There could be a corrupted entry somewhere. You might check the sync settings for what wins on conflict. I have mine set to ask if there is a conflict. Also if you have multiple email accounts set up on the devices, there is a calendar for each one. Make sure you have the one you want to sync with set as default. I was 'losing' some appointments on my calendar when syncing -- then I found the wrong calendar was set to default somehow and the appointments were on that one.
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