Kovid pointed to the list of suggestions for the Kobo devices, but we really need more information.
When the error message was displayed, there was a button on the message box to copy the full error to the clipboard. Press that and post the contents. That will give me a clue as to what is going on.
But, this shouldn't affect the state of the books already on the device. If you are losing the reading status of books after sending new books to the device, something else is wrong. It probably means the database on the device is corrupt and needs to be reset. But, I need the full error message to get a better idea.
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