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I just checked again: calibre has not yet added a driver for Kindle Touch. As such, I would not trust it to put content on KT. There have been some changes to how Amazon organizes the content (specifically where it puts sidecar files) and I think calibre needs to take that into account. The Kindle plugin is pretty much useless for KT as well.
Even before this, I was using calibre less and less to put content on my Kindle, because of the improvements to the Personal Documents service, which lets me put everything in the free account cloud storage. So I use the calibre email to kindle feature instead. Then I get syncing, notes backup, etc.
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