Crazy Headcanons

Amphibian Swamp
Silly Pony - Celebrated the 13th anniversary of MLP:FIM, and 40 years of MLP!
Shimmering Smile - Celebrated the 10th anniversary of Equestria Girls!
Roseluck - Had their OC in the 2023 Derpibooru Collab.
King Sombra - Celebrated the 10th anniversary of The Crystal Empire!
A Lovely Nightmare Night - Celebrated the 12th anniversary of MLP:FIM!

Izzy, Sunny and Hitch like Mario games, Zipp and Pipp thinks Mario games are okay, Posey could care less, Dahlia isn’t interested in most of them, but she had payed some, Rocky likes them, Jazz isn’t really a fan of them/dislikes them
Posted Report
Twi Clown
Silly Pony - Celebrated the 13th anniversary of MLP:FIM, and 40 years of MLP!
Shimmering Smile - Celebrated the 10th anniversary of Equestria Girls!
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
King Sombra - Celebrated the 10th anniversary of The Crystal Empire!
A Lovely Nightmare Night - Celebrated the 12th anniversary of MLP:FIM!
Princess of Love - Extra special version for those who participated in the Canterlot Wedding 10th anniversary event by contributing art.
Elements of Harmony - Had an OC in the 2022 Community Collab
Non-Fungible Trixie -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
Verified Pegasus - Show us your gorgeous wings!

Übermensch in training
Twilight wanted to get back at Pinkie for some minor slight. So when no one was watching, she added raisins inside a pastry the pink pony was about to eat.
@Cosmas-the-Explorer
It was actually Rainbow Dash. You’d pick a daredevil but still cautious enough pony to handle those things, don’t you think?
Posted Report
Korora
Silly Pony - Celebrated the 13th anniversary of MLP:FIM, and 40 years of MLP!
Lunar Guardian - Earned a place among the ranks of the most loyal New Lunar Republic soldiers (April Fools 2023).
Non-Fungible Trixie -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
Verified Pegasus - Show us your gorgeous wings!
Preenhub - We all know what you were up to this evening~
Artist -
Ten years of changes - Celebrated the 10th anniversary of MLP:FiM!
The End wasn't The End - Found a new home after the great exodus of 2012

Let's keep calm here...
MLP Analysis: (Spoilers for a recent Jasper Pie comic)
The Rockville branch of the Pie family is incensed with Zircon Pie for abandoning Jasper with Uncle Fettucine and Aunt Cannelloni simply because Jasper embarrassed him. Even Marble has some very harsh words for him [Zircon].
Cosmas-the-Explorer
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
Notoriously Divine Tagger - Consistently uploads images above and beyond the minimum tag requirements. And/or additionally, bringing over the original description from the source if the image has one. Does NOT apply to the uploader adding several to a dozen tags after originally uploading with minimum to bare tagging.

Explorer in Training
I think I found Applejack’s jam.
Also I always envisioned Applejack having some Scottish heritage since a lot of lower class Southerners have those Scots Irish roots.
Posted Report
Cosmas-the-Explorer
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
Notoriously Divine Tagger - Consistently uploads images above and beyond the minimum tag requirements. And/or additionally, bringing over the original description from the source if the image has one. Does NOT apply to the uploader adding several to a dozen tags after originally uploading with minimum to bare tagging.

Explorer in Training
Twilight Sparkle comes from one of Canterlot’s First Families, Canterlot’s elite patricians. Her family is not as wealthy or influenctial as it uses to be, but she has a very blue bloodline and her family is still quite prosperous and well respected.
That being said Twilight is very humble and even lies sometimes to hide that fact. She has no interest in showing off her family’s lineage since she belives in serving others and treating others equally.
Posted Report
Amphibian Swamp
Silly Pony - Celebrated the 13th anniversary of MLP:FIM, and 40 years of MLP!
Shimmering Smile - Celebrated the 10th anniversary of Equestria Girls!
Roseluck - Had their OC in the 2023 Derpibooru Collab.
King Sombra - Celebrated the 10th anniversary of The Crystal Empire!
A Lovely Nightmare Night - Celebrated the 12th anniversary of MLP:FIM!

I randomly got this minor headcanon. It’s that… Rocky might be related to Zipp and Pipp. I’ll likely drop and forget this in a few days, but it’s interesting to think about.
I don’t mean by being their brother. He is a bit similar to Zipp in a few ways. But he doesn’t really look like Queen Haven or Pipp as much. So I assume he’s more likely to be their cousin if they’re related.
Well, depending what the dad looks like, he might be Zipp’s younger brother and Pipp’s older brother…
Korora
Silly Pony - Celebrated the 13th anniversary of MLP:FIM, and 40 years of MLP!
Lunar Guardian - Earned a place among the ranks of the most loyal New Lunar Republic soldiers (April Fools 2023).
Non-Fungible Trixie -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
Verified Pegasus - Show us your gorgeous wings!
Preenhub - We all know what you were up to this evening~
Artist -
Ten years of changes - Celebrated the 10th anniversary of MLP:FiM!
The End wasn't The End - Found a new home after the great exodus of 2012

Let's keep calm here...
Crystal War Timeline: Wind Rider was supposed to guard Seaddle, but made a foolish and insubordinate charge meant to garner glory for himself. He himself was mortally wounded, his command took heavy casualties (many KIA, many WIA, and many captured), and the token guard he left in Seaddle was insufficient to stop Sombra’s forces. Oh, and this was when Rainbow Dash lost her wing.
Background Pony #1071
Jazz’s full name might possibly be Jasmine Hooves. Jasmine is a type of flower and a type of rice, most earth ponies have plant/natural/whatever sounding names. She likely shortened it to Jazz Hooves because for the pun.
Cosmas-the-Explorer
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
Notoriously Divine Tagger - Consistently uploads images above and beyond the minimum tag requirements. And/or additionally, bringing over the original description from the source if the image has one. Does NOT apply to the uploader adding several to a dozen tags after originally uploading with minimum to bare tagging.

Explorer in Training
Granny Smith’s parents were border reivers, raiders from Trotland who were fierce guerilla fighters that raided Trottingham.
They moved to get away from their violent warmongering past. Although their fighting skills proved useful in defending Ponyville from Timberwolvws.
Posted Report
Cosmas-the-Explorer
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
Notoriously Divine Tagger - Consistently uploads images above and beyond the minimum tag requirements. And/or additionally, bringing over the original description from the source if the image has one. Does NOT apply to the uploader adding several to a dozen tags after originally uploading with minimum to bare tagging.

Explorer in Training
Rarity’s family used to be poor. Even Rarity as a filly had to contribute to making the family bits.
After Rarity’s boutique became a success in Ponyville, the Belle family lived in luxury.
Rarity prides herself in ensuring that her little sister would not have to work the same laborious jobs young Rarity had to and could focus more on her education. Rarity also pays for her parents to have vacations since she thinks they deserve it for raising her through tough times.
Elidiotadelaesquina
Shimmering Smile - Celebrated the 10th anniversary of Equestria Girls!
Lunar Guardian - Earned a place among the ranks of the most loyal New Lunar Republic soldiers (April Fools 2023).
Roseluck - Had their OC in the 2023 Derpibooru Collab.
Artist -

Stupid idiot
They moved to get away from their violent warmongering passt.
It’s like the old west.
Rarity’s family used to be poor.
That would explain his why he defends his convictions, by expanding beyond its Ponyville Boutique. And basically it would explain her behaving in the episode “sweet and elite”.
Posted Report
Korora
Silly Pony - Celebrated the 13th anniversary of MLP:FIM, and 40 years of MLP!
Lunar Guardian - Earned a place among the ranks of the most loyal New Lunar Republic soldiers (April Fools 2023).
Non-Fungible Trixie -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
Verified Pegasus - Show us your gorgeous wings!
Preenhub - We all know what you were up to this evening~
Artist -
Ten years of changes - Celebrated the 10th anniversary of MLP:FiM!
The End wasn't The End - Found a new home after the great exodus of 2012

Let's keep calm here...
In every Ponýmon game, the player character gaining a Pokéball cutie mark is a milestone in the story.
Posted Report
TheWAMBrony2021
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Non-Fungible Trixie -

Spitfire has Multiple Personality Disorder, which explains her personality change in Season 3 onwards, compared to her personality in the first 2 seasons.
Posted Report
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