Creating Cert for Icecast server - Challenge Failed for domain

To add in the following information.
I run Windows IIS Web Server(s) for all my domains.
I have created a sub-domain called "Stream" for using Icecast.
I am not certain if this is causing the issue or not. It can only access Port 80 and 443 on the Windows server, and the only port accessible for the Icecast server is port 5000.

I honestly don't know how to make this work in any way. I cannot point port 80 or 443 to the Linux server without dropping access to the LIVE Windows Web Server(s).

My domain

I ran this command:
(I installed everything which was needed to do the cert on Linux
With instructions from the following website.
icecast https ssl setup lets-encrypt)
wget -qO - | sudo apt-key add -
apt-get update
apt-get install certbot
sudo certbot certonly --webroot-path="/etc/icecast2/web/" -d ''

It produced this output:

Challenge failed for domain
http-01 challenge for
Cleaning up challenges
Some challenges have failed.

 - The following errors were reported by the server:

   Type:   unauthorized
   Detail: Invalid response from
   []: "<!DOCTYPE html PUBLIC \"-//W3C//DTD XHTML 1.0

   To fix these errors, please make sure that your domain name was
   entered correctly and the DNS A/AAAA record(s) for that domain
   contain(s) the right IP address.

My web server is (include version):

The operating system my web server runs on is (include version):
Ubuntu 20.04.2 LTS

My hosting provider, if applicable, is:
Self-owned provider

I can login to a root shell on my machine (yes or no, or I don't know):

I'm using a control panel to manage my site (no, or provide the name and version of the control panel): No.

The version of my client is (e.g. output of certbot --version or certbot-auto --version if you're using Certbot):

Any information or assistance on how to set this up to run would be great.
Thank you.


What version of IIS are you running?


This topic was automatically closed 30 days after the last reply. New replies are no longer allowed.