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Send-to-device should automatically connect to attached ereaders and allow you to transfer books, but due to iOS updates it may not work with apple devices. I think it might work for iBooks, but you will still need the iOS Reader Applications plugin.
What app were you trying to send to on the iPad? For instance, Marvin will for sure not work.
Going from generic to Apple only sets the default conversion output profile (which affects conversion image scaling) -- calibre is able to connect to many devices as and when needed.
I suspect you did not actually connect to the iPad.
Have you ever used Connect-to-folder, and perhaps set it to auto-connect at startup?
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