Can not renew SSL ACME IIS10 Simple Windows

My domain is:

My web server is (include version): Windows server 2019.

[INFO] A simple Windows ACMEv2 client (WACS)
[INFO] Software version (RELEASE)
[INFO] IIS version 10.

I have 2 websites on my IIS 10 as specified above using ACME let’s encrypt, 2 months and a half no issue ever here. I create the task scheduler so this will auto-renew by himself. Now I am in the last 20 days I checked why was not renewed and I run into this issue.

Try to renew using the power shell interface on ‘‘Renew Specific’’, try to create a new one using create a new certificate but it same issue. It’s just hanging there around 5 minutes and receiving this error.
[EROR] (TaskCanceledException): A task was canceled.

I have port 443 and 80 opened, I restart IIS and is the same issue. I do not understand why is this issue as nothing has been changed since 2 months ago where there was no issue.

Any suggestions I will appreciate.

Hi @Liviu.Busuioc

checking your domain - that’s curious -

The online check sees the expected result checking http + /.well-known/acme-challenge/random-filename -> http status 404 - Not Found.

But checking it with a small offline tool:

D:\temp>download -h
Status: 500 InternalServerError

Looks like your configuration is buggy. Why there are different answers?

Both answers have

Server: Microsoft-IIS/10.0
X-AspNet-Version: 4.0.30319
X-Powered-By: ASP.NET

Hi Juergen,

Thank you for your response.

So where will be the bug, do I need to check the web config file and make some changes there?

I do not want to take down the actual website.

This has been fixed.

The binding was pointing to the internal IP address of the server , changing this to * (so it picks up DNS record), rebooted the instance and done it again.

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