How to get a certificate for Windows SBS 2011?

I have a client with an older Microsoft Small Business Server 2011.
(SBS 2011)

There is this fancy (and very picky) control panel that you are VERY STRONGLY advised to use to manage this server since the whole thing is stitched together using hundreds of scripts to automatically configure the whole stack.
Exchange 2011
Outlook Web Access
RDP, etc.

Is it possible to get a cert from Lets Encrypt that we can use via this “approved console”?

I dont want to break anything, but we seriously need to add a certificate for SSL, TLS and the other aspects of this server.

It’s insecure now.


Unfortunately the best response I can give you is a list of Let’s Encrypt Windows Clients.

Reading back your description you should see why this is the best I can do :wink:

They have different levels of automation that may or may not do what you require

There are also several discussions on this forum on how to configured various aspects of Windows (IIS, SQL,RDP)


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