Receiving SSL Certificate error when running the Exchange Connectivity Analyzer

I take it you have port 443 open on your firewall and that your firewall is port forwarding to your SBS server's internal IP Address?

Visit www.canyouseeme.org and test port 443.  You should see SUCCESS if it is open and forwarded.

If it isn't - check your firewall / router and see if the rule is setup to port forward it and also check to see if you have port 443 grabbed by the router / firewall's Remote Management Port and if it is - change the Remote Management Port to something else such as port 444.

Did it, success on port 443.

I wish it was something simple like that haha!

How did you install the SSL certificate?  Wizard in SBS console or via EMC?

EMC, should I try to install with the SBS console?

As it is SBS, technically the console should be used, but the EMC always works happily for me ;)

Is OWA working happily without any certificate errors?

https://remote.domain.com/owa

Yes OWA works fine, as well as mobile phone sync.  However, for mobile sync, I have to do a manual set up, autodiscover won't find it by the domain name.

This is still outstanding, but I'll close the question as it seems there is no real answer on how to fix this.

But I do appreciate the effort and extremely helpful tips on where to look.

Sorry - dropped the ball on this one.  If your question goes cold, just click on the Request Attention Button.

What names are included in your SSL certificate?

Have you created an Autodiscover A record in your external DNS records pointing to the Public IP address of your server?

The A records are pointing to the server name? Do they need to point to the public ip?   Everywhere I look says different things. I really wish Microsoft had an article with a list of what exactly to do to make this work.  Ugh!!

The sans are servername.domainname.local, webmail.domainname.com, autodiscover.domainname.com, remote.domainname.com

Thank you!