Some text from a different post will help. I think I will add this to the FAQ.
Quote:
The content server is what is called a "pull" connection, which means you use your device to pull books from the server onto your device. Using the content server you can browse the books in your library from your device. CC puts a green check mark next to the book if it is already on your device. The wireless device is a "push" connection, which means that you use calibre (and talk to calibre) to push (send) books from your laptop to CC. There is no way on CC to ask calibre to send a book when wireless device connected.
When to use one or the other depends on what you are trying to do. The content server connection is often better for small operations such grabbing a book or a series. If your content server is set up appropriately then you can use it from anywhere in the world (the setup requires technical networking knowledge).
The wireless device connection is better for larger operations such as sending many books selected in calibre using a search. It is also the way to update the metadata for all the books on the device, something you should do if you change things in calibre such as covers, tags, comments, etc. Finally, it is the way that read information is (optionally) synced back to calibre.
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