Hardest Sekiro Shadows Die Twice Bosses, All 12 Ranked From Hard to Hardest

One of the major draws of Sekiro, and of FromSoftware games in general, are the exhilarating boss encounters. Exquisitely crafted, they will have you on the edge of your seat and pulling the hair out of your skull. As even common foes can reduce your health bar dramatically with a single blow, bosses really are no joke, and should not be treated lightly.

But not all bosses are created equal. For the sake of brevity, this list will focus on the main bosses of Sekiro, and not the dozens of mini-bosses scattered throughout Ashina. These are the named, unique big bads, that have their own move sets and mechanics. Some are optional, and others must be defeated to progress further in the game. SPOILERS AHEAD!

Without further ado, let’s take a look at the hardest Sekiro Shadows Die Twice bosses, ranked from tough to toughest.

Hardest Sekiro Shadows Die Twice Bosses, Ranked

12. Folding Screen Monkeys

Not so much a boss fight as it is a puzzle encounter, the Folding Screen Monkeys are still something you are going to have to deal with,  If you were able to figure this out on your own, then you deserve some kind of gold star. This is also mandatory, so buckle in.

There are four monkeys spread throughout the snowy shrine in which this “fight” takes place, and each needs to be dealt with in a particular way to proceed. The difficulty lies in the fact that the monkeys will warn each other if approached in the wrong way, and you will run around in circles while they mock you.

There is the purple “Seeing” monkey, the orange “Speaking” monkey, the green “Hearing” monkey, and the elusive “Doing” monkey… who is entirely invisible. They all exist to make your life a living hell.

Don’t let them have the last laugh, be sure to check out our Folding Screen Monkeys guide.

Hardest Sekiro Shadows Die Twice Bosses, Ranked

11. Emma, the Gentle Blade

Depending on certain choices you make during the course of your adventure, your erstwhile doctor can become an implacable foe during the latter half of the game. Trading her scalpel for a katana, Emma wields both with precision and compassion

Thankfully, on the spectrum of Sekiro boss encounters, the battle with the Gentle Blade is fairly straightforward. The engagement takes place in a fairly small arena, and she has access to several different techniques, but nothing near so complex as some of the other big bads. She has only a single health bar, meaning that this fight is not going to test your endurance like some others.

She does have something that the other bosses lack… Familiarity. Emma is with you from the very start of the game, and her aid is invaluable to your success. She is a constant companion and taking her life has a more emotional impact than nearly any other encounter in the game.

Hardest Sekiro Shadows Die Twice Bosses, Ranked

10. Gyoubu Masataka Oniwa

Gyoubu is the first true boss you are going to encounter in Sekiro, and he must be defeated in order to progress. He is tasked with guarding the gates of the Ashina Castle, and you engage him amongst the remnants of a great battle, surrounded by piles of broken weaponry and corpses.

Most of the difficulty of this encounter comes from the fact that it occurs so early on. At best, you may have increased your health and posture once, and this is only possible by defeating all mini-bosses before him, which is no easy feat. In fact, I found a lot of those mini-bosses to be tougher than Gyoubu!

He rides a magnificent steed and is armed with a massive polearm. He puts a lot of pressure on the player by constantly charging and never letting up. After a certain move, you will have the opportunity to grapple onto him, and if you have the Grappling Hook Attack skill, this can be a great way to inflict damage on him.

While he may look imposing, he is actually quite easy to parry. As long as you keep your cool, and strike out when possible, he will soon fall before you. And this is an exciting time because once you have access to the Ashina Castle proper, the game truly opens up…

If Gyoubu teaches you how to parry, then Lady Butterfly will teach you to dodge. While she is technically an optional boss, she is absolutely worth taking the time to overcome. The rewards received for defeating her are invaluable, and so is building the muscle memory required to do so.

Lady Butterfly is an incredibly agile shinobi that you encounter at the end of the Hirata Estates, and you confront her amidst the burning ruins of a Buddist temple. She fights with fistfuls of her signature butterfly kunai, which she will use to decimate you from both up close and from afar.

She has a variety of leaping attacks that will cause massive damage, but while in the air she is incredibly vulnerable. Make sure to have the Loaded Shuriken prosthetic tool equipped, and you can knock her out of the sky and score a free hit or two, which will help you on your path to victory.

She has a second phase, in which she summons illusionary ”children”, and her thrown kunai is followed by delayed flocks of deadly butterflies… And no-one ever suspects the butterflies. With a little patience and lot of trial and error, she too will be overcome.

If you are having trouble with her, be sure to check out our Lady Butterfly guide.

Hardest Sekiro Shadows Die Twice Bosses, Ranked

8. Guardian Ape

The Guardian Ape is an incredibly imposing foe that you will encounter somewhere around the middle section of the game. He is mandatory in order to progress further and is a roadblock that many players are likely to find themselves stuck on.

There are two phases to this battle, and they feel quite distinct from each other. In the first the Guardian Ape will, well, ape out on you, charging around on all fours and throwing poisonous poop at you, so make sure to bring along some antidotes. I’m not making this up.

After reducing his Posture and inflicting a Deathblow, the Guardian Ape will lose his head and gain a sword, making him a far deadlier opponent. His reach is incredible and will take quite some getting used to. Remember, as he is a beast-type, the Shinobi Firecracker is going to be your best friend in this fight.

If you are tired of all this monkey business, then be sure to check out our Guardian Ape guide.

Hardest Sekiro Shadows Die Twice Bosses, Ranked

7. Genichiro Ashina

Your encounter with Genichiro is set up from the very beginning of the game… He is the guy that cut your arm off, after all! Finally crossing blades with him is incredibly cathartic, and is very much a classic FromSoftware duel. It’s tough, fun, and my personal favorite encounter in the game.

The duel itself takes place on top of a tower, and there is quite a bit of room to maneuver. Wielding both katana and bow, Genichiro is devastating up close and just as threating from afar. Particularly cruel is his penchant for loosing an arrow at you as soon as you try and heal, although thankfully this is fairly easy to avoid.

The differences between ninja and samurai are really on display here, as his move sets are much more direct and militaristic. He also makes use of spacing in interesting ways, firing arrows as he approaches sword range, and leaping high into the air.

This fight has three phases and is of course required to proceed down the critical path. It seems to me that this is where the kiddy gloves really come off, as after Genichiro things really ramp up into the bizarre and wonderful bosses we expect from Miyazaki-san.If you are having issues with him, be sure to check out our Genichiro Ashina guide.

Hardest Sekiro Shadows Die Twice Bosses, Ranked

6. Great Shinobi Owl

Like father, like son. The battle with Great Shinobi Owl is an emotional one, and also extremely difficult. As Wolf was raised by Owl, and trained by him, there is a fantastic sense of climax to this fight… And you can be damn sure that the old dog, um, Owl, still has a few tricks up his sleeve.

This battle is optional, and without giving too much away, fighting your Shinobi father can even affect what ending you receive. This is cool though, as it means in order to experience every boss encounter you are going to need to replay the game, which is a great incentive to play through this masterpiece again.

As a master shinobi, his move set is not entirely conventional, employing shuriken and gas attacks that will debuff you. He is also no slouch with a blade and will punish you dearly for any mistakes made. As always, be patient and strike when you see an opportunity. The advantage of being an immortal ninja is that you can always try again.

If you get stuck, you can always check our Great Shinobi Owl guide to get you through.

Hardest Sekiro Shadows Die Twice Bosses, Ranked

5. Corrupted Monk

Perhaps the most unsettling boss in the game, at least in my opinion, the Corrupted Monk is a tough nut to crack. She will really put everything you have learned up to this point to the test, and in addition to punishing you physically, she has access to an assortment of illusionary techniques to make your life a misery.

The Corrupted Monk is quite interesting in that she can be fought twice, depending on the ending path you choose. She is encountered first as a mini-boss that is mandatory for story progression, with a single health bar. If you make certain choices during your journey, you will face her again in a true boss encounter, and she will be much more difficult.

Boasting three full health bars and Naruto-esque Shadow Clone Ninjutsu, this version of the Corrupted Monk is no joke, and one of the toughest boss encounters in the game.

Hardest Sekiro Shadows Die Twice Bosses, Ranked

4. Isshin Ashina

This climactic battle with Isshin Ashina, blade-master of the Ashina school of swordplay, is one of the greatest representations of a straight duel in the game. There are very few special techniques or attacks involved, just lighting-fast sword blows that will test your reflexes and push your Posture meter to the breaking point.

This fight takes place immediately after the encounter with the Gentle Blade, Emma, and as such is only possible while on the path to the Shura ending. If you choose to betray Kuro, then you must face the wrath of his steadfast guardians.

The really cool thing about this fight is that Isshin, as the progenitor of the Ashina sword school, has access to a lot of the same sword techniques as you do. Expect to see him using Ichimonji and other arts in addition to his plethora of Perilous Attacks, which include the full complement of thrusts, sweeps, and grabs.

Hardest Sekiro Shadows Die Twice Bosses, Ranked

3. Demon of Hatred

The Demon of Hatred is an extremely powerful optional boss, that should only be attempted once you have a very powerful Wolf with as many upgrades as possible. He hits like a truck and features three phases that increase in difficulty. If you have made it this far, then you likely know what you are in for.

The Demon is a true test of a players endurance. His Posture is so incredibly hard to break, that you are very likely to deplete his vitality bar first. This is very much opposed to how most other fights in Sekiro go and can seem counter-intuitive at first.

As is most often the case with FromSoftware’s more massive foes, the key to success is to actually get under the monster’s feet and inside his reach. From this perilous position, you will be able to evade his blows and dish out some damage of your own, although the true battle will actually be between you and the sometimes tricky camera.

Hardest Sekiro Shadows Die Twice Bosses, Ranked

2. Divine Dragon

The Divine Dragon is one of the most visually awe-inspiring bosses From has come up with to date, and is no slouch either. Reminiscent of Bloodborne’s battle against Rom, The Vaccuous Spider, the Divine Dragon features multiple phases, the first of which is against many smaller opponents.

After having assumed his true form, The Divine Dragon boss fight will involve some platforming elements that will require precise timing, with a swift death awaiting any minor mistake. And while this encounter is truly tough, it’s hard not to be struck by how freaking cool it is as well. I mean, you are literally trading blows with a god.

Once completed though, you can’t help but feel bad for the guy. It echoes the original Dark Soul’s iconic Sif fight, and although by this point in your quest you have vanquished countless enemies, there is a certain sense melancholy in disposing of this beautiful creature.

Hardest Sekiro Shadows Die Twice Bosses, Ranked

1. Isshin, The Sword Saint

The final boss you will encounter in Sekiro is Isshin, The Sword Saint. Fighting him will be grueling, frustrating, and even cruel at times… But as is so often the case with these games, the feeling of accomplishment after he finally falls will make it all worthwhile, and you will mostly forget about the misery he brought you. Mostly.

While it is still early days yet, many fans of the Soulsborne series have declared Isshin to be the most difficult encounter in the entire series, along with such other nightmarish encounters as Sister Freide and the Orphan of Kos. Certainly, there will be players that never beat him, ending their journey in sight of the finish line. I like to think Miyazaki-san smiles to himself, every time someone rage quits.

There are four phases to the fight, each more deadly than the last. He even swaps weapons between phases, taking up a spear and forcing you to change tactics. The Sword Saint is the hardest boss encounter in Sekiro, and the last thing standing between you and New Game Plus, where you can look forward to fighting each of the above bosses again… Only this time, they are even tougher.