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Yes, I use MS Word's built-in chapter heading Styles, Heading 1 and Heading 2 and create the Table of Contents with MS Word's Table of Contents Wizard.
Then I save my Word file as "Web Page, Filtered", and import that HTML file into Calibre.
Calibre appears to be using my Table of Contents to build the Table of Contents that it puts in the end of the mobi file.
The reason I think that is, that if I don't add a Table of Contents to the front of my file, Calibre won't add one to the end of the file.
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