I have just installed a SBS2011.
I also have applied a valid Thawte 123SSL certificate and have confirmed that this is working.
I have 10 users which logs in to the domain from their laptops and access their email with locally installed Outlook 2010.
I use the autodiscover function in Outlook to set up their mail accounts.
I also have 5 clients using laptops outside the LAN.
These 5 pc's does not log onto the domain nor is configured for this.
Outlook is therefore configured manually with exactly same settings as the other Outlook clients.
This includes settings under "more settings" "network" and "HTTP".
These clients was configured and tested inside the LAN and Outlook worked perfectly.
However when the clients goes outside LAN Outlook fails to connect!