I have configured our Exchange 2007 SP3 server with Outlook Anywhere, so that staff working externally can connect to the Exchange server over port 443 using Outlook 2007. This was done so that staff didn't have to use Outlook Web Access and it allowed a simplified firewall configuration without the staff members having to VPN into the office network first (which was how we used to do it)
Mail flow seems to work fine - that is a *preconfigured* account can receive mail no problems. When I say *preconfigured* that is actually part of the problem
It is not possible for a clean install of Outlook externally to connect to the mail server to be configured. When it gets to the "Check Name" part of the process, it just times out and then gives an error about the name not being able to be resolved and that Outlook needs to be online to complete the process.
If I VPN into the office network first, then I can setup the account fine.
The mail server only has port 443 open on it, and I know that the Outlook Anywhere is configured correctly because we're using it for our internal mail as well (as it simplifies the firewall setup on the mail server). So, regardless of where Outlook is external or internal, it is speaking to the mail server on port 443 (the difference being with internal clients is they can access the domain controller, and external clients cannot)
I know that the external traffic is being correctly routed to the mail server, since OWA works fine.
It seems to me that there need to be additional ports open to allow external clients to authenticate themselves, but that goes against my belief that Outlook Anywhere was supposed to work completely over just port 443
Any advice would be greatly appreciated.