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I've just set a new server with BES 5.0 and ZCB 6.5 beta build #5387. I've activated a few phones for testing and I'm having problems when a calendar appointment is created on the device, it will not sync back to the users account. If the appointment is made in the web client it will sync to their blackberry.
Can you please post the version and size of emsmdb32.dll from BES machine? Also do you see offending appointments if you stop BB controller and open up 'BlackBerryServer' profile with Outlook?
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ZCB 6.5 build #5387 BES 5 Calendar Issues 
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