It seems the css for a sub can only be changed once, further changes don't seem to take effect.
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Right now the custom CSS is being parsed and checked if it's valid, with some custom validation rules I added like no URLs, then saved. The problem is that ALL user-uploaded files are being cached, for hours it seems. Even things like avatars. So I need to fix this. I'm GUESSING laravel octane is causing the issue but I can't find anyone else with this issue.
It seems that it is possible to programatically clear/update the cache, you could do a task that is run every 5 minutes to update the cache.
Programatically clear the cache: https://tinkerwell.app/blog/laravel-caches-and-all-ways-to-clear-them
I use these caches as well but they wouldn't affect files.