Certbot renew --dry-run failed to renew certificate on windows/IIS

I have installed certbot on windows and IIS server. Installation went to good. When try to dry run for autorenew I am getting below errors.

how to solve this issue and set renew for the future?

Welcome @itsmesri

While it is possible to use Certbot with IIS it is not easy. The reason for this error is your system is now configured differently than when you got your original cert.

Your best solution is to switch to using an ACME Client that is designed for Windows. A popular choice is Certify The Web which is a friendly gui. See:


Looks like you've used the --standalone authenticator while IIS wasn't running. And now it's running apparently, thus competing with the --standalone authenticator.

Possible solutions are:

  • use a different authenticator (although I do not have experience with Windows :face_vomiting: so I can't help you with that)
  • temporarily stop IIS while renewing
  • use a different client with more IIS integration as suggested by Mike

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