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Techy Cutie Pony Collection!

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Description

Wonder how many people revved up their troll alarms when they saw that header.

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Background Pony #C399
But…what do you think ‘Derpy’ means? It’s from 4chan; what do you think it means?
Vree
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Not a Llama - Happy April Fools Day!
Magnificent Metadata Maniac - #1 Assistant
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Fine Arts - Two hundred uploads with a score of over a hundred (Safe/Suggestive)
The End wasn't The End - Found a new home after the great exodus of 2012

How does she get in to those posh events? Simple. Everypony loves Derpy.
 
A bouncer or attendant would see her and say “oh, if it isn’t Miss Derpy! (everypony knows Derpy) What a cute paperbag costume. You’re excited about your big night? Well, then it’d be rude to keep you up any further!” (stand aside while Derpy walks in happily pronking) “That does not apply to the rest of you, GET BACK IN LINE!”
Background Pony #8525
My headcanon states that Derpy lives outside of Ponyville and doesn’t have to pay taxes.
Background Pony #D835
The real retard is Snails.  
No, really. I think he actually might be developmentally disabled or something.
Background Pony #4A7C
Yeah…I’m gonna stick with my headcanon that she’s evil and only pretending to be stupid.
Mooncalf
The End wasn't The End - Found a new home after the great exodus of 2012

She didn’t volunteer to pay for repairs because Applejack volunteered first (possibly as a PR move to boost Sweet Apple Acres publicity) and she didn’t want to insult AJ’s generosity. And she doesn’t want to flaunt her wealth in case ponies start treating her differently.
 
Of course, AJ eventually failed to pony up the promised cash, and yet the hall was repaired later. Obviously, SOMEPONY financed it…
 
My personal headcanon is that Derpy is an excentric trendcatcher who works with, among others, Fancypants of Canterlot to scout talents in art and fashion, such as Rarity, so they can promote them into fame and make good money by being first in on all trends. Fancypants work the Canterlot circuit, she handles Ponyville because she’s more rurally minded. Derpy’s carefully designed “well-meaning klutz” persona allows her to attend all sorts of events without raising suspicion, whether it’s a welcoming party for Princess Celestia’s number one student moving to town, snooping around Fluttershy’s coop to spot the latest pegasus pet trends, or just hang out in wells to catch some juicy gossip. And working as a mailmare is a great way to establish social networks.
CottonTales
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
Wallet After Summer Sale -
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
Not a Llama - Happy April Fools Day!
An Artist Who Rocks - 100+ images under their artist tag
Artist -
The End wasn't The End - Found a new home after the great exodus of 2012

Ruler of Sheep
@Daniel  
I’m personally just chalking that up to Canon Discontinuity, it stopped being a problem because it was no longer relevant, but it’s no fun to analyze it that way I guess