Lets Encrypt certbot failed to authenticate domain with mixed DNS records (AKA do not forget IPv6 records)

Written by Claudio Kuenzler - 0 comments

Published on April 3rd 2025 - Listed in Internet TLS SSL Security Linux

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When using certbot to automatically create certificates from Let's Encrypt, this usually works very well. However the following error can lead to some hair-tearing:

root@debian:~# certbot -n certonly --webroot -w /var/www/letsencrypt -d example.com -d www.example.com
Saving debug log to /var/log/letsencrypt/letsencrypt.log
Requesting a certificate for example.com and www.example.com

Certbot failed to authenticate some domains (authenticator: webroot). The Certificate Authority reported these problems:
  Domain: example.com
  Type:   unauthorized
  Detail: The key authorization file from the server did not match this challenge. Expected "Aq9xXQ2tIjoT3tMr7oE9Yxu4njyxFHMfREqcSmW1EhA.vVjrAf3C5tIJv1Q91oTwu4uKjgxdZwm2lY9YhIOvq2Y" (got "")

  Domain: www.example.com
  Type:   unauthorized
  Detail: The key authorization file from the server did not match this challenge. Expected "1wh7AbwSkEOusY6X9aTHUENQkZs8vgCEAHO69u0yyU8.vVjrAf3C5tIJv1Q91oTwu4uKjgxdZwm2lY9YhIOvq2Y" (got "")

Hint: The Certificate Authority failed to download the temporary challenge files created by Certbot. Ensure that the listed domains serve their content from the provided --webroot-path/-w and that files created there can be downloaded from the internet.

Some challenges have failed.
Ask for help or search for solutions at https://community.letsencrypt.org. See the logfile /var/log/letsencrypt/letsencrypt.log or re-run Certbot with -v for more details.

According to the output, it looks as if the webroot-path was wrong or that certbot did not create the authorization file in the correct path.

But in this situation it was a completely different reason: A mix of IPv4 and IPv6 DNS records.

This particular domain had both IPv4 and IPv6 addresses. Yet only the IPv4 addresses were changed to point to this new Debian server.

Let's Encrypt uses IPv6 by default (at least from what I've seen in the past years). The old IPv6 entries still pointed to the old environment. Hence the traffic actually never landed on our Debian server to retrieve the authorization file via HTTP.

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