If you are experiencing issues with Outlook Anywhere on your SBS 2008 network, check out this insightful post by the SBS support and product team. The post addresses HTTP to HTTPS redirect issues in the SBS Web Applications App Pool and offers a step-by-step of checking the Worker Processes and removing the HttptoHttpsRedir module from the /RPC virtual directory in IIS.
Thanks SBS team!
http://blogs.technet.com/sbs/archive/2009/01/28/slow-connectivity-for-outlook-anywhere-and-sites-that-use-the-sbs-web-applications-app-pool.aspx