SSL for SBS2011 - URGENT

Hi guys

I’m a clueless newbie at this so please be kind. (Also, I’m not sure I put this request in the correct category) :slight_smile:

I’m about to migrate from Exchange on SBS2011 to exchange365. I need to add an SSL cert to the on-premise SBS2011 server that is hosting the emails. The website is hosted by a commercial hosting company.

My question is when issuing an SSL, do I point the address to the domain or to the on-premise IP address?

I have a BAAAAD feeling I’m going to stuff this up ROYALLY but I’ll give it a shot before panicking.



Hi @Charlton

a certificate has one ore more domain names. It's possible to create a certificate with an ip address - but that's rare. Letsencrypt doesn't support that.

So use the domain name.

Hi Jurgen

I think I’m supposed to secure ‘’ which is on-premise.

Looking into that now. :slight_smile:

I have the CSR. ALL I have to do now is work out how to generate the SSL. :roll_eyes:

If you want to use Letsencrypt directly, you don't need to create a CSR manual.

First, read the basics:

Then select a client.

The client creates the CSR on the fly.

(Normally, you’ll run the Let’s Encrypt client on the server itself.)

I started using CertBot only to find that I couldn’t use anything with Windows SBS2011 so I ended using CertifyTheWeb and it APPEARS to have worked (although I still couldn’t do the automated Cutover Migration to Exchange 365 and I have no idea what caused that glitch).

Thank you for all your help guys.

Much appreciated. :slight_smile:

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