Environment: Exchange 2007 SP1. Outlook 2007.I have a strange issue that I can not find a resolution on. Under normal circumstances, Outlook 2007 displays user and conference room schedules when using the exchange calendar feature. However, when the user connects over the web using Outlook Anywhere, the schedule for those objects is grayed out with slashes and "no free/busy informationn could be retrieved" is listed when hovered over.I've done all the sugested DNS work both local and on our Internet DNS servers, and also URL and SSL certificate changes through EMS, but this strange little behavior keeps happening, so I think I missed something, and may have narrowed it down to a Exchange config issue. The reason I think this is that when I vpn into the office, the IP address for the exchange server is resolving to a private IP address, however the outlook schedule DOES NOT behave like the machine is internal, instead the objects listed above's schedules continue to be grayed out.One last strange behavior. I had to setup a cname for "autodiscover.domain.com" to point to my OWA URL over https. There is one issue that arises when I do an autodiscover test through outlook, and that is that the certificate name mismatch warning, which I click through. After that, the test succeeds with the correct non-autodiscover A records for my OWA server, but I'm wondering if that the default autodiscover.domain.com search is revealing that Outlook can't deal with a certificate mismatch, as this method Outlook uses when the Exchange server is local is slightly different.

Hell Medfordjared, When you run Test e-mail autoconfiguration from an external client, do you receive all the web services used by the external client? When you use Autodiscover in a computer that belongs to the domain, it uses SCP not DNS configuration. The best way is to follow the best practices and assign an autodiscover.company.com to your deployment. If you have only Outlook 2007 SP1 outside, you can use the same cert that you already have (I'm assuming that you are using a valid one) and just add the SRV records in your external DNS. Check this out: http://technet.microsoft.com/en-us/library/bb332063.aspx