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Originally Posted by JimLL
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Can anyone make a wild guess why this is happening?
I did one starting with a PDF last night that made a TOC. This morning I'm trying a different one but get no TOC...
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As Blossom said, this is really a calibre issue and not a MOBI/Kindle issue.
Basically, the issue is that the original file has to contain something that calibre recognizes at a "breakpoint" to use as a TOC anchor. Calibre is pre-programed with a reliable list of entities to detect, but they don't work with all files. The "Structure Detection" tab in the Convert dialog is where you can make customizations.