Hey Barry,
Just a heads up, for the Let's Encrypt issue, it’s worth checking if the server can directly access the domains it’s trying to generate certificates for. If those URLs aren’t reachable from the server (due to DNS, firewall, or proxy issues), the renewal will fail.
On the IIS binding error that Pusparaj Raut ran into, it looks like SmarterMail is handling the cert import, but this error can also pop up if the Centralized Certificate Store is enabled while trying to assign a dedicated certificate manually. That combo tends to cause conflicts in IIS.
If the problem sticks around or you run into anything else, I’d suggest opening a ticket with the support team so they can dig in further.
Kind regards,
Zach Sylvester
Software Developer
SmarterTools Inc.
www.smartertools.com