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One way that it WILL work and I speak from experience... have Calibre convert your Mobi file to an epub -this will result in an inline Table of Contents (HTML).
Download a copy of Kindle Previewer (for Mac) from Amazon. Drag your epub into Previewer and it will do another mobi conversion. And your Table of Contents built by Calibre/Previewer should work on Previewer. You can then upload to Amazon and it WILL have room for the DRM on your newly created mobi.
Good Luck!
Lazer
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