SSL for SBS2011 - URGENT

[Charlton]

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)

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.

Cheers

Charlton

[JuergenAuer]

Hi @Charlton

@Charlton

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

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.

[Charlton]

Hi Jurgen

I think I’m supposed to secure ‘mail.domainname.com.au’ which is on-premise.

Looking into that now.

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

[JuergenAuer]

@Charlton

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

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

First, read the basics:

How It Works - Let's Encrypt

Then select a client.

ACME Client Implementations - Let's Encrypt

The client creates the CSR on the fly.

[schoen]

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

[Charlton]

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.