One of my goals with any solution is “simplicity”. Make it easier for users to access the resources they need in a safe and secure manner. Redirecting your general URL for Outlook Web Access/App to the proper secure address makes life for your users much easier. The old method for doing this will no longer work in Windows 2008 R2/Exchange 2010 due to some of the new features (i.e. Remote PowerShell).

There are 2 aspects to configure to enable this.

  1. Redirect traffic to the /owa directory
  2. Allow IIS to listen on port 80 at the top level Reroute http (port 80) to https (port 443)

Here is how to do it in Windows 2008 R2 for Exchange 2010.

Redirect Traffic to the /owa Directory:
Windows 2008 R2 IIS has a feature called HTTP Redirection. When you change a setting at the Default Web Site, those settings are pushed down to the virtual directories below that, so you need to fix the virtual directories below after making the change at the top level.

  1. In IIS select the Default Web Site.
  2. Open the HTTP Redirect option on the right side.
  3. On the HTTP Redirect, set the settings as shown
  4. Disable the redirect for the following virtual directories
    1. aspnet_client
    2. Autodiscover
    3. ecp
    4. EWS
    5. Microsoft-Server-ActiveSync
    6. OAB
    7. PowerShell
    8. Rpc
  5. On the Default Web Site, click on the SSL settings, and uncheck the “Require SSL” checkbox.
  6. On the following virtual directories check the “Require SSL” checkbox.
    1. Autodiscover
    2. ecp
    3. EWS
    4. Microsoft-Server-ActiveSync
    5. OAB
    6. owa
    7. Rpc


**Thanks to Brian Desmond for a lot of this information.

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