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JosieTranello
Perfect Pony Plot Provider - Uploader of 10+ images with 350 upvotes or more (Questionable/Explicit)
Twinkling Balloon - Took part in the 2021 community collab.
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends.
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Friendship, Art, and Magic (2017) - Celebrated Derpibooru's five year anniversary with friends.
Artist -
The End wasn't The End - Found a new home after the great exodus of 2012

It's A Trap!
Sassy Service.
 
She just LOOKS the sassy type. And anyone who has been a receptionist should know why one would become sassy with such a job.
Stotter
Wallet After Summer Sale -

That manestyle looks familiar somehow, like I’ve seen a cartoon redhead with it before. Even it was just a background character or a temporary hairstyle for a more important one, I want to know.
Masem
Elements of Harmony - Had an OC in the 2022 Community Collab
Twinkling Balloon - Took part in the 2021 community collab.
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
Fine Arts - Two hundred uploads with a score of over a hundred (Safe/Suggestive)
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Helpful Owl - Drew someone's OC for the 2018 Community Collab
A Really Hyper Artist - 500+ images under their artist tag
A Really Classy Artist - 250+ images under their artist tag
An Artist Who Rocks - 100+ images under their artist tag

@chris the lovable jerk  
One of the things in this season that I appreciate specifically is that they have gone out of their way to try to make one-off or BG character hair styles rather unique and/or memorable, this is no exemption.