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DrizzieDoodles
Magnificence - Artist with 100+ Safe/Suggestive images with over 100 upvotes, and 5+ Questionable/Explicit images with over 350 upvotes
Ten years of changes - Celebrated the 10th anniversary of MLP:FiM!
Silver Bit -
Emerald -
A Really Classy Artist - 250+ images under their artist tag
Happy Derpy! - For Patreon supporters
Bronze Supporter - Bronze Patron
Hard Work - Merited Perfect Pony Plot Provider badge with only their own art
Perfect Pony Plot Provider - Uploader of 10+ images with 350 upvotes or more (Questionable/Explicit)
The Power of Love - Given to a publicly verified artist with an image under their artist’s tag that has reached 1000 upvotes

@Trahzo  
I prefer to think of it more along the lines of she gives her students someone to work with and instruct; after all it is a school for only the most gifted unicorns, so Celestia is expecting the students to be highly successful. Why not give them a chance to learn leadership and teaching skills early on? :3
VermiIIion
My Little Pony - 1992 Edition
A Really Hyper Artist - 500+ images under their artist tag
Friendship, Art, and Magic (2017) - Celebrated Derpibooru's five year anniversary with friends.
A Really Classy Artist - 250+ images under their artist tag
An Artist Who Rocks - 100+ images under their artist tag
Artist -

Cool! Fits right into my idea as Dim being Sunset’s former assistant before running away to Dragontown in Fillydelphia after Sunset leaves through the portal.
Trahzo

Alright, now we need Sunny & Twi to introduce their assistants with them having that Rainbow Dash duck face while watching their adorable 1st impressions of each other.