Error: Validation of the required challenges did not complete successfully

Greetings All,

We’ve had Certify The Web installed and running on our Windows SBS 2011 server since last year, and it’s been working great. Now suddenly we’re getting the following error when it tries to auto renew our SSL certificate:

Validation of the required challenges did not complete successfully

Does anyone have an idea as to what might have happened? We tried to uninstall/reinstall the program but that didn’t work.

Since this forum doesn’t seem to allow the uploading of files other than images, here is a link to a log file of our most current attempt, in case anyone can shed some light on this issue:



If you read through the log you’ll see that toward the end (2019-11-19 20:58:15.256 onwards) your certificate order is working for the and but not for ‘’, so check that all these domains resolve to the same server for both IPV4 and IPV6 and that port 80 is open on the firewall to allow the Let’s Encrypt validation test request through. You will also see that the certifytheweb api also proxies an http config check before it runs the validation (optional under Authorization > Http-01 > Perform challege response config checks) and these tests are failing, which means you probably have firewall rules that prevent these test requests getting through via http (perhaps you filter on remote IP).

As an aside, please don’t store your post-request powershell scripts under C:\Program Files\CertifyTheWeb\scripts\common\ as this directory will be deleted when the app next updates itself and you will lose your scripts.


Yes we I did actually read through the log. It just seemed odd that everything was working fine for months, and then suddenly began failing. My guess is the “perform challenge response config checks” box was accidentally checked because that should be disabled for us. With that said, now everything is working as it should.

Thank you.


Great, glad it’s working ok now.