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Newer Calibre conversions fail on Kindle

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I've been using Calibre for the better part of a year to update metadata and convert books to MOBI, and use Amazon's Send to Kindle (STK) app to transfer them to my Kindle Voyage. I've done it dozens of times and it always worked beautifully.

A month or so ago, the MOBIs stopped transferring to my Kindle even though nothing changed in my conversion workflow. The STK app reported the docs were successfully uploaded, but they just vanished in the cloud. I then decided to just e-mail the MOBI file to my kindle email address, and this also did not work.

Thinking the problem was with Amazon, I figured I would just transfer the MOBI directly via USB. Now, the MOBIs do appear in my Kindle library, but I get a vague error "Unable to open item" when I try to open them. I get the same error no matter from what type of document I have converted, including PDF, epub, and really basic HTML.

The problem does not seem to lie in the transfer process, as MOBIs that I converted prior to this issue are still able to transfer successfully. It's only newer conversions that are failing. There doesn't seem to be anything wrong with them, as I am able to open and view the MOBI in Calibre on my Mac.

I am using Calibre 2.82 for Mac OS and really appreciate any tips.

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