Every image compressor only goes one way. That's why your form upload keeps failing.

There's a bug in an entire category of software, and once you see it you can't unsee it.

Government and university application portals ask for a photo like this:

*Photograph: 200×230 pixels, between 20 KB and 50 KB, JPEG only.

*

Read that carefully. It's not a maximum. It's a range.