To day I had a problem with starting the Calibre "Start Wireless Device Connection" and the Content Server.
It turned out to be a firewall problem.
But before I discovered that I turned on my spare desktop, that has a copy of Calibre and my Calibre database.
Here everything concerning connection between Calibre and CC was ok.
But not a single book in CC was registered as "On Device" in Calibre.
That is the "On Device" column in Calibre was totally empty.
The missing "On Device" registration is actually somewhat annoying.
I hope you find a solution.
Edit: I just want to mention that if I connect as Content server then it is correctly registered in CC whether a book is present on the device or not.
Last edited by svenlind; 06-13-2017 at 10:45 AM.
Reason: More info
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