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How are you converting from Word to PDF? I generally get better results using the PDF Maker on the Acrobat tab as opposed to "Save as" PDF from the File tab. I also get better results if the Word document uses styles for headings, etc, and passes the Word accessibility checker with no errors or warnings. Also, using the most recent version available of both Word and Acrobat. Results vary though, and there is always some amount of accessibility cleanup work to do in Acrobat.
I am using PDF Maker from the Acrobat tab in Word 2010.
Most documents I receive are formatted using styles that are properly defined and applied. Word's accessibility checker usually comes up with two items which I solve in the PDF: one not inline cover color block (client requirement) that I artifact and Unclear Hyperlink Text which I add alt text for (though I could do this in Word).
I've tried conversion on an up-to-date Word 2010 at home and an unknown update status version at work. I use the same Acrobat DC cloud license in both locations, so no variables there. I would expect 80% good tagging with 20% cleanup, but am spending most of the time on cleanup.
In some documents it seems like the tags are three or so off of where they should be. For example, a paragraph that in Word was formatted as Body Text being tagged as Heading 1, but the actual Heading 1 is three tags up in the list and tagged not as a heading. The role mapping might show Heading 1 mapped as Paragraph, Article mapped as Paragraph, or Caption mapped as Heading 3, etc--it seems so random. Tables and lists show up correctly though, even complex types.
It is probably worth checking with our IT to see if there is a test computer with the latest Word. The results I am getting seem off base.
Yikes! Definitely worth trying a newer version of Word to see if you get better results, although I use both Word 2010 and 2015 and have not noticed a huge difference. A 20% on-average cleanup rate is a reasonable expectation, IMHO.
Ok, good to know my results are not typical!