Update certificate with certbot to add subdomain

Question

I have a domain with a LetsEncrypt certificate installed and apache conf setup to forward www to non-www and non-ssl to ssl. Everything was working great until I decided to add a subdomain and tried to generate a new certificate to cover both.

Now I get the following output when I run certbot:

root@arthas:~# certbot
Saving debug log to /var/log/letsencrypt/letsencrypt.log
Plugins selected: Authenticator apache, Installer apache

Which names would you like to activate HTTPS for?
- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
1: domain.com
2: playground.domain.com
3: www.playground.domain.com
4: www.domain.com
- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
Select the appropriate numbers separated by commas and/or spaces, or leave input
blank to select all options shown (Enter 'c' to cancel): 1,2,3,4

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

It contains these names: domain.com, www.domain.com

You requested these names for the new certificate: domain.com,
playground.domain.com, www.playground.domain.com, www.domain.com.

Do you want to expand and replace this existing certificate with the new
certificate?
- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
(E)xpand/(C)ancel: e
Renewing an existing certificate
Performing the following challenges:
http-01 challenge for domain.com
http-01 challenge for playground.domain.com
http-01 challenge for www.domain.com
http-01 challenge for www.playground.domain.com
Waiting for verification...
Cleaning up challenges
Deploying Certificate to VirtualHost /etc/apache2/sites-enabled/000-default-le-ssl.conf
Created an SSL vhost at /etc/apache2/sites-enabled/000-default-le-ssl.conf
Deploying Certificate to VirtualHost /etc/apache2/sites-enabled/000-default-le-ssl.conf
Deploying Certificate to VirtualHost /etc/apache2/sites-enabled/000-default-le-ssl.conf
An unexpected error occurred:
ValueError: Unable to set value to path!
Please see the logfiles in /var/log/letsencrypt for more details.

IMPORTANT NOTES:
 - Unable to install the certificate
 - Congratulations! Your certificate and chain have been saved at /etc/letsencrypt/live/domain.com/fullchain.pem
   Your key file has been saved at: /etc/letsencrypt/live/domain.com/privkey.pem
   Your cert will expire on 2019-07-19.
   To obtain a new or tweaked version of this certificate in the future, simply run certbot again with the "certonly" option.
   To non-interactively renew *all* of your certificates, run "certbot renew"
 - Some rewrite rules copied from /etc/apache2/sites-enabled/000-default.conf were disabled in the vhost for your HTTPS site located at /etc/apache2/sites-enabled/000-default-le-ssl.conf because they have the potential to create redirection loops.

Also, I've copied in the contents of my 000-default.conf file below:

# Added to mitigate CVE-2017-8295 vulnerability
UseCanonicalName On

<VirtualHost *:80>
        ServerAdmin webmaster@localhost

        ServerName domain.com
        ServerAlias www.domain.com

        DocumentRoot /var/www/html

        <Directory /var/www/html/>
            Options FollowSymLinks
            AllowOverride All
            Require all granted
        </Directory>

        ErrorLog ${APACHE_LOG_DIR}/error.log
        CustomLog ${APACHE_LOG_DIR}/access.log combined
        RewriteEngine on
        RewriteCond %{SERVER_NAME} =www.domain.com [OR]
        RewriteCond %{SERVER_NAME} =domain.com [OR]
        RewriteRule ^ https://%{SERVER_NAME}%{REQUEST_URI} [END,NE,R=permanent]
</VirtualHost>
<VirtualHost *:80>
        ServerAdmin webmaster@localhost

        ServerName playground.domain.com
        ServerAlias www.playground.domain.com

        DocumentRoot /var/www/html/playground

        <Directory /var/www/html/playground>
            Options FollowSymLinks
            AllowOverride All
            Require all granted
        </Directory>

        ErrorLog ${APACHE_LOG_DIR}/error.log
        CustomLog ${APACHE_LOG_DIR}/access.log combined
        RewriteEngine on
        RewriteCond %{SERVER_NAME} =www.playground.domain.com [OR]
        RewriteCond %{SERVER_NAME} =playground.domain.com [OR]
        RewriteRule ^ https://%{SERVER_NAME}%{REQUEST_URI} [END,NE,R=permanent]
</VirtualHost>

Answer 1

Same error message for me when trying to install certificates for multiple domains in one go. If you have all VirtualHost in the same configuration file and don't want to separate them, try installing certificate for the domains separately.

Example:

When you need to install certificates for the following domains

1. domain01.com
2. www.domain01.com
3. domain02.com
4. www.domain02.com

At the step

Select the appropriate numbers separated by commas and/or spaces, or leave input blank to select all options shown (Enter 'c' to cancel): 1,2,3,4

enter 1, 2 instead of 1,2,3,4, then repeat to install for 3, 4