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Avoiding a prompt for credentials when using Outlook Anywhere

Outlook Anywhere (formerly RPC over HTTP) is a fantastic feature that allows Exchange users to use Outlook in an environment where traditionally only a POP3 or IMAP solution could be used. There are many articles detailing how to configure Outlook 2010, but fewer that detail how to configure older versions of Outlook. Although the following procedures have been tested for connecting to an Exchange 2010 server, the principles hold true for Exchange 2007.

This article only refers to the client side setup and presumes that Outlook Anywhere has been configured and is working on the server. This is achieved by ensuring the following requirements have been met:

  1. Outlook Anywhere is enabled on the Exchange server
  2. Valid DNS records exist for autodiscover.domainname.com and an external FQDN
  3. A valid certificate is present on the OWA website (not self signed)
  4. Firewall or router passes SSL traffic to OWA website

In the steps below, the user’s email address is different from their user logon account (email address is givenname.surname@domainname.com and the logon account is GSurname@domain.local or NETBIOSGSurname). Outlook 2010 doesn’t present any issues and is only included here to illustrate where previous Outlook versions differ.

Outlook 2010
 

Configure the Outlook client
  • An autodiscover record is required
  • Enter the end user’s actual email address, not the username of their logon account
  • Enter the password twice (although this won’t be used if the username and email address differ)
  • When prompted during configuration, supply the logon account Username and Password using NETBIOSUsername or Username@internal.local three times but don’t bother selecting the option to save credentials as they won’t be saved. If the email address and username are the same, there will be no prompts and the configuration will immediately go to the Finish screen
Run Outlook
  • When launching Outlook, you are prompted for your credentials to connect to Exchange
  • Supply the credentials and select the option to save them

Outlook 2007
 

Configure Outlook client
  • An autodiscover record is required
  • Enter the end user’s actual email address, not the username of their logon account
  • Enter the password twice (although this won’t be used if the username and email address differ)
  • When prompted during configuration, supply the logon account Username and Password using NETBIOSUsername or Username@internal.local three times but don’t bother selecting the option to save credentials as they won’t be saved. If the email address and username are the same, there will be no prompts and the configuration will immediately go to the Finish screen
  • In Account Settings, Select the Exchange account under the E-Mail tab and click Change. This can be done within Outlook or from the Mail Control Panel applet
  • Select More Settings, then the Connection tab and click on Exchange Proxy Settings
  • Change Proxy authentication from Basic to NTLM authentication. This adds the option to save credentials when connecting to the Exchange Server
Run Outlook
  • When launching Outlook, you will be prompted for your credentials to connect to Exchange
  • Supply the logon account Username and Password using NETBIOSUsername or Username@internal.local and select Remember my Password
  • The saved credentials are stored as SERVERNAME.internal.local in the Credential Manager (in Control Panel) for Windows 7 or the Stored User Names and Passwords (Control Panel, User Accounts, Username, Manage my network passwords) in Windows XP

Outlook 2003
 

Configure Outlook client
  • Outlook Anywhere for Outlook 2003 requires Office SP2 to be installed
  • Either Launch Outlook or add an email account from the Mail Control Panel applet
  • Add an Exchange account
  • Supply the internal name of the Exchange server e.g. SERVERNAME.internal.local and the users mailbox name e.g. givenname surname
  • Hit More settings and dismiss the error message that pop up telling you that it can’t look up your name
  • Go to Connections tab and enable Exchange over Internet and hit the Exchange Proxy Settigns button
  • Add the external FQDN e.g. remote.domainname.com as the URL
  • Select SSL only and mutually authenticate to msstd: remote.domainname.com
  • Change Proxy authentication settings to NTLM Authentication
  • Click Okay, Next and Finish, dismissing any errors that may appear
Run Outlook
  • When launching Outlook, you will be prompted for your credentials to connect to Exchange
  • Supply the logon account Username and Password using NETBIOSUsername or Username@internal.local and select Remember my Password
  • The saved credentials are stored as SERVERNAME.internal.local in the Credential Manager (in Control Panel) for Windows 7 or the Stored User Names and Passwords (Control Panel, User Accounts, Username, Manage my network passwords) in Windows XP

 

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