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KindleGen will always "work" you'll just get mobi file that will not have working "Go To" option on older Kindle models (Kindle 2, Kindle 3...) that use HTML ToC for that (Kindlegen will show a warning that it can't find HTML ToC). Those models use NCX ToC only for showing those chapter markings on progress bar at the bottom of screen, and for skiping chapter forward/backward using D-Pad, but Go To option just goes to HTML ToC.
Newer models (Paperwhite...) use NCX ToC for Go To menu, just like any epub reader device.
No idea if newer versions of KindleGen & Kindle Previewer have maybe added functionality of automatically creating HTML ToC from NCX ToC and set semantics... I haven't used Kindlegen for at least 2-3 years.
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