Years ago, as far as I can tell. Are you using an older version of the app maybe? I’ve not had Discord outright refuse to send pictures for ~2 years now, for a while it would ask to compress them, now it’ll just automatically compress them (unless it’s so big it can’t of course).

Back in April they also increased the limit to 25MB, so even less stuff should need to get compressed anyway.

A basic photo from my phone is over the file size limit. It’s essentially unusable

For a while this was a problem, but now Discord just auto-compresses photos over 8MB. Obviously this isn’t ideal if you want to actually share the full-size image, but for most use-cases a compressed photo is fine. Almost every other chat app is also compressing your images, it just isn’t telling you it’s doing it outright.

The official term is “cooking up the felonese”