Cuphead Bosses Ranked by Difficulty, Including Delicious Last Course Bosses

Cuphead Bosses Ranked by Difficulty, Including Delicious Last Course Bosses
Image Credit: BossLevelGamer/MDHR

Cuphead bosses are notoriously difficult but they’re also some of the most imaginative, mechanically impressive, and visually striking bosses in all of gaming. Studio MDHR did a bang-up job designing these enemies and they recently graced us with a whole slew of new challenging fights via The Delicious Last Course DLC. Now that we’ve had over a week to sink our teeth into the DLC, we figured it was high time we did a complete ranked list of all Cuphead bosses. And I do mean complete.

This list will feature all the main bosses from the base game, all the mini bosses, and all the Delicious Last Course Bosses, complete with the secret boss fight. In total, we’re looking at no less than 40 bosses, which will make this list even more extensive than our Elden Ring bosses ranked list. But still a bit shorter than our Hollow Knight bosses ranked list. As you can probably tell by now, we love ranking bosses.

Before we get started, just keep in mind that this is largely a subjective ranking since everybody experiences the game a bit differently. The bosses we found to be the hardest might very well be the ones you beat in a couple of tries, and vice-versa.

With all of that out of the way, join us as we take a look at every Cuphead boss ranked by difficulty.

40. Mangosteen (Mini Boss)

cuphead characters bosses
Image Credit: Studio MDHR Entertainment Inc.

Mangosteen is one of the nine mini bosses you’ll have to defeat before facing off against King Dice. All of them are pretty easy to deal with compared to the main Cuphead bosses, but Mangosteen is arguably the weakest of the bunch. The mini boss’ sole attack is a breeze to dodge and his accompanying billiard chalks don’t pose much of a threat either. This fight shouldn’t take more than 20-30 seconds if you know what you’re doing.

39. Pirouletta (Mini Boss)

cuphead boss ranked
Image Credit: Studio MDHR Entertainment Inc.

Pirouletta is another one of King Dice’s henchmen. Just like the aforementioned 8-ball, this mini boss only has a single attack, however, she also dances around the room from side to side and will trample you to death if you’re not careful. The standard way of avoiding her when she dances is by Parry Slapping the poker chips, but you’ll have a much easier time simply using the Smoke Dash charm instead. With the charm equipped, you’ll be able to make short work of Pirouletta in no time.

38. Chips Bettigan (Mini Boss)

cuphead king dice bosses
Image Credit: Studio MDHR Entertainment Inc.

Next up we have Chips Bettigan and you’re probably starting to see a pattern by now. Most of the mini bosses are pushovers, so there’s no way we could have ranked them anywhere else but at the bottom. To be fair, a few of the mini bosses can be fairly challenging but that’s not the case with Chips Bettigan. The only reason why Chips is higher on the list than the previous two is because his attack, while easy to dodge, can be a bit unpredictable.

37. Hocus Pocus (Mini Boss)

cuphead bosses easiest to hardest
Image Credit: Studio MDHR Entertainment Inc.

We’ve all seen magicians pulling rabbits out of hats, but what would happen if said rabbits were magicians themselves? Well, you would probably get something like Hocus Pocus. This magical bunny has a couple of tricks up his sleeves, including an attack where he summons a circle of rabbit skulls that surround the player. This attack is pretty hard to dodge if you’re not using the Smoke Dash charm, which is why we’re placing Hocus Pocus higher than some of the other mini bosses.

36. The Pawns (Dlc Mini Boss)

how many bosses are in cuphead
Image Credit: Studio MDHR Entertainment Inc.

Finally, we can start talking about some Cuphead DLC bosses. You’ll run into a bunch of chess-themed mini bosses during The Delicious Last Course, including these guys. Fittingly enough, The Pawns are the weakest challengers and can be dispatched with relative ease, provided you’re good at Parry Slapping. You can’t shoot The Pawns so the whole fight revolves around slapping and jumping. While a bit annoying at times, the fight is ultimately easy by Cuphead standards.

35. Mr. Wheezy (Mini Boss)

how many bosses in cuphead
Image Credit: Studio MDHR Entertainment Inc.

Smoking can kill you in real life, but in Cuphead you can kill smoking. Or at least the personification of it known as Mr. Wheezy. This cigar mini boss isn’t very tough but he moves around quite a bit and his looping fireballs can be pretty annoying. In addition, you also have to dodge cigarette bats whenever Mr. Wheezey teleports between ashtrays. There’s more going on in this fight compared to the other ones we’ve covered so far, but ultimately Mr. Wheezy should pose very little challenge to an experienced Cuphead player.

34. Phear Lap (Mini Boss)

cuphead boss list
Image Credit: Studio MDHR Entertainment Inc.

Phear Lap would definitely be much higher if we were ranking Cuphead bosses based on their design. Not only are you beating a dead horse but you’re doing it at a horse racing track and you’re getting gifts straight from the horse’s mouth. People say you shouldn’t look a gift horse in the mouth but you should definitely try to avoid the gifts coming out of this horse’s mouth. I’m sure there are some other puns and sayings hidden around here, but you get the idea. This may not be one of the hardest boss fights but it’s definitely one of the most cleverly designed ones.

33. Tipsy Troop (Mini Boss)

all cuphead bosses
Image Credit: Studio MDHR Entertainment Inc.

You really have to love the design of some of these bosses. The Tipsy Troop is a trio of alcoholic drinks that work together when trying to take down the player. Each of the three drinks has a different attack, and while individually the attacks are nothing to write home about, they are a nuisance when combined together. Fortunately, once you take one of these drunken rascals down, you also stop one of the trio’s attacks. This is one of those rare instances when a boss fight becomes progressively easier. All you need to worry about is the first part of the fight when all three of them are attacking.

32. Pip and Dot (Mini Boss)

cuphead casino bosses
Image Credit: Studio MDHR Entertainment Inc.

Next up we have another casino mini boss, or should I say, bosses? Pip and Dot are a dynamic domino duo you’ll have to fight while on the move. The stage itself is the biggest hassle here as you’ll need to constantly jump over spikes while dodging attacks. Pip and Dot’s attacks are slow and well telegraphed but they can still hit you if you’re not paying attention. Ultimately, though, the stage is the main reason why this boss fight is so high up on the list. Pip and Dot themselves are pretty easy to deal with. 

31. The Queen (Dlc Mini Boss)

cuphead dlc bosses
Image Credit: Studio MDHR Entertainment Inc.

The Queen is one of the most intimidating DLC mini bosses due to the sheer number of things flying all over the screen during the course of the fight. Her main attack can be difficult to dodge but it doesn’t take more than a couple of tries to get used to the pattern. Her secondary attack is much easier to deal with by comparison. You’ll need to once again make good use of those Parry Slaps not just to negate the secondary attack, but also to fire the cannons since you can’t shoot at her directly.

30. The Rook (Dlc Mini Boss)

cuphead bosses ranked
Image Credit: Studio MDHR Entertainment Inc.

The Rook is one of the least interesting Cuphead bosses in my opinion. I really like the design of the boss but the fight itself isn’t very memorable. Instead of fighting the boss directly, you’ll spend the entire fight parrying pink heads spawning out of The Rook’s grindstone. You’ll need to hit each head a couple of times to send it flying towards the boss and damage him. You can easily mess up and get damaged by the heads yourself but the challenge level of this fight is ultimately still quite low.

29. Mr. Chimes (Mini Boss)

all bosses in cuphead
Image Credit: Studio MDHR Entertainment Inc.

Mr. Chimes is another one of the Cuphead bosses you’ll encounter in the casino before fighting King Dice. And this one may end up giving you a run for your money. This fight is pretty unique as it involves a memory game where you have to match various pairs of cards. You won’t be able to start fighting Mr. Chimes until you find at least one pair, but be careful because this monkey fights back and he has a lot of health points. The Mr. Chimes battle can drag on for quite a while, especially if you’re bad at memory games, which is why we’re placing the cymbal monkey higher than all the other casino mini bosses.

28. Goopy Le Grande (Isle One Boss)

cuphead bosses in order
Image Credit: Studio MDHR Entertainment Inc.

Goopy Le Grande is by far one of the easiest Cuphead bosses, which shouldn’t be too surprising considering he’s also one of the first bosses you’ll encounter in the game. You’ll spend most of the first phase dodging Goopy’s bouncing attack while occasionally evading his punches. Phase two is pretty much identical except for the fact that Goopy is larger and has more range. Meanwhile, the third phase requires patience more than anything else. Goopy Le Grande is a great boss to introduce players to the game but the fight isn’t particularly hard. Same with the next one.

27. The Root Pack (Isle One Boss)

cuphead all bosses
Image Credit: Studio MDHR Entertainment Inc.

If you don’t want Goopy Le Grande to be your very first Cuphead boss fight, your only other option is The Root Pack. This one is a bit harder, but not by much. Probably the most interesting aspect of this fight is the ability to skip the second phase and unlock a secret phase instead. Skipping phase two speeds things up a bit but it also makes phase three considerably harder. Now instead of fighting just Chauncey Chantenay you also have to simultaneously deal with a new vegetable-themed enemy called Horace Radiche.

26. King Dice (Hell Boss)

cuphead dice boss
Image Credit: Studio MDHR Entertainment Inc.

King Dice is one of the toughest Cuphead bosses if you include all his minions to be part of the fight, which is technically how it works. They’re not very difficult to deal with individually, but together they combine to provide the player with one hell of a challenge. But since we are ranking them individually here, King Dice by himself isn’t particularly strong. The fight does require good timing and precision but only features one phase. Once you figure out how to slap the cards without taking damage, the fight becomes a breeze.

25. The Knight (Dlc Mini Boss)

cuphead bosses names
Image Credit: Studio MDHR Entertainment Inc.

Knights used horses to charge into battle but in the world of Cuphead it looks like knights are horses. Or at least this one is. Going up against The Knight feels just like playing a fighting game. This is a 1v1 duel taking place inside a small arena and you don’t have to worry about weird stuff flying all over the screen. The Knight is a melee combatant that fights with a sword and shield and alternates between several attacks. In typical video game fashion, The Knight has a single weak spot you’ll need to repeatedly slap in order to damage him. Not the toughest fight but definitely one of the most interesting DLC bosses.

24. Ribby and Croaks (Isle One Boss)

cuphead boss
Image Credit: Studio MDHR Entertainment Inc.

Cuphead bosses often come in pairs. This particular pair is comprised of boxing frogs with lots of tricks up their sleeves. Or rather, gloves. The first phase is just a bit of a warm-up, with the real fighting kicking off in phase two when Ribby and Croaks surround the player while attacking simultaneously. The third phase is not to be sneezed at either but you shouldn’t have too much trouble clearing it provided you don’t get distracted by how weird it is. Ribby and Croaks are fairly tough for a couple of Isle One bosses but there are way tougher opponents still to come.

23. The Bishop (Dlc Mini Boss)

boss cuphead
Image Credit: Studio MDHR Entertainment Inc.

And next up on our list of Cuphead bosses ranked by difficulty we have The Bishop. I’m sure some people will disagree but I feel like this is the hardest mini boss in the game. The fight requires you to jump around a lot while dodging bells as you attempt to put out candles. Once all the candles have been extinguished, you can slap The Bishop (or rather, his head) around but you’ll only be able to get a single hit in before the head recoils and starts lighting up candles again. Rinse and repeat. Although I really love the design of this boss, the fight itself can be a huge hassle.

22. Cagney Carnation (Isle One Boss)

cuphead flower boss
Image Credit: Studio MDHR Entertainment Inc.

Easily one of the most iconic Cuphead bosses thanks to its design, Cagney Carnation can be encountered towards the end of Isle One. This flower boss only has two phases but they’re both pretty difficult to deal with. In phase one, you’ll need to do a lot of jumping between platforms while dodging falling projectiles, boomerangs, and more. Luckily, phase two is easier even if Cagney’s attacks get faster, so if you can get past that first phase you should be golden. 

21. Angel and Devil (Secret Boss)

cuphead secret boss
Image Credit: Studio MDHR Entertainment Inc.

While the base game does have a few secret phases, there are no secret bosses. Thankfully, we just recently got a secret boss fight via The Delicious Last Course. This fight looks intimidating at first because it seems like you’re going up against two opponents at once, however, you actually only have to worry about the Devil since Angel’s attacks don’t hurt the player. The Devil will always face the player so it’s best to avoid turning unless absolutely necessary. The secret boss fight is moderately difficult but doesn’t have multiple phases so it shouldn’t take too long to beat once you figure out the attack patterns.

20. Glumstone the Giant (Dlc Boss)

cuphead boss fight
Image Credit: Studio MDHR Entertainment Inc.

Glumstone the Giant is one of the first bosses you’ll encounter in The Delicious Last Course DLC. This boss makes a great first impression as he summons flocks of geese with his whistle nose and reveals the potion-brewing gnomes living in his mouth. It’s all very weird and wonderful. There’s a lot going on in phase one but things dial down a bit in the other two phases. An enjoyable fight overall but only moderately difficult.

19. Baroness von Bon Bon (Isle Two Boss)

cuphead candy boss
Image Credit: Studio MDHR Entertainment Inc.

Next up we have the sweetest Cuphead boss ever, Baroness von Bon Bon. This is one of those fights that can vary in terms of difficulty so it’s a bit hard to rank, but number 19 seems appropriate. The Baroness has five loyal subjects and she will force you to fight three of them before engaging you herself. Some of these opponents are harder to dispatch than others and the game assigns the challengers at random. This fight will be harder for some people than others depending on each player’s luck. On the bright side, at least you can expect the last phase to be the same every time.

18. Captain Brineybeard (Isle Three Boss)

cuphead hardest bosses
Image Credit: Studio MDHR Entertainment Inc.

A lot of people find Captain Brineybeard to be one of the most annoying of all Cuphead bosses and it’s easy to see why. The fight looks deceptively simple at first until you realize that you’re fighting not just the captain but his ship as well. Oh, and there are also various sea creatures to deal with and an annoying barrel that hangs over you throughout the entire fight. But the most frustrating thing here is the fact that phase one seems to last forever even though it’s actually split into three different phases. There are no crazy transformations like in other boss fights, though. That only happens in phase four.

17. Moonshine Mob (Dlc Boss)

cuphead bosses list
Image Credit: Studio MDHR Entertainment Inc.

I’m a bit surprised it took MDHR this long to make a boss fight revolving around bootlegging and criminal gangs considering the game is inspired by the 1930s when Prohibition in the United States was still a thing. In any case, I’m glad they eventually did it. And I’m even happier that it turned out so well. The Moonshine Mob fight is awesome and one of the funniest in The Delicious Last Course. Nay, the entire game. The fake “Knockout” in phase three is absolutely brilliant and probably got more than a few gullible players killed. I may or may not be one of them.

16. Sally Stageplay (Isle Three Boss)

cuphead boss tier list
Image Credit: Studio MDHR Entertainment Inc.

Isle Three is where things really start to ramp up. Every boss here will test your skills to a greater or less extent, including Sally Stageplay. She’s one of the weakest bosses on the island in my opinion but she’s definitely not to be underestimated. This is a four-phase fight with some optional secret phases that can be triggered by dropping a chandelier on Sally’s husband. Interestingly enough, the first half of the fight is arguably much harder than the second half regardless of whether you activate the secret phases or not. Do your best to survive the first half and you shouldn’t have much trouble clearing the second one.  

15. Werner Werman (Isle Three Boss)

cuphead bosses
Image Credit: Studio MDHR Entertainment Inc.

The Werner Werman boss fight is basically just a twisted version of Tom & Jerry. “Jerries” was a slang term used by the British during WW1 to refer to the Germans (who, in turn, called the British “Toms”), hence why the Cuphead version of the lovable mouse has a German name. Fun facts aside, the reason why we’re placing Werner Werman so high up on the list is mainly because of the stage. You need to fight Werner in a very confined arena where there’s little room for error. Things get claustrophobic at certain points during the fight, especially during phase two. You’ll need both skill and precision to win this one.

14. Mortimer Freeze (Dlc Boss)

hardest cuphead bosses
Image Credit: Studio MDHR Entertainment Inc.

It’s time to look at some new Cuphead bosses again, starting with Mortimer Freeze. This fight is pretty intense from start to finish and involves a lot of moving around. The first phase isn’t too bad if you can manage to dodge the icicles as Mortimer’s other two attacks are slow and well telegraphed. Phase two gets a bit harder but it’s the third phase you’ll want to watch out for. Here, you’ll have to fight on constantly moving platforms while evading four different types of attacks. If that wasn’t already bad enough, the boss zips from one side of the arena to the other when you least expect it.

13. Hilda Berg (Isle One Boss)

cuphead moon boss
Image Credit: Studio MDHR Entertainment Inc.

Hilda Berg is the first Cuphead boss that elevated my heart rate to dangerous levels when I first played the game. The bosses on Isle One are relatively easy to beat, as one might expect from the opening section of the game. That’s not really the case with Hilda Berg, though. Not only is this the first aerial boss battle in the game but it also has tons of phases. Similar to the Baroness von Bon Bon fight, some of the phases are randomized so you’ll never know exactly what to expect. But the hardest part is definitely the last phase due to those incredibly annoying UFOs. I hate those things.

12. The Howling Aces (Dlc Boss)

best cuphead boss
Image Credit: Studio MDHR Entertainment Inc.

Cuphead gives aerial dogfighting a whole new meaning with The Howling Aces, a boss fight where you get to fight actual dogs. The first two phases are filled with all sorts of silly nonsense like a bulldog pilot using a cat as a cannon and jetpack-wearing puppies barking letters at you. It’s all great fun. However, the biggest highlight is definitely phase three where the Chinook dog flips the entire screen, testing your spatial awareness in the process. Easily one of the best moments of the DLC, and the rest of the fight isn’t too shabby either.

11. Djimmi the Great (Isle Two Boss)

cuphead bosses ranked by difficulty
Image Credit: Studio MDHR Entertainment Inc.

Is it just me or are all the aerial boss fights in this game really hard? The fight against Djimmi the Great isn’t even that difficult compared to some of the others but it’s still enough to frustrate you to no end. The first phase really sets the tone for what to expect when Djimmi pulls out a treasure chest filled with one of three things. If you get the jewels, just restart, it’s not worth the pain. There are no less than four additional phases after that, each more annoying that the last. Phase four can be skipped but doing so will make the last phase harder. Either way, you’ll have your work cut out for you with this one.

10. Rumor Honeybottoms (Isle Three Boss)

cuphead bee boss guide
Image Credit: Studio MDHR Entertainment Inc.

It’s pretty clear that this fight was designed to raise our anxiety levels through the roof. And you know what? It does exactly what it was designed for, so good job MDHR. Seriously, though, the fact that you have to jump from platform to platform throughout the entire fight makes this one of the few instances where the stage itself is more infuriating than the actual fighting. Don’t get me wrong, Rumor Honeybottoms is a difficult boss, especially during the third phase, but it’s the platforming that always gets my goat.

9. Beppi the Clown (Isle Two Boss)

hardest bosses in cuphead
Image Credit: Studio MDHR Entertainment Inc.

Now here’s a real high-class bout! This is one of those fights that looks like a lot of fun when you’re watching someone else play it. Try to play it yourself, however, and you’ll quickly find out that Beppi the Clown isn’t all fun and games. Admittedly, the first phase is pretty easy but the fight gets progressively harder with each subsequent phase. And there are four of them in total. By the end of it, you’ll probably start hating clowns, balloon animals, merry-go-rounds, and just amusement parks in general. Oh, and don’t even get me started on those darn penguins.   

8. Cala Maria (Isle Three Boss)

cuphead mermaid boss
Image Credit: Studio MDHR Entertainment Inc.

This has to be one of the most beautifully animated and charming boss fights in the game. Don’t get too distracted by the siren, though, because Cala Maria also happens to be one of the most difficult Cuphead bosses. The fight only has three phases but each of them drags on forever thanks to Cala’s significant health pool. It’s a good idea to get more health yourself for this fight because there’s a lot of stuff here that can hurt you. Cala can stun the player in both phase two and phase three so chances are you’ll probably get hit at least a couple of times before the end of the fight.

7. Wally Warbles (Isle Two Boss)

cuphead bird boss
Image Credit: Studio MDHR Entertainment Inc.

Wally Warbles is a cuckoo bird encased in a cuckoo clock. Oh, and he’s also more than a bit cuckoo judging by his fighting style. Phase one seems pretty manageable at first since all you have to do is dodge some eggs and the occasional finger bullets. But once Wally starts flapping around furiously and sending feathers in all directions you know you’re in trouble. Dodging the feathers without taking any damage requires a ton of precision, especially when he performs the attack twice in a row. The last two phases are comparatively easier but they’re definitely not a walk in the park by any means.

6. Esther Winchester (Dlc Boss)

cuphead boss names
Image Credit: Studio MDHR Entertainment Inc.

Holy cow! Esther Winchester has to be one of the most imaginative – and disturbing – Cuphead bosses. The fight starts off with the player going up against a literal cow girl but things get even more bizarre in phase three when she turns into sausages and begins chucking steaks at you. Esther is so relentless that she keeps fighting even after transforming into a can of meat in phase four. You have to appreciate that fighting spirit. As far as the difficulty is concerned, the fight against Esther Winchester definitely deserves to be in the top 10.

5. Phantom Express (Isle Three Boss)

cuphead hardest boss
Image Credit: Studio MDHR Entertainment Inc.

Hats off yet again to MDHR for designing these incredible boss fights. The level of creativity is off the charts in this battle where you have to fight the inhabitants of a ghost train. And eventually the train itself. The fact that you’re stuck on a relatively small platform for the entirety of this fight makes this level extremely punishing. Not just that but you’ll have to operate the platform yourself. The entire encounter is pretty brutal but the final phase has to be the most memorable one, not just because of its difficulty but because you’re fighting a train that gallops like a horse. Props to whoever came up with that idea.

4. The Devil (Hell Boss)

cuphead final boss
Image Credit: Studio MDHR Entertainment Inc.

And next up we have Cuphead’s final boss, The Devil himself. This guy is so confident in his powers that he spends most of the first phase sitting on his throne. I guess you can lean back and relax when you have incredible magic powers, like the ability to turn your head into a giant spider. I suggest saving up your Super for phase three because that’s the hardest one of the bunch. The final phase could prove even more difficult for some players since you’ll only have one platform remaining and nowhere to run. However, The Devil only has a few hit points left by phase four and goes down quickly.

3. Grim Matchstick (Isle Two Boss)

hardest boss in cuphead
Image Credit: Studio MDHR Entertainment Inc.

To call Grim Matchstick one of the most difficult Cuphead bosses would be an understatement. Fights that incorporate a lot of platforming are always challenging and this one is no exception. The fact that you’re fighting in the clouds and everything is constantly moving makes things even worse. This fight would have been difficult even if you were fighting a weak boss, let alone a strong one like Grim. Granted, his attacks are not the craziest ones you’ll encounter in the game but they’re enough to turn the fight into a nightmare when combined with the punishing nature of the level.

2. Chef Saltbaker (Dlc Boss)

cuphead the delicious last course bosses
Image Credit: Studio MDHR Entertainment Inc.

Not to be confused with Chef Salt Bae, Chef Saltbaker is a new Cuphead boss introduced alongside The Delicious Last Course. The chef is the final boss of the DLC so expect an appropriately difficult fight. Not just that but this has to be one of the most disturbing fights in the entire game; yes, even more disturbing than the Esther Winchester fight. Chef Saltbaker is pure evil and tortures defenseless foodstuff throughout the first phase while throwing everything at you except the kitchen sink. Things get even creepier from there, but I don’t want to spoil too much because this fight is worth experiencing for yourself.

1. Dr. Kahl’s Robot (Isle Three Boss)

hardest cuphead boss
Image Credit: Studio MDHR Entertainment Inc.

And last but certainly not least we have Dr. Kahl’s Robot, the hardest Cuphead boss in my opinion, even after the DLC bosses. In fact, this one is so difficult that it made our list of hardest video game bosses of all time. This aerial fight is absolute torture straight out the gate, to the point where phase two seems to have been made intentionally easy just to give you a bit of time to recover. But don’t worry because things ramp up again in phase three when the fight essentially turns into a bullet hell. All the aerial boss fights are difficult but this one is straight-up insane. Definitely give yourself a huge pat on the back if you manage to beat it.


  • Jason Moth

    I'm a classic jack-of-all-trades author who loves to write about most topics, though gaming has always been my strong suit. That said, I definitely won’t turn down the chance to cover some juicy news involving superhero movies, Stephen King novels, or space travel. Or robots. Or space-traveling superhero robots disguised as Stephen King.

Written by Jason Moth

I'm a classic jack-of-all-trades author who loves to write about most topics, though gaming has always been my strong suit. That said, I definitely won’t turn down the chance to cover some juicy news involving superhero movies, Stephen King novels, or space travel. Or robots. Or space-traveling superhero robots disguised as Stephen King.

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