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This may occur for various reasons depending on the version of Exchange Server that you are running. But most typically, the cause is configuration changes that occur in Internet Information Server (IIS) or in the permissions of the OWA directories.
I have found that a reapplication of the latest service pack usually corrects the problem, or sometimes even a simple reboot of the Exchange Server. You can also check out the Microsoft Knowledge Base article 298513, "Removal of application mappings may cause an HTTP 404 error in Outlook Web Access."
Do you have comments on this Ask the Expert Q&A? Let us know.
Related information from SearchExchange.com:
Tip: Recreating IIS virtual directories for OWA
Tip: IIS troubleshooting tips
Step-by-Step Guide: How to repair Exchange-related IIS virtual directories
Administration Guide: Outlook Web Access
Reference Center: Exchange Server and IIS interoperability resources
Reference Center: Outlook Web Access tips and resources
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