Outlook requires login to Sharepoint Calendar each time.

I have a Business class account. I'm attempting ot use a Share Point Calendar and sync it to outlook for members of a team. We are all using Outlook 2010 that is connected to a Comcast Exchange server.

After much searching I learn that the only way to find the button that will sync a SP calendar to outlook is to use IE and add Comcast.net to the compatibility list.

Now that that has been done, I can see the calendar. The problem I have is that each time I start Outlook, I'm asked for login credentuals. Yes, I have checked the Remember My Credentials button....

When I enter the password and click ok, it seems to work. Then the very next time I start Outlook, I get the same prompt. After providing login credentials Outlook kicks out a connection error shown below:

Task 'SharePoint' reported error (0x00040102) : 'Outlook cannot connect to the SharePoint List (Lake County Indiana Electrician's JATC - Instructor Schedule). The server may not be reachable from your location. Contact the SharePoint site administrator for more information.  HTTP 0. An error occurred connecting to http://w14spw-ch2-d1/sites/697JATC. A connection to https://www.w14d.comcast.net/sites/697JATC, an alternate Web address for this SharePoint site, will be attempted.'

Any ideas?