Configuring SSL with LetsEncrypt

So after quite a bit of tinkering I am now able to configure a site on an Ubuntu 18.04 LTS VPS.

Where I’m struggling however is how to enable SSL using a LetsEncrypt certificate. I used the following command to update the previously installed site:

ee site update --ssl=le

The dialog requested my ‘email id’, to which I responded with the email address under which my domain ( is registered. I then got a message that the “Challenge failed”.

Am I correct in entering the email address registered to the domain name when asked for my mail id? Or should I provide some other response?

Hoping someone can help me sort this out (Note that I am using Cloudflare - do I need to change this while configuring SSL?)

Just to clarify, you do have a live domain ( and installed your site under it using EE, AND able to get to your non SSL site ( in your browser?

To enable SSL using Let’s Encrypt I would suggest you to go through the reference tutorial Let’s Encrypt WordPress SSL. You can also redirect website to https adding the following code in .htaccess file

RewriteEngine On
RewriteCond %{http:X-Forwarded-Proto} !HTTPS
RewriteRule ^(.*)$ https://%{HTTP_HOST}/$1 [R=301,L] 
# BEGIN WordPress
<IfModule mod_rewrite.c>
RewriteEngine On
RewriteBase /
RewriteRule ^index\.php$ - [L]
RewriteCond %{REQUEST_FILENAME} !-f
RewriteCond %{REQUEST_FILENAME} !-d
RewriteRule . /index.php [L]
# END WordPress

Typically, when it fails a challenge with no wildcard option set it means your DNS provider isn’t pointing to the correct server. What is your URL? Like @ninjaroll said above, you should be able to get to your website via the URL you want to set up SSL on. I would warn that following @amandajames instructions probably isn’t the best idea. I am not saying they wouldn’t work but the entire point of EE is to have everything configured by scripts that can be maintained and edited via EE and just adjusting your .htaccess file could cause issues, especially since most container settings get reset after system restarts or docker restarts.