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Because calibre uses the kobo database to determine what is on the device, the kobo must "import" the book before calibre can see it. Importing happens when the kobo is disconnected; it tells you when it does that. Restarting the kobo seems to also trigger an import, as does resetting it.
I've read that a broken book can stop the import. That hasn't happened to me. If true then apparently you must receive books that never are imported. Others will have more info on this.
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