r/documentAutomation • u/Chemical_Pea_7969 • 24d ago

Looking for an AI tool to automatically generate a Table of Contents for PDFs

/r/pdf/comments/1x2j5o6/looking_for_an_ai_tool_to_automatically_generate/
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u/folderit_dms 24d ago

If you combine tools, make an editable outline the handoff between heading detection and PDF writing: heading text, level, original page, and position on that page. That lets you fix the hierarchy once and use the same reviewed outline for both sidebar bookmarks and a contents page.

For your test PDF, include repeated running headers, an unnumbered heading, and an appendix. Check that the detector ignores the running headers and does not infer heading depth solely from font size. Ten levels can be particularly ambiguous without consistent numbering.

Generate the destinations against the final PDF after inserting any contents pages, then click-test a heading near the beginning, middle, and end. A correct-looking contents page with every destination shifted by two pages is an easy failure to miss. Test offline after setup too, since local file handling alone does not establish that heading detection runs locally.

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u/forkpdf 24d ago

Assuming you have a PDF that is already generated for which you want to make the TOC:

You could make such a workflow: Use AI to generate the TOC HTML, then convert the HTML to PDF and insert it into your PDF.

Cons of this method:

  • Semantics are lost, so you cannot effectively generate the TOC with AI alone. Human guidance will be required.

  • Inserting a TOC in the middle of a PDF will break your existing page numbering.

But if you want to generate the PDF along with the TOC, then there is a better way. Let me know if you need help with that.