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When you use the Server ActiveSync component of Microsoft Mobile Information Server to synchronize the Inbox, the Calendar, or the Contacts on your mobile device with the server that is running Microsoft Exchange 2000 Server, you may receive the following error message on the device:
Synchronization failed due to an error on the server. Try again. HTTP_500
This problem can occur if the Exchange virtual directory on the server that is running Exchange 2000 Server is configured to require Secure Sockets Layer (SSL). Server ActiveSync communicates with the server that is running Exchange 2000 Server over port 80.
To work around this problem, verify that SSL is not required on the Exchange virtual root. To do this, follow these steps:
On the server that is running Exchange 2000 Server, click Start, point to Programs, point to Administrative Tools, and then click Internet Services Manager.
Expand the ServerName and the Default Web Site nodes.
Right-click the Exchange virtual root, and then click Properties.
On the Directory Security tab, click Edit under Secure Communications.
Verify that the Require Secure Channel (SSL) check box is not selected, and then click OK two times.
Close Internet Services Manager.
Microsoft has confirmed that this is a problem in the Microsoft products that are listed at the beginning of this article.