SSL certificate on Windows Server 2012R2, IIS8.5 (DMZ Server)

We have a server in our DMZ, which already had an SSL certificate, but it has expired. Now we would like to start with this server to switch to Let’s Encrypt.
I also successfully imported the certificate via win-acme. Unfortunately the site is not accessible from outside (my workstation / smartphone) via https (

I access the URL ( from my workstation and no successful SSL connection can be established. Under the details of this rejection i can find the old certificate (just why?).
However, when I call this url on the server (remote desktop session, a secure connection can be established.

Unfortunately, I have no idea what to look for. I tried a lot today, but found nothing that would even begin to describe my problem.

Does anyone have any ideas or ideas for me?

Hi @phil90

what's your domain name? If your server sends the wrong certificate, the binding isn't updated. But I don't know if win-acme does this automatic.

Remote Desktop uses own certificates. There it's also possible to use self signed certificates.

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