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Originally Posted by gandoe
I have successfully used Calibre Sync (CS) to connect to my Calibre library using the Calibre Content server, which allows me to download the entire metadata DB and perform various filter and download actions. I typically download only a small selection of books to my device at any one time. But, connecting this way does not change Calibre behavior to indicate which files are actually on my device.
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Correct, with the Content Server Calibre doesn't indicate the files on your phone - sure, Calibre is not connected to your phone! By the way, WebDav/OPDS does not show you the books on your phone in Calibre either.
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I also connected via Calibre Wireless Connect, which does change Calibre behavior, including "Wireless Device: Calibre Sync detected", and in the Calibre itself, a new column "On Device" appears. However, this column is completely blank, with no indication of what files are on my device. I have set the inbox directory to the same directory that I had downloaded ebooks using the Calibre Content Server connect method. When I connect as Wireless Device, there are no books that are displayed in CS. I would have thought it would display the files on my device?
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I don't know what you did, but it worked perfectly for me on iOS, including indication of the books on my phone. Forgive me for asking this stupid question, but you've already sent some books to the device, haven't you?
For your use case, I would actually rely on Smart Device and set up a custom column in Calibre in which I enter which book is on which device and keep it up to date.
Edit: I think you could also automate this with the Reading List plugin, but I'm not that familiar with it