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I don't know if this is still an issue or not, but when cloud collections were first introduced, they did sometimes cause your collections to disappear if you created them with WiFi off and then turned on WiFi.
As it stands now, collections on new Kindles have to be created manually and populated manually. There is no way to get Calibre to do it for you like you can on Kobo Readers. Amazon originally allowed computer control of collections and then for some unknown reason, took that feature away.
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