ActiveSync error: "HTTP Error 500 from Exchange Server"

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ActiveSync error: "HTTP Error 500 from Exchange Server"

Symptom
An ActiveSync mobile device is not successfully synchronizing and this error is shown on the Device details page on the administration website (fig.1.). The error shown on the mobile device will vary depending on the device being used.

Fig. 1

Explanation
This error means that the device has made a connection attempt to the Exchange server but the server has rejected that attempt with the message "HTTP error 500". This issue can occur if one of the below conditions is true:

Forms-based authentication is enabled on the Exchange server
Integrated Windows authentication is not enabled on the /Exchange virtual directory.
The /Exchange virtual directory in Microsoft Internet Information Server (IIS) is configured to accept only Secure Sockets Layer (SSL) connections.

The ActiveSync service within Exchange 2003 uses the /Exchange virtual directory to access OWA templates and DAV on the Exchange server on which the user's mailbox is located. ActiveSync cannot access this virtual directory if either of the above conditions is true. View this Microsoft article for more information.

Resolution

Create a second virtual directory for Exchange which does not require SSL. This will allow you to keep all settings are they currently are for standard connections, and the new virtual directory will only be used for ActiveSync connections.

See the Microsoft Technet article (scroll down to Resolution -> Method 2) on how to set this up or view the AccessMyLan KB article "How to create a second virtual directory for Exchange".

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