I'm trying to configure my website to redirect all traffic to the www subdomain, and redirect all http requests to https requests. I know it's not a problem with by DNS records (which include an A record for www and cloud) because my configuration worked perfectly until about a week ago when I reinstalled everything. The problem experienced is that it behaves very funkily.
(I've replaced my domain with "example.com" to sanitize the post.)
What doesn't work:
http://example.com - redirects to https://www.example.com,
but yields SSL_PROTOCOL_ERROR
http://cloud.example.com - redirects to https://www.example.com/myfiles/,
but yields SSL_PROTOCOL_ERROR
https://example.com - no redirect to www, and yields SSL_PROTOCOL_ERROR
https://www.example.com - yields SSL_PROTOCOL_ERROR
https://cloud.example.com - no redirect to www, and yields SSL_PROTOCOL_ERROR
What does work:
http://www.example.com - works like a dream
All of my Apache Configuration Steps (from a clean install):
sudo echo -e "\\ndeb http://ftp.debian.org/debian jessie-backports main" >> /etc/apt/sources.list
sudo apt-get update && sudo apt-get -y upgrade
# Because you'll want the latest certbot...
sudo apt-get -y install python-certbot-apache -t jessie-backports
sudo apt-get -y install apache2 php5 libapache2-mod-php5 php5-mcrypt php5-mysql php5-cli
sudo a2enmod rewrite
Put the following (as root) at the end of /etc/apache2/apache2.conf
ServerName example.com
<VirtualHost *:80>
ServerName example.com
Redirect permanent / https://www.example.com/
</VirtualHost>
<Directory /var/www/(.*)>
RewriteEngine On
RewriteCond %{HTTPS} off
RewriteRule (.*) https://%{HTTP_HOST}%{REQUEST_URI}
</Directory>
Creating the VirtualHosts and Certificates
sudo tee /etc/apache2/sites-available/www.conf << "EOP"
<VirtualHost *:80>
ServerName www.example.com
Redirect / https://www.example.com/
</VirtualHost>
<VirtualHost *:443>
DocumentRoot /var/www/html/
ServerName www.example.com
</VirtualHost>
EOP
sudo a2ensite www
sudo service apache2 restart
sudo certbot --apache --domain www.example.com
#I apply this to /etc/apache2/sites/enabled/default-ssl.conf
sudo mkdir -p /var/www/html/myfiles/
sudo tee /etc/apache2/sites-available/cloud.conf << "EOP"
<VirtualHost *:80>
ServerName cloud.example.com
Redirect / https://www.example.com/myfiles/
</VirtualHost>
<VirtualHost *:443>
ServerName cloud.example.com
Redirect / https://www.example.com/myfiles/
</VirtualHost>
EOP
sudo a2ensite cloud
sudo service apache2 restart
sudo apache2ctl configtest #which reports everything's ok
More Information about Server:
The server is a clean install of Debian 8.6 (amd64), and the Apache version number is 2.4, so stability of the software isn't the issue.
My SSL Problem
A cat /var/log/apache2/error.log throws me the following:
[ssl:warn] [pid 11737] AH01909: www.example.com:443:0 server certificate does NOT include an ID which matches the server name
