If you’ve spent any amount of time wandering Skyrim’s cold, war-torn roads, you’ve probably heard hushed whispers about the Nightingales: shadowy, immortal agents of the Daedric Prince Nocturnal, who guard the secrets of thieves and rule over the dark corners of Riften’s underbelly. I wrote this guide after my third playthrough, when I finally took the time to work through the full Thieves Guild questline and realized just how easy it is to miss key steps if you’re rushing through quests. Whether you’re playing a sneaky Khajiit pickpocket, a sneaky Nord warrior who wants to avoid dragon fights half the time, or anything in between, knowing how to become a Nightingale in Skyrim opens up some of the game’s most fun, unique content you won’t find anywhere else.
Prerequisites to Start Your Journey to Become a Nightingale in Skyrim
First off, let’s bust a common myth: You don’t need to have 100 Sneak or Lockpicking to start this questline. I started my first Nightingale run with a level 12 Breton mage who had 15 Sneak and still got through every quest without too much trouble. The only real prerequisite is that you have to start the core Thieves Guild questline in Riften. To do that, head to the Riften market when it’s open between 8am and 8pm, and look for a red-haired Nord named Brynjolf. He’ll approach you with a small job to frame a local merchant, and that’s the first step to joining the guild. So you have an active bounty in Riften, you’ll want to pay that off first. Guards will stop you before you can talk to Brynjolf if you’re marked as a criminal, and if you resist arrest, you’ll make the entire questline unavailable until you resolve your bounty. You also don’t need to complete any side quests for the Thieves Guild before you start the main Nightingale arc, but doing a few will help you level up your sneak and lockpicking skills a little to make later quests easier. You can even use magic or heavy combat to get through most of the dungeon sections if stealth isn’t your playstyle, no one will penalize you for it.
Key Quests You Need to Complete to Earn Nightingale Status
Once you’re a full member of the Thieves Guild, you’ll work your way through a string of main quests that lead you straight to the Nightingale initiation. The first big turning point is the “Speaking with Silence” quest, where you’ll team up with Karliah, a former Thieves Guild member who’s been framed for murdering the previous guild leader. You’ll learn the truth about the Nightingales during this quest, and find out that the guild’s falling apart because it lost Nocturnal’s blessing years earlier. A lot of players worry that joining the Nightingales will block them from other questlines, but You will not be locked out of other questlines by joining the Nightingales. I’ve completed the Companion, Dark Brotherhood, and College of Winterhold questlines on the same character that’s a Nightingale, no issues at all. The only quest you have to finish to officially become a Nightingale is “Trinity Restored”, where you, Brynjolf, and Karliah will travel to the Twilight Sepulcher, Nocturnal’s hidden temple, to take the Nightingale oath. You’ll have to fight a few small groups of undead and bandits along the way, but nothing too challenging even for lower-level characters. Once you take the oath, you’re officially a Nightingale, and you’ll get access to all the associated perks right away.
Exclusive Perks You Unlock as a Nightingale
Joining the Nightingales isn’t just for roleplay fun. You get a ton of exclusive, high-value gear and perks that make the questline worth doing even if you don’t usually play stealth builds. Some of the best rewards include:
- Nightingale Armor set: Light armor with built-in Sneak boosts, frost resistance, and unlimited stamina for one hour once per day, plus it looks way sleeker than the scuffed standard Thieves Guild armor. If you upgrade it at a workbench with the right perks, it’s competitive with the best light armor sets in the game.
- Nocturnal's Blessing: A rotating daily perk that changes every 24 in-game hours. The three options are 25% better lockpicking success, 25% higher pickpocket chance, or 25% extra sneak attack damage, all of which are useful for any build that ever wants to sneak past guards or loot a house without getting caught.
- Access to the Twilight Sepulcher: A hidden dungeon with rare loot, including unique poisons, filled black soul gems, and gold piles that respawn every 30 in-game days. It’s a great spot to restock on supplies if you’re running low on gold or enchantment materials.
- Nightingale Blade and Bow: Unique level-scaling weapons with frost damage and built-in soul trap enchantments. If you wait to get them at a higher level, they hit harder than most unique weapons you’ll find in random dungeons.
Common Mistakes to Avoid When Joining the Nightingales
After running this questline on four different playthroughs, I’ve picked up on a few common mistakes that can ruin your Nightingale run if you’re not paying attention. First, Wait until you're at least level 30 to complete the final Nightingale quest if you want the highest stat versions of all unique gear. The armor and weapons scale to your level when you receive them, so if you finish the quest at level 10, you’ll get a low-stat version that you can’t upgrade later. It’s fine to start the questline early, just hold off on finishing “Trinity Restored” until you hit level 30 if you care about max stats. Second, never sell or discard your Nightingale gear, as there is no way to replace it if you lose it. I made this mistake on my first playthrough when I sold the Nightingale bow to a blacksmith for 500 gold, and I spent hours looking for a way to get it back before I realized it was gone forever. If you don’t want to use it, store it in a safe chest in a house you own, never in a random container that respawns. Third, don’t attack Karliah or Brynjolf at any point during the questline. If you hit them by accident with a shout or a stray arrow, reload your save right away. If they become hostile, you’ll fail the entire questline permanently, and you’ll never get to become a Nightingale on that playthrough. Finally, don’t forget to return to the Twilight Sepulcher if you want to swap your Nocturnal’s Blessing perk early. You don’t have to wait 24 hours for it to rotate; just head back to the altar in the Sepulcher and interact with it to pick whichever perk you want for the day.
Becoming a Nightingale in Skyrim is one of the most satisfying faction experiences in the entire game, with a great story, memorable characters, and rewards that are useful for almost any playstyle. You don’t have to be a dedicated stealth player to enjoy the questline, and the perks you unlock will make exploring, looting, and even fighting dragons a lot easier. Next time you’re wandering through Riften, stop and talk to Brynjolf, you won’t regret the time you put into joining the Nightingales. I still keep my Nightingale armor in my inventory on every playthrough, even when I’m running a two-handed warrior build, just for those moments when I want to sneak past a bandit camp instead of fighting every single enemy.
