Short answer
Resize to the destination's required dimensions first, then compress only as much as needed to pass the file-size limit.
Resize to the destination's required dimensions first, then compress only as much as needed to pass the file-size limit.
Resize to the destination's required dimensions first, then compress only as much as needed to pass the file-size limit.
Upload limits often care about both pixel dimensions and file size, so compression alone may not be enough.
Photos can usually be resized aggressively for forms while preserving enough visual information.
Screenshots with text need more careful resizing because small text becomes unreadable quickly.