Deavon, can you send out a copy of your IIS log as you ran the rpcping ? (sidm@microsoft.com). What version of rpcping are you using ? What is the configuration of your mailbox servers. They aren't behind a loadbalancer are they ? What's services.giodivinecom .. a VIP ?
Nikon, the fix for the IPv6 issue will be available in RU4. The fix for the kernel mode issue will be available shortly thereafter.
Jamie, as you and pufferdude point out, the real issue is the Outlook delay to fallback from TCP to HTTPS. A simple TCP check to a server is insufficient since the protocol could be blocked at multiple levels. So, full connecitivity must be established, and if that fails using TCP fallback to HTTP. I suspect the logon for each connection imposes some overheads causing the fallback to be slower than a quick ping.
Plazaai, what auth method are you using ?