose not to, however, you can keep this key forever. You have the option to keep the key for yourself, rather than return it to the Twilight Sepulcher. The Thieves Guild questline will remain unfinished—a struggle for completionists—but you’ll never need to haul around another lock pick.

Caches

There are a number of Thieves Guild caches hidden throughout Tamriel, but you’ll need a sharp eye to spot them. These caches are always indicated through a shadowmark scratched into the side of a barrel. Thieves Guild barrels are scattered throughout different holds, and at higher levels can contain some serious loot.

Look for the Thieves Guild’s distinct shadowmark outside of Honeyside in Riften, at the base of the waterfall in Markarth, next to Sadri’s Used Wares in Windhelm, and behind the Bannered Mare in Whiterun. A number of others exist—there is even one in Solstheim—so keep a keen eye out.

Best followers

The majority of Thieves Guild quests rely heavily on sneak, which makes sense, given the nature of the guild. These quests can become frustrating, therefore, when you are accompanied by a follower lacking in sneak skill. There are several things that can be done to offset a noisy character, such as outfitting them in light armor enchanted with muffle and sneak skills, but ultimately some followers are far less fitting for this storyline than others. If you’re looking for the best possible Thieves Guild experience, consider one of these followers.

Jenassa

Jenassa is a Dunmer mercenary you can find lounging at the Drunken Huntsmen in Whiterun. She can be hired for the typical 500 gold, and is an excellent stealth companion—so long as your character is a relatively low level.

Jenassa maxes out at level 40, at which point you’ll want to retire her for a more powerful option. Otherwise, you’ll continue to improve while she gradually drags you down. Thankfully, she is available for marriage, so you won’t have to say goodbye forever.

Aela the Huntress

One of the more prominent members of the Companions, this Nord fighter is high in sneak as well as light armor and one-handed. She is also a specialist in archery, which she is available to teach, and she’ll offer your character lycanthropy mid-way through the Companions’ questline.

You’ll find Aela in Jorrvaskr, located in Whiterun. She will agree to become a follower once you’ve completed the Companions’ main questline. Like Jenassa, she will also eventually become available as a marriage option.

Cicero

He may be one of the more obnoxious Skyrim follower options, but honestly Cicero makes an excellent companion. His high levels in sneak and one-handed make him an perfect choice for anyone looking to go unnoticed, but he does bust the occasional dance move, so be wary.

Cicero can be found on the road north of Whiterun early in the game, and after that at the Dark Brotherhood Sanctuary near Falkreath. He will become available as a follower once the quest “Hail Sithis!” has been completed.

Dark Brotherhood Initiate

This entry technically offers two follower options, but given they have the same stats and perks, I’m counting them as one and the same. Either a male or female Dark Brotherhood Initiate can be gained as a follower after you speak to Delvin Mallory about repairs to the Dawnstar Sanctuary. The next time you make a trip to the northern base, they should be waiting for you.

These characters are some of the best followers Skyrim has to offer. They are sneaky and boast high health, plus they level up past 50 with your character. The initiates are also considered essential, and can be stacked with another follower to ensure an easy victory in your next fight.

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