My suspicions were correct.  Setting up a domain in the form of pydio.server.com and using the below config will work out the box with a fresh pydio install.  So that's going to be my advice.  It does tend to work better with apps like this and nextcloud.   <VirtualHost *:80> ServerName pydio.server.com ServerAlias pydio.server.com DocumentRoot /config/www/ Redirect permanent / https://pydio.server.com/ </VirtualHost> <VirtualHost *:443> ServerName pydio.server.com Serve