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Entourage clients cannot synchronize with mailboxes that are located on a computer that is running Exchange Server 2007 Service Pack 1 (SP1) and Windows Server 2008. When an Entourage client tries to synchronize with the Exchange server, the Entourage client shows the Inbox. However, nothing is downloaded and the connection timesout.
This issue occurs because of some filter drivers of the file system that are used on the Exchange server. Moreover, Windows Server 2008 changes the behavior of the ReadFile function. This returns different values than in earlier Windows operating systems. However, Exchange Server 2007 SP1 is not aware of the change that causes this issue.
To resolve this problem, install Update Rollup 9 for Exchange 2007 Service Pack 1. For more information about Update Rollup 9 for Exchange Server 2007 Service Pack 1, see the following Exchange Help topic: