I'm seeing the same symptoms as Neil too. (On OS X 10.6.3)
The book gets sent to the iPad, but Calibre then sits there trying to send metadata to the device forever (like 10 minutes, before I gave up). It won't let me cancel the job, but I can quit Calibre and all is well on the iPad, but in Calibre the "On Device" and "In Library" columns never get updated.
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