Weird thing, I'm using Sharepoint WSS 3.0 and Outlook 2007 with one of my Sharepoint task lists connected to Outlook. Connecting it the first time works perfectly fine and I can access it. If I close Outlook however and re-open it, I get a 302 error like Outlook cannot authenticate to Sharepoint. I have IIS redirecting port 80 requests to 443 to prevent unsecure use of Sharepoint. What could be causing Outlook not to reauthenticate for the Sharepoint Task List when opening it? How can I fix this?