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fair but "it" here is pretty vague. my guess is that, in your case, whatever part of "it" that processes the image handles webp files just fine but for some reason the devs made "it" reject file extensions that don't match ".jpeg", ".png", ".whatever_else" for some reason before the file gets handled further.
Even if a webp is still accepted, I still have that distrust though. The marketing people should have let everyone who works with pics know what they are. I use non-standard software so maybe that's why I'm clueless as to what it actually does. Again, I've got a lot on my plate so it never really comes up as first priority to figure out what it is.
Edit: I thought you were someone else, sorry about that. Still leaving it since it's still valid, lol.
It would be helpful for the discussion if you would tell us what the mystery program is, that is handling images in this strange way and what operating system you are on.
I don't remember, it was a while ago. I'm on windows 10 and I use Affinity for all photo editing. I think it had something to do with a header for a site, that's the distant memory anyway. That's kind of my point, I remember the distrust but not the circumstances. As I told someone else, I'm not trying to bust anyone's balls, feel free to ignore me. I'm just trying to give you the every man perspective. It is just mine and only one perspective.