Certificate for Exchange 2007 on SBS 2008

Hi All,

I'm going to be migrating emails from Exchange 2007 (SBS 2008) to M365. The certificate is expired and needs to be replaced. Going to need a SAN SSL Certificate installed on the exchange server so we can migrate to M365. Not worried about having to renew the certificate after a months use.

I've read guides using win-acme, but the requirements would mean updating .net etc. and I'm not sure this server would cope with that.

What's the best and safest way to apply a LetsEncrypt SAN cert on Exchange 2007 (SBS 2008)?


I have no clue what the best and/or safest way is for Windows systems, but there are other Windows based ACME clients out there:

certbot is nowadays also available on Windows, a CLI only Python application.

Also, because it's just once and thus don't require any automation, you might even consider a webbased client such as Get HTTPS for free!.


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