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First, make sure that this user has permission to access OWA. In Active Directory Users and Computers, select the Exchange Features tab of the user properties and verify that Outlook Web Access is enabled. Most likely, this is already enabled, but it's worth the check.
If OWA is in fact enabled, then try preceding the username with the domain name and a forward slash in the logon prompt. For example, instead of typing just JDoe, type MyDomain\JDoe -- obviously replacing the domain name and account name with the actual values.
If that still does not work, try resetting the password from the server. While this may seem somewhat odd, I have actually seen instances (on more than one occasion) where the user changed his/her password from a workstation, successfully logged onto the domain using the new password from the workstation, but couldn't access OWA. Resetting the password at the server actually fixed it. Strange but true.
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Related information from SearchExchange.com:
Expert Advice: Outlook Web Access permission problems
Expert Advice: Username and password logon problems in OWA
Tip: Troubleshooting OWA issues
FAQ: Outlook Web Access
Learning Center: Troubleshooting Outlook Web Access
Reference Center: Outlook Web Access tips and resources
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