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If you make heavy use of DeDRM (or other plugins that haven't been ported to Py3), may be best stick with 4.xx for now.
If you're using Windows 7, also want to stick with older versions.
My Kobo Aura HD connected fine after update. Occasionally a new firmware update will be incompatible with the current version of Calibre but there's an option to force it anyways. Hasn't ever broken anything on my end.
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