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Is there a way to re-sync my entire Outlook calendar onto my BB?
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No, after an activation, messages and calendar entries are only populated for a certain amount of time in the past ("Prepopulation").
You have to consider the Blackberry as a tool to manage the most recent stuff. Holding everything for an indefinite amount of time would exceed the memory capabilities of the device.
You could try the following (but it will probably not bring back more than 30 days, haven't tested myself):
In your calendar, go to options and type rset
This will erase and resync you calendar.