If you’ve spent any time roaming the Rift’s foggy alleys or sneaking through Riften’s market stalls picking pockets, you’ve probably heard hushed whispers about the Nightingales. This shadowy, Nocturnal-worshipping faction is tied directly to the Thieves Guild’s deepest secrets, and learning how to join the Nightingale in Skyrim is one of the most rewarding side quests for stealth-focused players. I’ve run this questline at least a dozen times across different playthroughs, and I’ve put together this guide to help you avoid the common mistakes that trip up new players, no matter your build or play style. You don’t need to be a master sneak to pull this off, either—there are workarounds for almost every tricky part if you know where to look.
Prerequisites You Need to Meet Before You Can Join the Nightingale in Skyrim
You can’t just show up at Nightingale Hall and ask to sign up, no matter how good your sneaking skills are. The faction is locked behind the core Thieves Guild questline, and you’ll need to complete a specific set of tasks before you get the invitation to join. I made this mistake on my first playthrough, I spent an hour trying to pick the lock on the Nightingale Hall entrance west of Riften and got nowhere, so save yourself the time and work through the guild quests first.
To unlock the Nightingale initiation quest, you’ll need to hit these three key milestones first:
- Complete the first 7 core Thieves Guild quests, from "A Cornered Rat" up to "Blindsighted"
- Reach at least level 10 to handle the combat encounters in the final lead-up quests
- Have at least 20 points in Sneak to make the stealth sections far less frustrating (though not strictly required)
You do not need to complete all the extra Thieves Guild side jobs from Delvin and Vex to unlock the Nightingale questline. That’s one of the most pervasive myths about this faction, and I’ve seen dozens of players grind through dozens of boring fetch quests unnecessarily because they thought they had to. The extra jobs are only required if you want to fully restore the Thieves Guild to its former glory and get the guild master armor, but they don’t impact your ability to join the Nightingales. If you get stuck on the "Blindsighted" quest, bring a fire-enchanted weapon to take down the Falmer bosses quickly—they’re incredibly weak to fire damage, and this will cut your quest time in half.
What to Expect During the Nightingale Initiation Quest
Once you finish "Blindsighted", Brynjolf will reach out to you and ask you to meet him and Karliah at Nightingale Hall, and that’s where the initiation officially starts. The quest is called "Trinity Restored", and it walks you through the history of the Nightingales, their oath to Nocturnal, and the responsibilities that come with being a member of the faction. You don’t have to make any tough choices during the first half of the quest, but you will want to pay attention to the dialogue if you care about Elder Scrolls lore.
The only slightly tricky part of the initiation is the shadow path trial, where you have to walk across a narrow, invisible path over a deep chasm. Don’t overcomplicate this part—just follow the glowing blue runes on the ground, and move slowly. If you fall off, you won’t die immediately, but you will have to fight a handful of weak skeletons before you can climb back up and try again. I usually just save right before I start the path so I can reload quickly if I mess up.
There is no way to reverse the Nightingale oath once you take it, so be sure you want to commit to the faction before you finish the quest. That doesn’t mean you can’t join other factions later, of course—you can still be a member of the Companions, the College of Winterhold, and even the Dark Brotherhood at the same time with no in-game penalties. It just means you’ll always be marked as a Nightingale in your quest log, and you can’t undo the ritual if you decide later you don’t want to be associated with the faction. The Nightingale armor you get during initiation is leveled, so if you wait until level 30 or higher to complete the quest, you’ll get the maximum stat version of the set. I usually hold off on finishing the initiation until I hit level 30 on my stealth playthroughs for that exact reason.
Perks and Rewards You Get After Joining the Nightingales
The rewards for joining the Nightingales are easily some of the best in the game for stealth builds, and they’re more than worth the time you’ll put in working through the Thieves Guild questline. Once you join the Nightingale in Skyrim, you’ll also get access to exclusive dialogue options with Thieves Guild members, who will treat you with far more respect than they did when you first showed up in Riften as a random stranger.
The first and most obvious reward is the full Nightingale armor set, a light armor set that comes with fortify Sneak, fortify Lockpicking, fortify Illusion, and Muffled Movement enchantments. If you have the Arcane Blacksmith perk, you can upgrade the set with ebony ingots to make it even stronger, and it will stay viable all the way to max level. The set also has that iconic black and blue design that looks way cooler than most other light armor sets in the game, so it’s a great pick for roleplay runs too.
You’ll also get the Nightingale Bow, a unique bow that deals frost damage and absorbs 15 points of stamina per hit, which is perfect for sneaky archer builds who don’t want to run out of stamina mid-fight. You’ll also unlock three unique Nightingale powers that you can use once per day: Shadowcloak of Nocturnal, which makes you invisible for 2 minutes when you crouch, Nocturnal's Strife, which absorbs 100 points of health from an enemy, and Nocturnal's Luck, which gives you a huge boost to your pickpocket and lockpicking success rates for 2 minutes. You can swap between these powers anytime by visiting the Twilight Sepulcher, so you don’t have to stick with one forever.
The Nightingale's lockpicking bonus stacks with other fortify lockpicking enchantments, letting you open master-level locks without any points in the lockpicking skill if you build right. I’ve used this trick on my warrior playthroughs to get through locked doors without wasting lockpicks, and it works every time. You’ll also get access to a safe, non-respawning storage chest in Nightingale Hall where you can store all your stolen goods without worrying about them disappearing or being confiscated if you get arrested.
Common Mistakes to Avoid When Joining the Nightingales
Even if you follow all the steps, there are a few common mistakes that can ruin your run or make the quest way harder than it needs to be. The first mistake I see new players make all the time is finishing the initiation quest too early, before they hit level 30, so they get a weak, low-level version of the Nightingale armor that becomes obsolete after a few levels. If you’re already halfway through the initiation and realize you’re too low level, you can just leave Nightingale Hall and come back later when you’ve leveled up more—the quest won’t fail.
Another big mistake is killing any of the core Thieves Guild members before you start the initiation quest. If you kill Brynjolf, Karliah, or any of the other key guild members, the Nightingale questline will fail permanently, and you’ll never be able to join the faction. If you accidentally attack a guild member, just yield immediately and pay the small bounty to fix the issue before it escalates. I once stole Karliah’s dagger on a playthrough just to test it, and I had to pay 1000 gold to Brynjolf to clear the bounty, so it’s not worth the hassle unless you’re intentionally roleplaying a chaotic character.
You also want to make sure you clear any active bounty in Riften before you start the initiation quest. If you have a bounty, the Thieves Guild members will refuse to talk to you, and you won’t be able to trigger the "Trinity Restored" quest even if you’ve completed all the required prerequisites. Just pay off the bounty at the Riften jail, or use the Thieves Guild’s own bounty clearing service if you don’t want to go to jail.
The last mistake to avoid is forgetting to loot all the chests in Nightingale Hall during the initiation. There are several hidden chests around the hall that have rare gems, gold, lockpicks, and even a few enchanted weapons, and most of them will disappear once you finish the initiation quest. Take 5 minutes to explore the hall before you do the final oath ritual, and you’ll walk away with a ton of extra loot for free.
Joining the Nightingales adds so much depth to any stealth playthrough, and the rewards are more than worth the time you’ll put in working through the Thieves Guild questline. Whether you’re a first-time Skyrim player or you’re doing a 100% completion run, taking the time to learn how to join the Nightingale in Skyrim will unlock some of the game’s most fun and unique content. Just follow the steps we outlined, avoid the common pitfalls, and you’ll be running around Riften in that iconic black and blue armor before you know it. If you’ve got a favorite Nightingale build or trick, drop it in the comments below—I’m always looking for new ways to shake up my next playthrough.
