I'm having a similar issue as the user here. I'm running an Ubuntu 14.04.4 droplet and using Apache2 for the webserver.

My current redirect setup goes like this:

• http://example.com --> https://example.com works
• http://doesnt-exist.example.com --> https://example.com works
• https://example.com/doesnt-exist --> https://example.com/404 works
• http://example.com/doesnt-exist --> example.comdoesnt-exist ERROR

The last one is where the problem is. For some reason, my permanent HTTP to HTTPS redirect fails if a subdirectory or file is also part of the URL. On Chrome, I get redirected to a ERR_CONNECTION_REFUSED page for example.comdoesnt-exist (obviously not a real domain) over HTTPS. For that last case, I want to have it arrive at my catch-all 404 page over HTTPS.

Here's my 000-default.conf file (I'm not using an .htaccess file):

<VirtualHost *:80>
    ServerName example.com
    Redirect permanent / https://example.com
</VirtualHost>

<VirtualHost *:443>
    ServerName example.com

    ServerAdmin webmaster@localhost
    DocumentRoot /var/www/html

    SSLEngine on
    SSLCertificateFile <location here>
    SSLCertificateKeyFile <location here>

    SSLCACertificateFile <location here>

    ErrorLog ${APACHE_LOG_DIR}/error.log
    CustomLog ${APACHE_LOG_DIR}/access.log combined

    ErrorDocument 404 /404.html
    ErrorDocument 400 /400.html
</VirtualHost>

<Directory /var/www/>
    Options Indexes FollowSymLinks MultiViews
    AllowOverride All
    Order allow,deny
    allow from all
</Directory>

I'm a newbie at this so there's probably an embarassing mistake in here

I greatly appreciate any help!