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catbox.moe says that "The operation could not be completed due to a lack of memory", which is strange, because larger files but with image/video/plaintext extensions work fine...?
Why isn't it letting me upload a .TTF?
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No idea...
UPDATE: Refreshing fixed it.
By "Neospring assumes it's an image for some reason" do you mean it gets proxied, but replaced by a placeholder image? That to me sounds like nekoweb is throwing a captcha at Neospring.
Try reuploading the ttf file to catbox.moe and using that URL