Just thought I would mention I am using Calibre 0.8.5 and iTunes 10.5 on Windows 7 and it is connecting and syncing with no issues. I still only have iOS4.3 on my iPad (at the moment), but that should not be relevant to the iTunes/Calibre interactions. Therefore if there is an issue between Calibre and iTunes 10.5 it looks like it might be specific to OSX?
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