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I'm trying to put together a text-based PDF that will be read with a screen reader. In order to make the reading process as straightforward as possible I've used a hierarchy of three levels of headings. I originally created the document in Google Drive, but if I try to export a PDF from there all my headers disappear in the PDF document. If I export from Drive to Word then the headings are retained, but they disappear when I create a PDF from Word by using the built-in macOS PDF creation function.

How can I retain my headings when I create a PDF in macOS?

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  • Adobe Acrobat Pro may be the tool that will work for you. There is a free trial so you can experiment.
    – IconDaemon
    Commented Aug 22, 2020 at 20:00
  • Have a look at the Open Source alternative for Acrobat Pro called PDF Creator This might accomplish what you're looking for.
    – Allan
    Commented Aug 22, 2020 at 21:25
  • If you used the “export” function then have you tried creating the pdf from the print menu?
    – Solar Mike
    Commented Aug 23, 2020 at 5:34
  • What do you mean by "the headings disappear"? Are you talking about Table of Contents, or actual headings on the pages?
    – benwiggy
    Commented Aug 23, 2020 at 7:21
  • @benwiggy I think Adobe refers to these things as "tags". When you create, say, an HTML document with headers, in addition to visual styling the document includes invisible tags that are read by assistive technology like screenreaders. These tags disappear when creating a PDF in the way I described here.
    – Jim
    Commented Aug 23, 2020 at 14:34

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In Word for Mac 2019 (Version 16.41 (20081900) if I go to File -> Save As and choose File Format PDF it displays an option, "Best for electronic distribution and accessibility (uses Microsoft online service)". It then asked permission to use the online service. When testing in macOS Preview the Table of Contents shows Heading Two and Three assuming Heading One is the title. Setting an actual title with the title style now shows the Title and the 3 headings in the PDF table of contents.

So I think this will work without needing more advanced PDF tools such as Adobe Acrobat.

You might want to produce an actual Table of Contents in Word that might help as well but it wasn't necessary. I just applied the Heading Styles in Word to the headings and made the body portions the normal style.

Also in Word there is "Check Accessibility" under the Tools menu.

Tested doing same in Pages and that produces a table of contents with the style headings as well in PDF. But Word allowed for collapsing the headings while Pages generated the headings in a linear fashion in the table of contents.

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  • That works perfectly, thank you! And the ToC is very useful from an accessibility point of view, too. It seems that the Microsoft solution is the best one, so I'll use it for now. It's frustrating that there doesn't seem to be an open solution -- I did a bit more research, into things like pandoc, but nothing else seems to work.
    – Jim
    Commented Aug 23, 2020 at 14:36
  • Well I am sure that LaTeX would create suitable PDFs but there’s a somewhat steep learning curve. It’s best suited to templates that don’t change frequently. It’s all text and can use git for revision control. It’s a full typesetting system and the fact it can typeset mathematical formulas is only a small portion of its entire capabilities. The Pragmatic Programmer publisher produces all their books using only LaTeX. Because it’s all raw text you can treat it like source code. It’s also very easy to automate things.
    – James Brickley
    Commented Aug 23, 2020 at 15:57
  • Thanks, I'll try LaTeX; funnily enough I'm currently using it to typeset several tens of thousands of lines of poetry, so I know it well enough to do something like this EDIT: it looks like LaTeX may not be able to do it either: tex.stackexchange.com/a/533876/216326
    – Jim
    Commented Aug 23, 2020 at 17:47
  • Well that’s a bummer. I am sure they will solve it eventually. But having read up on what’s involved with a tagged fully accessible PDF it’s a rather large problem.
    – James Brickley
    Commented Aug 23, 2020 at 18:35
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    iso.org/standard/51502.html & iso.org/standard/54564.html are the official standards. blogs.adobe.com/accessibility/2012/08/pdf-ua.html
    – James Brickley
    Commented Aug 23, 2020 at 23:47

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