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The Sky Kingdom's Disaster Master is indeed named "Cloudmaster".
Maybe Punisher Pumice is not THAT inaccurate after all [but still very inaccurate].
  • Jossed. It's actually Mistmaster.

Saturday and Parfait are related.
Their character designs are rather similar, at least from the waist up. Both Saturday and Parfait have pink(ish) hair parted on the side, upturned noses, a neck decoration, puffy bell-shaped sleeves, and arm-length gloves. If you squint, even their names are connected - a parfait is a bit like a sundae which sounds like Sunday which is the day after Saturday.
  • Saturday is from the Flower Kingdom, which makes this unlikely.

Azalea is the Flower Kingdom princess.
We have seen characters disappearing and memories of them disappearing. Who's to say that Azalea had her memories wiped of being princess? We know the contest is a fake, according to Peridot. Plus, the flower Nautilus is seen looking at in the dressing room looks like an azalea flower. Perhaps this was Azalea's closet and old clothes?
  • Confirmed.

Azalea is Rosemaster disguised
.The banner for p.598 shows Azalea with a rose reflected in her glasses and she was in the background for the duration of the story. She could slip out at any time no one would have notice if she was gone.
  • Jossed. Azalea is the Princess of the Flower Kingdom, and the reason that she has the roses was because she was being controlled by Rosemaster.

Rosemaster is the former princess turned Disaster Master of the Flower Kingdom.
The subtext between Nightmare Knight and Rosemaster seems indicative of romantic feelings, mostly one-sided. It's possible that Rosemaster was formerly the princess of the Flower Kingdom, who fell in love with the Nightmare Knight but signed the Dream Sword before finding out his true personality. Regretting her actions, she usurped the original Thornmaster and became Rosemaster. Nautilus' ancestor might have something to do with this back story, hence her hatred for the Princess. His comment of "I've learned Nothing" after speaking with Parfait may have alluded to when he first befriended Rosemaster when she was a princess.

The Nightmare Knight has tried to step out of his role in the past.
His "I've learned nothing" comment definitely seems to imply that something like his quasi-friendship with Parfait has happened before, and apparently did not go well. He definitely doesn't seem to want to go through the whole song-and-dance, and with this being the hundredth cycle it can't be the first time he's gotten tired of it. Time will tell if there is some outside force preventing him from doing this or if he's just had bad luck at past attempts.
  • This was pretty much confirmed in the middle of chapter 3, when the Nightmare Knight Flash Backs to a time when he tried to make peace with a previous legendary hero, named Calabash. Calabash rejects his peace offering saying it's "just a trick".
  • Confirmed.

Narrativium (or the in-universe equivalent) is heavily at play in this universe, and the "Good" side will always win.
Because honestly, Splashmaster may have been
incompetent, but Noisemaster, Mutemaster, and Rosemaster, and especially the Nightmare Knight himself, are intelligent/powerful enough that they should have won by now — Noisemaster actually would have won in-story, without the Knight's intervention. This is why the Dream Oracle is so apathetic — she knows she can be as unhelpful as she wants; her Legendary Hero will win no matter what she does. The Nightmare Knight also knows this, which is why he saved Trebleopolis (why throw innocent lives away for a lost cause?), why he seemed so sad at Rosemaster's Determinator declaration, and why he reacted so badly to Cordelia's criticism (because it's annoying to be told how to do your job better when you know it's doomed to fail no matter how well you do). The current heroes may or may not figure this out and be on their way to breaking the usual story's cycle.

The Nightmare Knight wasn't actually referring to Nautilus when he mentioned a threat in the party; he meant Liquus.
Consider the fact that Liquus electrifying Splashmaster is the main reason Almond was able to slice him up so easily, and the barrier Liquus made saved Nautilus and indirectly defeated both Noisemaster and Mutemaster. Maybe Liquus proves a threat to Rosemaster as well?
  • Jossed; Rosemaster doesn't seem to care about Liquus at all.
The Nightmare Knight is being "evil" for show; the Oracle might be the true villain.
The Nightmare Knight, despite his appearance and demeanor, doesn't seem too bad. Sure, he's decimated a few places using the Disaster Masters, but he seems to care about the heroes. He let the gang through the Intermezzo Wall, he was likely the one who stopped the Noise Blaster, and he (accidentally) spends his free time helping Princess Parfait and listening to her problems.The Oracle, on the other hand, doesn't care. She forgets everyone's names, uses Chardonnay to clean toilets, and most of the "nice" things she's ever said were complete lies. She didn't even put effort in hiding the Disaster Stones.My guess is that the Oracle is using the Nightmare Knight to make her seem like a powerful and benevolent guide of sorts. The Knight causes mayhem for her; she hires heroes to capture him, and years later he's released once more, like clockwork. It keeps the bunny people grateful and willing to follow her.But things are different this time; the hero's a weakling, his sister won't sit still and be kidnapped, and even the Knight's slipping up by befriending those he's supposed to fight. Somehow, this will cause the whole system to fall apart, and the Oracle will NOT be happy with any of them.
  • To further this, the Disaster Masters are not in on this deal, and in fact the Nightmare Knight himself isn't aware of the Dream Oracle's interference and is just resigning himself to his reputation. Perhaps he had tried previously to do good, or he was the original guardian of Dreamside, but after so many years he's completely forgotten his original intentions and just goes along with it.
    • Not necessarily: He did try to take over Dreamside the first time, but started to feel empathy for it after his first defeat. He stayed in his role because of a combination of all of the expectations people like Calabash and even his own minions put upon him as the Nightmare Knight, and the fact that his powers run on fear, and all of his beloved minions would die if he was defeated for good. Furthermore, when the Oracle visited Cabbage when he was younger, she looked upset that the Knight wasn't actually summoned. Not even angry, just sullen. She might not be the nicest person around, but there has to be a reason for her to look like that if she was intentionally making everyone suffer.

When the time comes Princess Parfait will refuse to sign the dream sword to seal away the Nightmare Knight
Princess Parfait seems to see some good inside the Nightmare Knight, and sincerely cares about him as a friend. She wouldn't want anything bad to happen to him. Plus she's likely to be the last princess they have to ask to sign the dream sword, and if she refused to sign it that would force the heroes to come up with some different resolution than sealing him away.
  • Perhaps she will refuse... but then Peridot will fill in as a substitute.

The Nightmare Knight will help (or allow) Parfait to escape the Caketown Castle.
A guess based on the interlude title picture. Parfait is shadowed in purple, making a "ssh" gesture, and surrounded by purple stars.
  • Jossed. The opposite happened.

Parfait will fall for The Nightmare Knight, or vice versa.
Face it, he's much more interesting than Carrot. Parfait and The Nightmare Knight also seem to be two of the saner characters in the comic, and he's already helped her out once. And look at the wallpaper for the current interlude - pink hearts and purple stars!
  • Combined with the wmg above the one above this one: Cucumber and co. will finally get back to the Doughnut Kingdom with one more signature to go: Princess Parfait's. However, by that time she will have fallen in love with the Nightmare Knight, and not want to seal him away. This will force the Cucompany to find a peaceful resolution, breaking the summon-fight-seal cycle.

Lettuce will help Parfait escape Caketown Castle
Lettuce is known to have a crush on Tomato. She'll help Parfait leave so she's out of the way thinking if Parfait is gone she'll be able to get Tomato to give her the kind of attention he gives Parfait.

The Nightmare Knight created the barrier.
Purple stars are his thing, after all. Noisemaster knows this, which is why he just gave up. Which also explains the "So, it's like that" callback.
  • It's been confirmed on Gigi's twitter that anything purple and sparkly is an effect of the Nightmare Knight's magic which would include the barrier. Him saving Trebleopolis, and Dream Oracle lying and taking the credit for it has been lampshaded enough in the comic and talked about on twitter that it should be considered canon by this point.

Cosmo created the Noiseblaster, AND the barrier that stops it
Noisemaster's smart, but he's not been shown to be good enough with machines to make the noiseblaster on his own. Unless a character who hasn't been introduced yet did it, Cosmo is the only tech-smart character we've seen that could help him make the Noiseblaster. But Cosmo's also a really sneaky kid. It's likely they're Playing Both Sides and sold the tech for the barrier to the people of Trebleopolis to make a profit off of both Noisemaster and the innocent citizens he was going to destroy. Cosmo probably got the idea to exploit the whole legendary hero thing for profit when they learned about it from Almond in Caketown.
  • The barrier half of this has been Jossed. The Nightmare Knight did that.
  • However, the Noiseblaster is looking increasingly likely. Cosmo seems to be working for "Glitch—-," the character first shown here. Since "Glitch" seems to be behind the Noiseblaster to some degree, it's very likely that Cosmo is as well. Plus, there was a Word of God somewhere that Noisemaster had gotten help building the Noiseblaster.

Cosmo is a Disaster Master in disguise.
Specifically, they'll be the one encountered in the Space Kingdom, due to the star pattern on their coat. It's entirely possible that they used their mad scientist skills to create some sort of cloaking device and is pretending to be a citizen. Furthermore, they appear immediately after the scene in which the Nightmare Knight is resurrected (and seven beams of light shoot from the castle, most likely releasing the Disaster Masters). Presumably, they're the most capable of the Knight's servants, and is out to foil the heroes through use of Obfuscating Stupidity - their inventions have always 'malfunctioned' in ways that could have killed them if they weren't lucky, and always while they were attempting to travel to another kingdom.
  • All those question marks on their stat sheet are rather suspicious...
  • Furthermore, it seems likely that the Space Kingdom's Disaster Master is the one represented by the Disaster Stone with a power symbol on it. That would be a pretty suitable symbol for a Disaster Master who works with technology.
  • The "Disaster Master in disguise theory" is Jossed. These three pages show Cosmo working with a Disaster Master, not as a Disaster Master.

The Nightmare Knight and the Oracle are siblings
Just a hunch.

“Queen” Cordelia is the Space Kingdom princess.
We know there's a Space Kingdom. It may not be on the map – at least, not the one in Saturday's tower – but where else do spaceships come from? Queen Cymbal even mentioned it once. Cordelia constantly hints that she's from Space Kingdom. She rants about what she'll do to this planet, how she'll take over this planet, how this planet shall bow down to her, etc. etc. She has those “weird ears” similar to COMMANDER CABOODLE, CHAMPION OF JUSTICE! (Who, interestingly enough, seems to know about her evil scheming. The main characters wouldn't have found out if not for Lord Cabbage and the Dream Oracle...) Her color scheme also fits the disaster stone that bears the power symbol. Whether she's a princess or not is just a guess, but this troper thinks it would add to her character a great deal. Plus, when Nightmare Knight inevitably betrays her, she and Peridot can (begrudgingly) join the heroes' side.
  • No, her ears aren't right. The first book has a page talking about how you can tell where each person is from based on their ears. Space Kingdom bunnies have wide ears with a symbol inside, like Cosmo. The Space Kingdom (on the moon) is still considered part of Dreamside, the whole world. The same ear page also says "If they've got cat ears or something, like Cordelia, they probably aren't from Dreamside."

Saturday is the Flower Kingdom princess.
Her ears have sprouts on them, indicating she's from the Flower Kingdom. The first book says that the Flower Kingdom is known to some as "a land of dangerous ruins for intrepid adventurers to explore!" Such a place might inspire an adventurous princess. And besides, what kind of thief has a butler? One that's a runaway princess with a royal servant. Also, Cucumber's reaction would be funny, which is a good enough reason for this series.
  • Looks pretty unlikely at this point, since Azalea was confirmed to be the Flower Kingdom princess. Unless she happened to have a renegade sister, which is unlikely.
  • Actually confirmed! Saturday and Azalea are the same person. And Cucumber's reaction was indeed funny.

Noisemaster and Legato are Co-Dragons, conspiring to overthrow the Nightmare Knight.
It's been theorized that Legato is working for or in conjunction with Noisemaster for several reasons: two of the tentative Disaster Stone designs seem to match them perfectly; what looks like Legato's speech bubble color shows up in Noisemaster's broadcast from Rhythm Ridge; Noisemaster talks about scheming with an unseen partner-in-crime; and legato, or "tied together", refers to smooth transitions between notes in music. It's possible that these two could actually have ambitions of their own. Consider that...
  • The Nightmare Knight and the Disaster Masters have been summoned and defeated 100 times, and a common fan interpretation of the NK himself (which recently gained support from the page where he blasts open a wall obstructing Cucumber's group) is that he's secretly helping the heroes because he wants the cycle to end. Noisemaster might have a similar motive, in that he blames the NK for their failures and wants to take matters into his own hands.
    • Noisemaster was briefly shown to act darker and more cunning when the NK wasn't around. His Totally Radical schtick is to keep suspicion off of him. When he told the NK that his scheme would "put ya in the hospital", it wasn't just a figure of speech.
Most likely, Noisemaster and Legato plan to turn the Noiseblaster on the Nightmare Knight once it's fully-charged. A laser that can take out a whole kingdom could do some serious damage to the final boss. Finally, the Nightmare Knight might actually be expecting this ( especially if it's happened before), which is why he wants Cucumber and friends to reach Noisemaster and defeat him.

Legato and Noisemaster being Co-Dragons has been Jossed, although still waiting to see whether or not Noisemaster is planning a betrayal.

Also, the Noiseblaster can be powered up with the screams of the princesses (or just ordinary people, too).
Think the Scream Extractor from Monsters, Inc., and we know Princess Piano is pretty much the loudest character in the comic so far. It's also why Legato is so gleeful over finding Nautilus, because it means they can power it up even faster now. (Second part Jossed for now, but might still come back.)
  • First part is confirmed, however.

Noisemaster and Legato are somehow related to the king on the other side of Intermezzo Wall.
Lute referred to Legato as a sorcerer and said that he was at least a century old (we don't know how long the wall has been up, but the Melody Kingdom does have rumors about it being full of ghosts on the other side), so he could've been the king's magician. If Noisemaster didn't have anything to do with the aforementioned rumors by just wreaking havoc over there, he might actually be the other king; he made some sort of deal for power with the Nightmare Knight to get revenge on the rest of the Melody Kingdom.
  • Furthermore, the Nightmare Knight specifically says he can't believe Noisemaster "is still talking like this", implying at some point he did an overhaul of his style.

Cucumber will break the cycle of the Legendary Hero once and for all.
Most of the other characters have been stealing the spotlight, but eventually his character arc will end in a lesson about how there are multiple ways to be a hero (or that nobody HAS to follow the genre 'rules') when his extensive magical studies allow him to stop the Nightmare Knight and Disaster Masters from being brought back every 5,000 years. The Nightmare Knight might even be redeemed.

Legato is some kind of ghost.
Not a whole lot to say, but he does have strange powers, still looks young despite being "an ancient evil", and he might have some kind of unfinished business or mental block keeping him from passing on to the other side.
  • Jossed. While interrupted, one of the ghost instruments said the Legato in the comic is different from the one from the legends.
    • Although it's been revealed that he put at least a fragment of his powers and personality into Panpipe's contact lens.

Almond and Peridot will get together in the end
They both seem have crushes on each other, due to how often they end up helping each other out. Either that, or Peridot's love is unrequited.

Legato's contact lens will reappear later on.

X will officially ally with the Cuquistadors sometime before the end.
  • Commander Caboodle
  • Saturday
  • Peridot
  • Count Legato (Either Panpipe, or a third one)
  • Princess Piano
  • Bacon (Just covering all the bases here)

The "Borrowed wand" is actually a legendary artifact
...Thus explaining why it can meld with the Disaster Stones.
  • Jossed. Turns out it was just a TV show prop.
  • Not Jossed? This seems to be in reference to the wand Cucumber got from Saturday's treasure hoard, not the Pumice one.

Noisemaster's Noiseblaster was blocked by either the Space Kingdom Disaster Master or The Nightmare Knight.
If the former, it's so that Cucumber and Co would have a chance at still beating Noisemaster so he can fight them himself. If it's the later, it's because it was a plan that not even The Nightmare Knight would have approved of or he has a code against wholesale slaughter of innocents. When Noisemaster had a plan that was "So ill, it'll put you in a hospital", he might have been literal, a plan that Nightmare Knight wouldn't be able to stomach.

The Noiseblaster was blocked thanks to assistance from the Space Kingdom
When they said that Princess Piano's screams reached even the Space kingdom, this was not Hyperbole. Somehow, they were able to figure out that this time wasn't a case of Crying Wolf, and they sent someone to help.
  • Jossed.

Cucumber will turn against the Dream Oracle soon.
The ending of chapter 2 shows that his objections to her behavior are getting much stronger and worse, and the ending picture shows him cast in a darker light. The question is whether this would actually qualify as a Face–Heel Turn or not...

Cucumber quest has started a Deconstruction arc, but will eventually wrap around to a Reconstruction again.

The one who will ultimately end the cycle...
... is none other than Nautillus.

Face it- Cucumber doesn't want to be the legendary hero, and Almond is fully willing, but it's Nautillus that has been given a bit of specific focus over the past few chapters- she did the most during chapter 1, and it's specifically her that is able to deal with Noisemaster last. The story could likely set itself up or subvert both the expectations that wither Cuco or Almond will break the pattern on their adventure by having her find a way in their stead.

The Disaster Master of the Flower Kingdom will be named Weed Master.
So far, all of the revealed Disaster Master has this inverse relationship to the kingdoms they are sent to. A large Splash versus a gentle Ripple. Noise and Mute(ness) versus Music. What better way to oppose gentle flowers than with nasty weeds that choke the life out of other plants? On that note, if the Space Kingdom is high technology, their Disaster Master will be Glitch Master. Perhaps he had an early cameo here?
  • Jossed, it's Rosemaster. However, the "inverse naming" theory is sort of confirmed, as she was originally called Thornmaster (as in "every flower has its thorns").

Queen Cordelia and the Nightmare Knight will go their separate ways soon, one way or another.
Either Cordelia will switch to using alien technology and turn out to be Eviler Than Thou, or the Nightmare Knight will take over fully after getting tired of Cordelia's attitude.
  • Unlikely, as of 824-828. After all, they share a common weakness.

Peridot is helping Cordelia not just For the Evulz
My guess is that Peridot didn't exactly have a great past. She's seems to be a sort-of perfectionist magician who freaks out at failing at anything, and acts high and mighty to cope with the stress, but she doesn't really have any friends because of her attitude. However, when Cordelia came along, she was the first person to actually care about Peridot, and even makes her feel appreciated and comforted despite any mistakes she makes. To Peridot, she wants to make it up to Cordelia by being her number one minion that Cordelia can rely on.
  • Confirmed, though the exact details of Peridot's past are unconfirmed.

Caboodle is related to Cordelia in some way and wants to bring her back to their home planet.
We already know the the "Queen" is a cat in a world full of rabbits, perhaps she had her own spaceship and it crash landed and without any other idea on how to get home she decided to make a living on Dreamside by trying to dominate this strange bunny land. Caboodle is off to try and find Cordelia before she causes much more madness than she already has and bring her back where she truly belongs but it has been a bit of trouble on the way. As for their relation I would either say a sibling, cousin, or her crazy husband who is way into being a space warrior.

The legendary hero isn't just meant to defeat the Nightmare Knight. He's also meant to take his place.
Taking into account the Nightmare Knight's jaded attitude, how he's doing everything like he's going through the motions to the point of almost looking tired of it, like he's acting out a role in a play he hates. Consider how he straight up saved the Melody Kingdom when it came into real danger, or even how he actively helped Cucumber past the magical locked door. Consider their surprisingly similar personalities, and how Cucumber showed instant proficiency in using the magic of the disaster stones. It's not impossible the Nightmare Knight was the previous hero, having defeated his predecessor and forced into taking the mantle, just as his predecessor had. He may be jaded because he knows Cucumber will succeed, only to be become the next Nightmare Knight and continue the cycle.
  • Jossed; NK's backstory (in Interlude 3) shows that he and the Legendary Heroes are different people, and that the heroes do not take his place.

The Space Kingdom's Disaster Master will be named Glitch Master
This is in keeping with the noted 'inversion' of the names of the Masters in regards to the Kingdoms they terrorize. It would also fit, as for a Kingdom that is almost certainly highly dependent on technology, some sort of rogue, malevolent AI or Anti-Tech being would be absolutely terrifying.
  • On top of that, Cosmo - all but explicitly said to be Space Kingdom - comes close to saying it here right as... something teleports them away. Complete with dead pixels and artifacting!
  • Seems to be confirmed. Glitch—- is indeed Glitchmaster, and Gigi has all but outright straight up said to my knowledge that she is the Space Kingdom's Disaster Master.

Glitchmaster is The Man Behind the Man
  • Seems to be pretty thoroughly Jossed.

Cosmo is both Glitchmaster AND the Space Kingdom Princess.
How else would a 'glitch' exist but as a malfunction in something else? In this case, inside the system of an otherwise only slightly eccentric, techno-savvy princess... who seems to have constant problems with their otherwise fine inventions constantly 'glitching'.

(Cosmo's gender is never specified)

  • The former is Jossed, since pages 714-716 show that Cosmo is working *with* Glitchmaster.

"Glitchmaster" is the original Nightmare Knight, and created the current one in his image.
The hologram form of Nightmare Knight is actually his true form, and Nightmare Knight seems too nice to be the real main villain. Since "Glitchmaster" is so far the most ruthless character shown, working on the Noise Blaster, his interaction with the heroes in the most recent pages, possibly having an Evil Plan to "annihilate" Dreamside, it's possible that HE was the Nightmare Knight that "brought destruction" all those years ago, as that seems more in character with him as opposed to the actual Nightmare Knight. Maybe Nightmare Knight is another Disaster Master, one who's designed to look like the main villain as a decoy.

Also the Moon seems like a much more appropriate place for a final battle than some castle in the middle of a candy town.

Glitch——- isn't actually a Disaster Master
It's possible- why else would the static cut off what WOULD have been the "Master" in his name? Relating to the above, maybe it's "Glitch Knight"?

Caboodle will join the party
His ship was blown up, all he (might) have is the clothes on his back, he considered Cucumber and co to be FELLOW ALLIES OF JUSTICE, and he's on the title page of Chapter 3. Need I say more?

Cosmo is the Space Princess or, if Cosmo is a boy, Prince
  • Cosmo's gender hasn't really been specified. The reason why s/he isn't in the Space Kingdom is because s/he is in Dreamside, trying to escape the dastardly Glitchmaster (Mentioned here, as Glitch----). Another great twist would be for Cosmo to be a boy-making him a Prince-which would create a whole new set of problems stemming from how there is no princess, a princess needs to sign the sword, etc.

Cucumber and Perido-.... Perridoh....will have an Accidental Kiss.
I'm sorry, I just really wanna see this.

The reason why Almond can shove her sword in deep in her pockets....
Is because it's actually a magic coat that she got from one of her adventures.
  • But Almond's never been to an adventure before...?

The reason why everyone is CONSTANTLY forcing for Cucumber to be a hero is because....
It's just tradition for their family. And the only reason his farther sent Cucumber on a quest is to make their family look good. Even the little green fairy thing is in on it, which is why the orbs are always so badly hidden. It is also why Nightmare Knight isn't really "evil" (from my perspective anyway) and just Lawful Neutral. He is bored and tired from being resurrected from villains who always want to take over the world and then being eventually and predictabally, beaten by The Hero. Even the villains know about this and are just being evil because they are bored.

The Dream Oracle's third eye shows her real emotions and intentions, despite what she says/her face is expressing.
Cucumber will visit his school when they get to Sky Kingdom.
It's pretty much inevitable.
nightmare_child_35 will make an appearance.
Because why. The fuck. Not.

The real reason Nautilus was captured
Is because she would be able to contradict the story of the flower royal family's fall. Nautilus knows all the other princesses personally. If the flower kingdom really didn't have one, she would have been the first (or second) to point it out. Instead, her response was cut off by a scene change to Rosemaster, and she was captured offscreen.Of course, "Every one of it's citizens knew Botanica Springs had no royalty," but Rosemaster has shown the ability to remove people from the memories of others, and she's been active for a while now.Mr. R is a part of the plan, and knows it. Cabbage doesn't, because he didn't ask questions aside from his salary.

Mr. R is Rosemaster in disguise.
We already know that Rosemaster is a "master" of fashion and beauty. It's been implied that she was able to transform herself once already, to transition to her correct gender (female). Their character designs have several subtle similarities: the pale green skin, the brightly-colored triangular nose with matching floral hair, the partly obscured eyes. They have similar behavior patterns, too (genteel elegance with occasional bursts of disapproving menace). Rosemaster's mysterious "accessory" looks similar to Mr. R's hairstyle. And most significantly, note "his" name. What exactly does that "R" stand for? It stands to reason that Rosemaster could have used her memory-altering powers to convince the Flower Kingdom citizenry that [A] they had no royalty, and [B] they'd always been fans of Mr. R and "his" magazine, thereby allowing her to set up a trap for the hero's party. And perhaps the "threat" that Nautilus posed was her ability to recognize Rosemaster's pre-transition appearance ("Thornmaster"), due to her history lessons? It's convoluted, for sure, but that's exactly what the Nightmare Knight pointed out from the beginning. And the stress and dysphoria of using her pre-transition body as a disguise would help explain Rosemaster's growing unhappiness.
  • Corollary: "Mr. R" constantly wears sunglasses to disguise the red color of her eyes. When we first met Rosemaster, nearly every frame showed her standing in front of a mirror, with her reflection. Maybe she's using a magical doppelganger?
  • Jossed, Mr. R is actually Brambleby.

Cosmo is an independent part of Glitchmaster
This has been mentioned before, but it's most likely that the "Glitch—" mentioned here is Glitchmaster. Cosmo seemed to dissolve when Glitchmaster, disguised as the Nightmare Night, appeared in their place. I'd guess that Cosmo is a part of Glitchmaster that can act independently, but only at Glitchmaster's whims. If she is sick of their antics while they are in 'contol', they can simply absorb Cosmo back into... whatever Glitchmaster even is. It's also possible that Cosmo is what Glitchmaster originally was before becoming a Disaster Master, if the Disaster Masters had any identity beforehand. Cosmo will end up overpowering Glitchmaster's control in order to give the heroes a chance at actually defeating her, since- from what we've seen so far- she is overwhelmingly powerful when unchecked.

The Guardener is actually just a normal denizen of Dreamside
The Nightmare Face she showed to the gang is just an illusion (or perhaps a plant-induced hallucination) s/he uses to scare away intruders. It might also be how s/he managed to run off Rosemaster the first time she went for the Hocus Crocus.
  • Jossed. As of Intermission 4, the Guardener's appearance seems to be just how they look.
The rulers of the Flower Kingdom are Sunflower and Aster.
For a bonus, they'll both be men.
  • Confirmed!

Glitchmaster is the one deleting memories from people
.Rosemaster has no sign of being able to control memories, but Glitchmaster is a computer related villain, which means he potentially could affect memories. He needs Rosemaster to betray the Nightmare Knight, so assisting her by making sure no one would try and rescue Nautilus and Caboodle, then doing the same with everyone's memories of Peridot so Cordelia would not take anything Peridot said seriously if she were to escape, thus making sure the Nightmare Knight never caught wind of their plan.
  • Jossed; Rosemaster is the one who manipulated everyone's memories, using flowers that bear their names (that's why there are bubbled flowers in the dungeon). Nautilus, Caboodle and Peridot are not named after flowers, so they're captured by the Roselings beforehand. Also, Aster here explicitly stated that the whole memory-erasing mess is Rose's doing.

Almond will meet Punisher Pumice in the Crystal Kingdom...
...But she will be extremely arrogant to her, causing Almond to rethink her idol worship and go through some character development.

Chapter 3 will end with the party radically shifted around.
Any of the following could happen to cause this.
  • Almond will remain brainwashed, stuck on the villain side with Glitchmaster (or maybe Peridot) pulling the strings.
  • Peridot will be stuck with the heroes, as the remaining Disaster Masters intend to punish her for the defeat of Rosemaster. Alternatively, she thinks Cucumber is her best chance to get the old Almond back.
  • Commander Caboodle: Sticks with the Cuqistadors. Where else is he going to go?
  • Carrot: Could discover something in Parfait's letter that leads him to return to Caketown
  • Cucumber: Takes Peridot's place on the evil side, planning to use this position to find out what the villains really want. He trusts Almond to keep his intended quest on track without him. (As such, this is incompatible with the first bullet)
    • Almond has been freed from the brainwashing and the Nightmare Knight had teleported Peridot so... Jossed

The Nightmare Knight is in direct contact with The Oracle and her group, going by the name Cabernet.
We already have reason to believe the continued cycle is in place for multiple reasons or one important reason, as demonstrated by the Oracle's hesitation on the subject and the Knight outright saying it isn't as simple as making peace with the heroes. Further, we see Chardonnay (The Oracle's spritely assistant) outright name Cabernet in purple text as someone who is knowledgeable on what we can expect. This page in of itself should be a big hint. Purple text on the one character who we know has a purple theme. We believe the Knight to be ultimately for continuing the cycle since he stops the Noise Blaster (regardless of his actual intentions.) Since we know the Nightmare Knight didn't know about the Noise Blaster, he can still fit this criteria. Lastly, in a series all about theme naming and the like, giving the name "Cabernet" to a character close to "Chardonney" implies they have similar background. Aged like fine wine?

The Crystal Kingdom has been destroyed.
Just a hunch.
  • Jossed; the kingdom and its royalty are totally fine. However, the kingdom is actually divided into two parts (the ice lands and the lava lands), and we haven't seen the latter part yet...

Glitchmaster's Plan
Is to usurp the Nightmare Knight and take his place. Glitchmaster has made her ambitions clear to Rosemaster, and the final step will be in the Space Kingdom, where the NK will be on hand to assist in Glitchmaster's defeat. But Glitchmaster will be waiting for him, and will spring a trap to destroy him. Then Glitchmaster will take over as the NK and ruler of Dreamside, possibly even installing new Disaster Masters in each Kingdom.
  • The Guardener will terrorize the Flower Kingdom.
  • Legato will haunt the Melody Kingdom with terrible musicals for all eternity.
  • Corrupt Bubblebeard, and all of the Ripple Kingdom will weep.
  • And the Doughnut Kingdom will be tyrannically ruled by... Cabbage.

The Dream Oracle is also an Emotion Eater like the Nightmare Knight
She feeds off of hope. She once held genuine power, but as she has increasingly caught on to the Nightmare Knight's true motivations, she has grown increasingly negligent and is now only using him and the legend to maintain her power. But because she has grown too jaded to do a good job, she is no longer inspiring hope, causing her to become weak. And it happened gradually enough for her to not completely notice what she is doing wrong.

This is all a dream.
Specifically, *Cordelia*'s dream.

I mean, having it called Dreamside is not merely for show, and it's significant that everyone has names that are things or occupations, EXCEPT Cordelia whose name is just a name, and whose role in the story is ironically the opposite of her Shakespearean version.

Perhaps the events of the story are her dealing with her real life issues, with the different characters aspects of her personality, named after food she likes, gems she loves, her favourite day of the week, etc etc....

Cordelia is a vampire.
She has fangs, is usually seen drinking from a glass of red stuff, and disappears at night on unspecified "evil business". In pages 710-11, sneaking back into the castle after said "business", she's seen carrying a small bundle, much like Count Dracula and Lucy from Bram Stoker's Dracula.

Saturday's plan has always been to steal the Hero's Journey for herself.
It's been implied from the start that she became a thief for the excitement. And what could be more exciting than being a legendary hero? And now that she knows how the Dream Sword works, she might actually be capable of doing it. It won't happen, but she could.

The next kingdom the gang will be going to will be the Sky Kingdom.
Based off what we've seen of presumably the next Disaster Master, he seems It looks like a better fit for the Sky Kingdom than the Crystal Kingdom.

The Disaster Master of the Crystal Kingdom will not be the main villain of Chapter 4.
The title of Chapter 4 is "Mismastered", and Peridot says to Cordelia if she "reads that book, we win". Also, Gigi has tweeted that "this chapter will change everything". It seems likely that either Cordelia or a Disaster Master from another kingdom will be the main threat.

The Oracle has been modifying everyone's memories
The Nightmare Knight has come back over one hundred times, and his disaster masters have caused trouble among large numbers of important people each time. And yet, this is apparently news to everyone aside from the Nightmare Knight and the Dream Oracle's servants, with everyone else only remembering the first time he showed up. Perhaps at the end of each cycle, the Dream Oracle uses that mysterious Wand with a magnified version of Rosemaster's power to erase everyone's memories so as to get a clean reset each time and ensure no one notices a pattern that needs to be thwarted.

Glitchmaster will become the true villain
It seems like NK is going to be redeemed, and Glitchmaster seems like the only real threat besides him. Bonus points if she tries to destroy/corrupt the world!

Steve will turn out to be Faux Affably Evil.
We're on strip 811 as of this writing. Steve seems to be the exact opposite of the Nightmare Knight, so since Nighty seems imposing but is actually tragic, maybe Steve's seemingly friendly behavior is just a facade. Maybe that's why Thebestmaster is afraid of him! Look how Steve's smile falters in the last panel. Maybe he's just trying to reassure Thebestmaster, but maybe he's going to fly into a rage in the next strip.
  • At least partially jossed, Steve's friendliness to Thebestmaster seems genuine. It remains to be seen how he'll act towards the heroes, but at this point this theory seems unlikely.

Steve is a Flawed Prototype.
It's very odd that both Thebestmaster AND Steve were apparently sealed. And one had to be released before the other could be released. It's stated that the Nightmare Knight we know never had a childhood, which means he didn't came into the world by natural means (i.e. being born). Whatever powers that be that created the Nightmare Knight also created Steve, but he just wasn't villainous enough to be a real threat and his own Disaster Master, Besty, was also subpar. This might be why he was sealed, because he was too weak for the job.

Steve and Nightmare Knight are two halves of a Literal Split Personality.
Steve is the fun side and Nightmare Knight is the fear side (since Steve is a more legit name, that was probably the name of the original). The two each went on to create their Masters, likely using a similar but fundamentally different method than the personality split did. It's also likely that NK sealed away Steve and Besty so that no one would see them and stop fearing him (so the Forsaken Master being the most terrible Master wasn't from the world's perspective but from NK's). He just decided to let Besty out this time because he is slowly accepting that it's okay for him to not be feared by everyone.
  • As a side note, it's likely that NK, after sealing away Steve in Drain World, impersonated Steve and tried to get Besty to be scary; when that proved impossible, he just sealed Besty away too.
  • As was pointed out on Tumblr relatively recently, the depiction of the Nightmare Knight on Punisher Pumice has two sets of horn-like projections on the sides: one set that has a hard angle like the Nightmare Knight's, and one that's curved like Steve's.

The cloud-like Disaster Master...
...seen here, is not Quakemaster, and they are not in the Crystal Kingdom. Instead, they reign over the Sky Kingdom. Going by the "inverse naming" theory, their name would be "Stormmaster" or something like that.

Steve is from the rumored alternate universe accessable from the Donut Kingdom.
In the first book, the map of the Donut Kingdom shows the strange platform in the middle of it. The flavor text mentions that it's rumored to be a portal to an "alternate world" of Dreamside. The platform itself is noticeably the kind of purple associated with the Nightmare Knight, and Besty outright mentions a "portal" on page 813. Steve seems to be the outright opposite of the NK, from being shorter and skinny to outwardly nicer, possibly indicating he's an alternate counterpart.

Near or during the final battle, Cucumber and co. will be cheered on by their allies from previous chapters.
Gigi's already had a lot of inspiration from TTYD, so why not add in something inspired from that and would likely cause Cucumber to embrace his role as not the Legendary Hero, but as someone fighting for Dreamside as a whole. The Power of Friendship would fit in a comic like this anyway.

Peridot was the one who told Cordelia of the Nightmare Knight myth, and tried to summon him first.
We see Peridot crying and surrounded by orbs when Cordelia reminisces on how they met. These could be what she believed were the dream stones, and attempted to summon the Nightmare Knight for whatever reason; when they didn't work and/or a space ship landed right in front of her, she broke down crying and Cordelia took pity.

Pumice has Cucumber's wand.
Just a hunch.
  • Possibly Jossed; this page implied that Cucumber got his wand back from the wand cleaners themselves.

Pumice will turn out to be a Nice Character, Mean Actor, resulting in a Broken Pedestal for Peridot.
Maybe it's a little too predictable, but it could end with Peridot telling the Nightmare Knight something like "You're my real hero", which would be freakin' adorable.
  • Jossed. The actress who played Pumice, Tephra, is actually really nice.

Princess Piano and Princess Ametrine will soon become lovers, or they already are.
In this page, Piano blushes upon mentioning Ametrine (or "Ammie" as she calls her), and one of the Q&A bits show that their friendship goes way back.

Also, it's hard to notice, but you can see that Ametrine is wearing a 'f' necklace, similar to Piano's 'p' necklace. It's very likely that the 'f' stands for 'forte' (a musical term meaning 'loudly'), since the 'p' in Piano's necklace stands for her name ('piano', besides meaning the instrument, is also a musical term meaning 'softly' or 'quietly'; yes, it's an Ironic Name). It's possible that the matching necklaces is a symbol of their friendship, or maybe even their romantic love for each other.

The Dream Oracle knows about the Nightmare Knight's Heel–Face Turn.
  • And that's why she is so negligent. She knows that she doesn't need to put in any actual effort. She can just goof around all she wants, and the Nightmare Knight will still be defeated and the cycle preserved. As for why she has never tried to break the cycle? It's the same reason the Nightmare Knight can't. She draws power from the myths of the Legendary Hero defeating the Nightmare, so breaking the cycle would break her power.

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