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and they will still optimize on upload
If you're making them undergo lossy compression
anyway (which seems to be the case if I interpret you correctly) there's no need.
In practice if I needed to upload a PNG file (after doing that directly became impossible) I used whatever random online converter I googled up that day (that had a lossless setting) to convert it to WEBP, then uploaded that. I suspect that most WEBP files I uploaded before this year were those; it's a pretty rare format otherwise.
I'm not sure if those would now be lossily-compressed
too even if they're under 300 kilobytes. If yes... I guess Imgur or whoever are my friend now.
2017 sounds plausible. I guess it doesn't feel
that long ago...
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All that's changed is I added webp a few years ago to the end.
The error message I got must have been older than that, because it only listed JPG, JPEG, and GIF.