Let's Encrypt Not Renewing

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My domain is: advanceraven.com

I ran this command: sudo certbot renew --dry-run

It produced this output:

Simulating renewal of an existing certificate for advanceraven.com and 4 more domains

Certbot failed to authenticate some domains (authenticator: apache). The Certificate Authority reported these problems:
  Domain: advanceraven.com
  Type:   connection
  Detail: During secondary validation: 71.164.95.180: Fetching http://advanceraven.com/.well-known/acme-challenge/LkTzALHRz0JQfcDK1JQ9-5ppCnoflAjGqAn0LFle3gs: Timeout during connect (likely firewall problem)

  Domain: dev.advanceraven.com
  Type:   connection
  Detail: During secondary validation: 71.164.95.180: Fetching http://dev.advanceraven.com/.well-known/acme-challenge/XlhTUrliAzPSTq_DzpCXLkfaJOVWsUhpHiPWM6md920: Timeout during connect (likely firewall problem)

  Domain: gov.advanceraven.com
  Type:   connection
  Detail: During secondary validation: 71.164.95.180: Fetching http://gov.advanceraven.com/.well-known/acme-challenge/nm1B4BKHwyEqedPxQp0fKk-rzje7uwOoY0URVjS7SLo: Timeout during connect (likely firewall problem)

  Domain: portal.advanceraven.com
  Type:   connection
  Detail: During secondary validation: 71.164.95.180: Fetching http://portal.advanceraven.com/.well-known/acme-challenge/3GQqQ_xMV8sad33M3DuWMCXjVfRGRQl349Oof8tKZVw: Timeout during connect (likely firewall problem)

  Domain: www.advanceraven.com
  Type:   connection
  Detail: During secondary validation: 71.164.95.180: Fetching http://www.advanceraven.com/.well-known/acme-challenge/ALqB4ycuofk-iQzLsoD--xL8waOHyvVL80TpAT0YECo: Timeout during connect (likely firewall problem)

Hint: The Certificate Authority failed to verify the temporary Apache configuration changes made by Certbot. Ensure that the listed domains point to this Apache server and that it is accessible from the internet.

Failed to renew certificate advanceraven.com with error: Some challenges have failed.

My web server is (include version): Apache/2.4.52 (Ubuntu)

The operating system my web server runs on is (include version): Ubuntu 22.04.4 LTS

My hosting provider, if applicable, is: Self Hosted

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

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

The version of my client is (e.g. output of certbot --version or certbot-auto --version if you're using Certbot): 2.10.0

I have already looked through various other topics to troubleshoot and am stuck

Port 80 and 443 are indeed open. This has been verified using nmap and telnet.

I have reviewed the firewall rules and nothing is blocking 443 or 80

I have verified the Apache virtual host directives to ensure they are configured properly, all checks out (note this was all working nicely for quite some time until about 2 weeks ago)

The web server is listening on 80 and 443, this was verified using netstat -tunlp | grep 80 & netstat -tunlp | grep 443

I have been using the --apache flag consistently, and just ran several webroot tests without success

I have on another server a manual Lets Encrypt setup that uses DNS ACME Challenge and has zero issue. Am using the --apache flag as this particular server runs about 40 domains, all of which have renewed without issue for years.

I have even utilized the LetsDebug utility to troubleshoot and am running low on ideas.....

I did happen to notice a New order message during a renewal attempt a day ago, so not sure if a limit was hit or if I truly am missing something.....

Any ideas?

The "During secondary validation" part in combination with the timeout error suggests you're geoblocking access to your server.

Let's Encrypt uses multiple validation from all around the world and recently added some other remote validation points.

Please note that Let's Encrypt does not officially shares lists of IP addresses and/or locations from which these remote validations are occuring and these locations could change at any moment.

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Welll.....that was amazing. We did have geolocation blocks in place because we run some government services, disabling that on the firewall allowed ALL of our domains to renew successfully. Very much appreciate your wisdom.

4 Likes