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they way it hangs, always at same place/same time, suggest that records which calibre or CC is trying to access on the Fire device may be corrupted or unreadable
is this timeout independent of what book or books you try to send ?
does it in fact time out just from connecting, before you try to transfer any books ?
are you using CC with connect to content server or connect as a wireless device, or have you tried both ?
is CC the current amazon app store version ?
have you tried clear cache & clear data in CC, then set it up again
and also to troubleshoot whether its calibre or CC, what happens if you don't use the app but try to transfer books from calibre to device using USB
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