Is each number text but tagged as a figure? If so, you should be able to just pull the text out of the figure tag and put it directly in the label tag.
The numbers should be text but are not tagged at all (don't show up in the tags panel as a separate tag). What does show is as an LBody tag with "Image (123): w:16: h:18 The right to inspect. . ." instead of simply "1. The right to inspect. . .". in the container. When viewed using the Edit PDF tool they appear as an image separate from the text. They also appear as slightly lower resolution with distortion around the edges. I've converted documents from Word that use the same multilevel list tool with associated styles, including another one just today, and it didn't have this problem. The settings were the same in both instances.
Using the Edit PDF tool:
Also, it is only the level-one numbers that are doing this. The level two (a.) and level three (i.) numbers are registering as text.
Ah, OK. I do not have Word 2016 yet, so I can not duplicate or suggest a great solution. My work-around approach would be ...
Use the Touch Up Reading Order tool to tag each of the image-numbers as a <Figure>. Add Actual Text to each Figure tag to represent the number. Nest each Figure tag in a Label tag. You will end up with something like this ...
I couldn't test it either, but have you tried to create your PDF with the built-in Export of Microsoft Word?
I just ran into the same issue on a document I was turning into a PDF. Both the multi level list numbering and the associated table of contents numbering came through as an image instead of text when converting to PDF.
Both the Adobe PDF creator and the Word Create PDF/XPS had the same issue.
Getting around it was very manual, but here it is...
Using this process, I converted the numbering into normal text:
(run this in Word with VBA: ActiveDocument.Range.ListFormat.ConvertNumbersToText)
The lists and table of contents were still a problem at this point.
Next, I used format painter to copy the style from good text to the misbehaving list numbers and table of contents.
Now the PDF was created correctly!
Neither this nor the tag solution above is perfect from an accessibility standpoint, but it is much better than how it originally comes through. I haven't found anything better yet...
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There is a super easy answer to this one my friend. I had that problem in Microsoft Word to Adobe 11 Pro and Adobe DC Pro. The answer is this:
1. Convert your Word .docx to a .doc BEFORE saving or exporting it to a PDF.
2. Save or convert your document to a PDF.
Magically, your numbers will become numbers, and other odd issues will disappear. Good luck my friend!! I've been remediating/working with Word and PDFs for 508 accessibility a LOT and I try to help others where I can.
Yes this solves the numbering problem.
But it also changes the layout of the document. not a surprise, because the document is blasted back to word 2003 version.
I found another solution here: Converting Automatic Numbering to Manual Numbering (Microsoft Word)
This solved the issue of exporting the numbering to pdf. But obviously this one has as drawback that I cannot auto-number any more.
Still looking for the right solution.
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I found a better way. Select each heading and then press Ctrl + Spacebar to remove any direct formatting. This will solve it.
Look here for more info: List number blurry, multilevel list - Microsoft Community