Skyrim: The Hardest Quests To Complete, Ranked

Summary

• Skyrim quests offer diverse challenges, from difficult decisions like saving or killing a beloved character to facing powerful enemies.
• Main quests like The Way of the Voice and Elder Knowledge pose challenges due to perilous paths, powerful enemies, and long journeys.
• Completing tough quests like Paarthurnax and Lost to the Ages requires strategic planning, combat skills, and defeating strong foes.

There are lots of quests to encounter throughout Skyrim and its expansion packs. While some missions are relevant to certain factions and storylines, others are standalone side quests. Many of the missions you can play in Skyrim contain unique challenges that range from collecting alchemy ingredients to defeating a legendary warrior.

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If you're looking for a challenge, then the following quests are the perfect adventures to partake in. With that in mind, here are the hardest challenges waiting for you in the land of Skyrim.

Updated April 29, 2025 by Britt Poteet: With the expansive number of quests available in Skryim, we added a few more difficult ones for veteran players in case you've already solved the others on the list. While these quests are difficult, they add immersive value to the game.

17 The Cure For Mastatic.aayyy.com/topic/dn/ess

Cicero is a notable character in the Dark Brotherhood questline. Although he betrays the guild at the beginning of this mission, he's still a beloved character among the Elder Scrolls fanbase, which makes whether or not you side against him a difficult decision. You'll have the chance to kill Cicero at the end of the quest, but you can also set him free, and then he'll become a follower after completion of the Dark Brotherhood questline.

In addition to this difficult decision, The Cure For Mastatic.aayyy.com/topic/dn/ess is also challenging in that you have to explore an old Dark Brotherhood sanctuary and defeat many ghostly enemies on your way to finding Cicero. Overall, this quest is one of the hardest quests in Skyrim's Dark Brotherhood questline.

16 The Way Of The Voice

The Way of the Voice is one of the most iconic quests in Skyrim not just because it's a main quest, but also because it requires you to climb a perilous path full of dangers — such as dangerous animals that are difficult to defeat when you're a low level. You'll usually start this quest at a lower level since it's one of the first main quests in Skyrim, so it's quite a challenge at first.

You'll also need to climb hundreds of steps to get to the top and meet the Greybeards, making it not only difficult but a long quest overall. To top it all off, the beginning of this upward path is in Ivarstead, which you can't get to via a regular carriage — meaning you'll need to walk there. Overall, this quest is difficult both because of the long walk and the powerful enemies you encounter on the steps.

15 Paarthurnax

Paarthurnax is one of the most interesting characters in Skyrim. He has both an interesting backstory and he's very kind to the Dragonborn, putting his past aside to help save the world from Alduin. However, Delphine and The Blades will eventually approach the Dragonborn asking for them to kill Paarthurnax, which is optional.

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Killing Paarthurnax is a challenge since he's a powerful dragon, but it's also hard because he's changed a lot — and the Blades may be wrong in condemning him after he helped the Dragonborn and their allies. The choice is up to you, but both the decision and potential battle are very difficult.

14 Destruction Ritual Spell

The content in the Destruction Ritual Spell quest is difficult, but what makes it particularly challenging is that you have to reach level 90 in the Destruction skill to start it. Upon talking to Faralda at the College of Winterhold, you can complete this quest to earn access to a powerful selection of Destruction skills.

You also have to travel to three different locations before the quest is complete, which means you'll have to do a lot of walking and fighting powerful enemies throughout your journey if you want to unlock the higher tier Destruction spells. The trip through multiple locations, combined with the grind required to reach Destruction level 100, makes this one of the toughest missions in Skyrim.

13 Blood On The Ice

Crime fans will enjoy solving murders in the Blood on the Ice quest in Windhelm, though you may be surprised at how difficult it is. After several young women are brutally mutilated, you are recruited to find The Butcher responsible.

This extensive and detailed quest involves interrogating witnesses, detailed autopsies, and a necromantic sacrifice as you search for the serial killer. There’s potential to completely miss rewards and fail the investigation, so tread carefully. Once you figure it out, there are various rewards depending on the choices you make.

12 Hitting The Books

The College of Winterhold questline has quite a few lengthy quests that take a lot of power and time to complete. One of the longest and most difficult missions you can complete for this faction is Hitting The Books, which is one of the first main quests you get sent on by the college.

After speaking to Urag, he'll request that you collect lost books from Fellglow Keep. There are magical enemies guarding these books, so getting them is quite the challenge. In addition to the long dungeon with tons of enemies, you'll also have to fight a mage named The Caller, which is a tough boss fight that will test your strength against magical attacks.

11 At The Summit Of Apocrypha

At The Summit Of Apocrypha is the final quest in the Dragonborn DLC's main storyline. During this quest, you have to travel through the Black Book: Waking Dreams and defeat Miraak. Since Miraak is essentially the final main boss in Skyrim, he's quite difficult to defeat.

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Not only will you have to face Miraak, but there are also dragons present during the fight, adding double the trouble to this mission. Miraak is particularly powerful since he can use shouts and has a unique equipment set that grants him many powerful bonuses.

10 The Break Of Dawn

Daedric Artifact quests are always on the difficult side, and The Break of Dawn is no exception. After encountering Meridia’s Beacon, you speak with the Daedric Prince herself. While journeying to cleanse her temple of evil, you have to fight a Necromancer and his corrupt shades, who throw heavy spells your way.

If this encounter is accessed at Level 12, the fight is quite a challenge, requiring a lot of strategic planning and strong combat skills. However, the reward of the Dawnbreaker weapon is well worth it in the end.

9 The Wolf Queen Awakened

The Wolf Queen Awakened is a mission that you must complete to gain the respect of Solitude and Elisif The Fair. Although the quest has many trivial steps, the hardest part is by far the final fight. Before you face Potema, you'll need to defeat waves of Draugr. Unfortunately, this section of the fight is much too difficult for low-level adventurers, especially if you're playing on a high difficulty.

If that wasn't hard enough, you also face Potema herself as the final boss, which is difficult since she can use Destruction magic and summon Atronachs, so fighting many magical enemies is a core component of this battle. Once you defeat Potema, you'll feel an immediate sense of pride that you sent The Wolf Queen to her grave.

8 The Black Star

The Black Star is Azura's Daedric Quest in Skyrim. Daedric Quests are known for being more difficult than standard side missions, but The Black Star takes this to an entirely different level because of the nature of the enemies you face.

After beginning the quest by traveling to the Shrine Of Azura, you need to recover Azura's Star, which is the easy part. Next, you have to enter the star and defeat Malyn Varen, which is easier said than done. Dremora minions are also a threat inside the star, which are difficult in their own right, especially on higher difficulty settings.