I've written some instructions so people will stop complaining about the flags glitch on /sudo/. Basically the workaround to the problem is to wait at least 5 minutes each time when modifying anything on the flag page. These instructions will inform new board owners who come across this problem.
Please replace:
>Flags are likely heavily cached by your browser and the website. Please give them time to update if you change one!
with:
>The flags are currently heavily cached by our servers until we figure out a better solution. You may have to wait 5-10 minutes each time when adding or modifying a flag, or you will experience unexpected behavior where uploading a flag replaces the previous recently uploaded flag. Broken flags can be fixed by modifying their images.
I was going to post this on /sudo/ but it seems to be spammed by bots, so please forward this to Ron so he can take a look when he has time.