System details:
Server: Apache, Ubuntu 16.02
Client: Windows 10, Chrome
My apache config file looks as follows:
<VirtualHost *:80>
       ServerName mycoolsiteA.mydomain.com
       ServerAlias mycoolsiteB.mydomain.com
       Alias /static /var/www/python/mysite/static
       Alias /templates /var/www/python/mysite/templates
       WSGIDaemonProcess my_app user=www-data group=www-data threads=5
       WSGIScriptAlias / /var/www/python/mysite/start.py
       WSGIScriptReloading On
       <Directory /var/www/python/mysite>
               WSGIProcessGroup my_app
               WSGIApplicationGroup %{GLOBAL}
               order deny,allow
               Allow from all
       </Directory>
</VirtualHost>
When I load the css in a browser it is showing the following. However, this is quite random. It "sometimes" works, and sometimes does not.
My example url is this: https://mycoolsiteA.mydomain.com/static/css/bs/bootstrap.min.css
We do have a Firewall appliance which auto-redirects http to https, but I'm loading the css directly with https.
And the result looks like this:

Yet, if I refresh several times, or add a r=number on the end, it will clear the cache and load. But, it will do it again randomly until I clear the cache again.
Here it is loaded and working:
Any thoughts, direction on where to look to fix this?

 
    