Microsoft Exchange and Blackberry Server Specialists

Outlook Anywhere

On This Page

  • Introduction - What is Outlook Anywhere?
  • Enable Outlook Anywhere using Exchange Management Console
  • Enable Outlook Anywhere using Exchange Management Shell
  • Change the Authentication Methods
  • Outlook Anywhere with a Wildcard Certificate
  • Reset the Outlook Anywhere Virtual Directory

Introduction - What is Outlook Anywhere?

Outlook Anywhere is a method for Outlook to connect to Exchange over the internet using the HTTPS protocol. By using HTTPS the session is secure. You need to use a trusted SSL certificate - the self signed certificate created during the installation of Exchange is not supported for use with Outlook Anywhere.

Enable Outlook Anywhere using Exchange Management Console

Outlook Anywhere is the new name for RPC over HTTPS which was first introduced with Exchange 2003, and is significantly easier to configure. It is a simple two step process.

  1. Open the Exchange Management Console and expand Server Configuration, Client Access.
  2. Right click on the server that you wish to Enable Outlook Anywhere on, and choose "Enable Outlook Anywhere...". You can also select it from the Action Pane on the right.

  3. A single window wizard will start. You need to external the EXTERNAL host name that the server responds to. Ideally this should match the common name on the SSL certificate.
    The authentication type can be set - the wizard only allows you to choose one or the other.
    Basic Authentication will cause an authentication prompt every time the client connects.
    NTLM Authentication will not cause an authentication prompt if the client is a member of the domain.
  4. Allow secure channel (SSL) offloading is not enabled in most deployments. It is used when something else is providing the SSL connection, such as an appliance.
    After making the selections, choose Enable.

  5. You will then get a Completion, which shows you the command that has been used to enable the feature.

  6. After approximately 15 minutes an entry will be made in the Application Event Viewer of the server indicating the feature has been configured.


Enabling Outlook Anywhere Using Exchange Management Shell

To enable the feature using EMS, use the following command:

Changing the Authentication Methods

If you want to support multiple authentication methods, then you need to change it through EMS.
However as you are changing an instance that is already configured, you need to include the identity.
Note - the client will have its authentication method set by Autodiscover, so if you change an Autodiscover enabled client, then it will be "corrected" at the next Autodiscover refresh.

You can find the identity by running the command

Outlook Anywhere with a Wildcard Certificate

If you are using a wildcard SSL certificate, rather than a unified communications certificate, then you need to make an additional configuration change:

Reset the Outlook Anywhere Virtual Directory

To reset the Outlook Anywhere virtual directory, follow these instructions:

  1. Disable Outlook Anywhere in Exchange from the same menu as step 1 above.
  2. Wait for the event log entry to appear indicating the option has been disabled.
  3. In Server Manager, remove "RPC over HTTP Proxy" from Windows Features.
  4. Once the remove wizard has completed, check in IIS manager for the two directories named RPC and RPCWithCert have been removed. If not, delete them.
  5. Run IISRESET to ensure the changes are written to the IIS metabase.
  6. Reinstall the RPC Over HTTP Proxy in Windows features.
  7. Enable Outlook Anywhere as per the instructions above.

If you are using SBS 2008, then you need to follow specific instructions for that version.