Links are not working after converting a Word document to a PDF. After much troubleshooting, the cause of the issue is the number of pages. Four or more pages works as expected, three or less does not.

To reproduce the issue, create a Table of Contents at the top of the document that links to the Headers of each section. Then Save As Adobe PDF. The expected result is that the Table of Contents will still contain links to the Headers of each section as bookmarks in the new PDF. The observed result is that the links are broken if the document is less than four pages in length. I am using Windows 10/Office16/Adobe Acrobat Pro DC Version 2021.007.20095.

A workaround is to add blank pages to the shorter document to make it at least four pages. This will allow the links to carry over in the conversion. The pages can then be deleted directly from the PDF and the bookmarks will stay. However, this is not an ideal long-term solution.

In the attached documents the only change I made between the two PDFs was to add a blank page at the end.