We have Outlook Web Access setup on the Exchange 2010 server and it has been running for over a year. We have an ssl certificate tied to it. Most external users, or at home users, then simply use OWA. A user requested to use Outlook Anywhere. I enabled Outlook Anywhere on the Exchange server and then made the Outlook client changes on a remote PC to test. In the docs, it says to use "Basic Authentication" if the computer attaching is not a member of the domain - this would be true. The firewall is a Cisco ASA 5510. Is there any reason to believe setting up Outlook Anywhere is any less secure than the OWA configuration?