Using Debian 11's Apache to reverse proxy a legacy HTTPS site, with SSL certificate provided by Certbot/Let'sEncrypt

A common requirement when dealing with obsolete combination of OS and applications.

Credits/bibliography

I've been following this site's hints here

https://blog.containerize.com/2021/05/21/how-to-configure-apache-as-a-reverse-proxy-for-ubuntudebian/

Assumptions

  • Your old, not updateable combo of webserver and application has IP address 192.168.105.37
  • It's currently published on the Internet and its public DNS' FQDN is theoldsite.fsmn.xyz
  • Your new server can reach the Internet and is reachable from there on both 80/TCP and 443/TCP
  • You can manage public DNS records

Apache installation and activation of reverse proxy and SSL modules

sudo apt update -y
sudo apt upgrade -y
sudo apt install -y apache2
sudo a2enmod proxy
sudo a2enmod proxy_http
sudo a2enmod proxy_balancer
sudo a2enmod lbmethod_byrequests
sudo a2enmod ssl
sudo systemctl restart apache2

Create initial site config, HTTP->HTTP

You'll have to create a new *.conf file under /etc/apache2/sites-available/

# revproxy.conf
<VirtualHost *:80>
        ServerName newsite.fsmn.xyz
        ServerAdmin webmaster@fsmn.xyz
        ErrorLog ${APACHE_LOG_DIR}/rp-error.log
        CustomLog ${APACHE_LOG_DIR}/rp-access.log combined
        ProxyRequests Off
        <Proxy *>
          Order deny,allow
          Allow from all
        </Proxy>
        ProxyPass / http://theoldsite.fsmn.xyz/
        ProxyPassReverse / http://theoldsite.fsmn.xyz/
        <Location />
          Order allow,deny
          Allow from all
        </Location>
</VirtualHost>

<IfModule mod_ssl.c>
<VirtualHost *:443>
        ServerName newsite.fsmn.xyz
        ServerAdmin webmaster@fsmn.xyz
        ErrorLog ${APACHE_LOG_DIR}/rp-error.log
        CustomLog ${APACHE_LOG_DIR}/rp-access.log combined

        ProxyRequests Off
        SSLProxyEngine On
        <Proxy *>
          Order deny,allow
          Allow from all
        </Proxy>
        ProxyPass / https://theoldsite.fsmn.xyz/
        ProxyPassReverse / https://theoldsite.fsmn.xyz/

        <Location />
          Order allow,deny
          Allow from all
        </Location>
</VirtualHost>
</IfModule>

and add a line to your /etc/hosts so that your reverse proxy host can resolve the old site (possibly via an internal IP address)

192.168.105.37 theoldsite.fsmn.xyz

Enabling the reverse proxy Apache configuration, disable the default Apache

Now you should enable the new 'site' and disable the default one

ferdi@testdebian1:~$ sudo a2dissite 000-default
Site 000-default disabled.
To activate the new configuration, you need to run:
  systemctl reload apache2
ferdi@testdebian1:~$ sudo a2ensite revproxy
Enabling site revproxy.
To activate the new configuration, you need to run:
  systemctl reload apache2
ferdi@testdebian1:~$ sudo systemctl reload apache2

Adding temporary DNS entry to test the HTTPS setup

You have to make sure that newsite.fsmn.xyz resolves to your new server's public IP

Requesting SSL certificate to Let's Encrypt

Just like that! The certificate will be requested and fetched (and a cron job will be created to take care of renewals) and our revproxy.conf will be automagically modified by: - adding RewriteEngine/RewriteCond/RewriteRule to redirect HTTP calls to HTTPS - referencing the new certificate

ferdi@testdebian1:~$ sudo certbot --apache -d newsite.fsmn.xyz
...

Reloading Apache and test

To have our new configuration in place, you have to reload Apache

sudo systemctl reload apache2

Now you can test the redirection via browser, pointing at https://newsite.fsmn.xyz When you're satisfied with your tests, it's time to

Add oldsite.fsmn.xyz as ServerAlias inside your revproxy.conf

Just below the ServerName directive on both VirtualHosts (*:80 and *:443), add the line

ServerAlias oldsite.fsmn.xyz

And reload Apache

sudo systemctl reload apache2

Now it's time to switch oldsite.fsmn.xyz DNS entry to point at the new IP (better doing that off-hours).

Expanding Certbot-provided SSL certificate

Next (quick) action should be to update our SSL certificate to include oldsite.fsmn.xyz.

ferdi@testdebian1:~$ sudo certbot --apache -d newsite.fsmn.xyz -d oldsite.fsmn.xyz
Saving debug log to /var/log/letsencrypt/letsencrypt.log

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You have an existing certificate that contains a portion of the domains you
requested (ref: /etc/letsencrypt/renewal/www.fsmn.xyz.conf)

It contains these names: newsite.fsmn.xyz

You requested these names for the new certificate: newsite.fsmn.xyz, oldsite.fsmn.xyz.

Do you want to expand and replace this existing certificate with the new
certificate?
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(E)xpand/(C)ancel: e
Renewing an existing certificate for newsite.fsmn.xyz and 1 more domain

Successfully received certificate.
Certificate is saved at: /etc/letsencrypt/live/newsite.fsmn.xyz/fullchain.pem
Key is saved at:         /etc/letsencrypt/live/newsite.fsmn.xyz/privkey.pem
This certificate expires on 2023-02-15.
These files will be updated when the certificate renews.
Certbot has set up a scheduled task to automatically renew this certificate in the background.

Deploying certificate
Successfully deployed certificate for newsite.fsmn.xyz to /etc/apache2/sites-enabled/revproxy.conf
Successfully deployed certificate for oldsite.fsmn.xyz to /etc/apache2/sites-enabled/revproxy.conf
Your existing certificate has been successfully renewed, and the new certificate has been installed.

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If you like Certbot, please consider supporting our work by:
 * Donating to ISRG / Let's Encrypt:   https://letsencrypt.org/donate
 * Donating to EFF:                    https://eff.org/donate-le
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and reloading Apache as usual (just in case)

sudo systemctl reload apache2

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