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Old Yesterday, 03:39 AM
blg56 blg56 is offline Mac OS Word 2019 - Can't Export to PDF with hyperlinked TOC Mac OS X Mac OS Word 2019 - Can't Export to PDF with hyperlinked TOC Office 2019
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Mac OS Word 2019 - Can't Export to PDF with hyperlinked TOC
 
Join Date: Oct 2025
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UPDATE 2025/10/24: After the suggestion to try MS WORD WEB, I've refined the results as follows:
2 MS Word Documents: 1st: 2100 pages, 16MB, 2nd: 1700 pages, 12MB
With NO hyperlinks in TOC:
- MacOS: both documents can be exported to PDF with no issues
- Windows/PC: both documents can be exported to PDF with no issues
- Word WEB: Export works for smaller (e.g. 1/2) document, fails to open for 2100 page document - still doing tests to see what size works
WITH hyperlinks in TOC to headers IN SAME DOCUMENT (no hyperlinks to external docs):
- MacOS: export to PDF of both documents fail around 650 pages in size (error indicates "internet problem"
- Windows/PC: no failures during export to PDF
- Word WEB: failure of PDF export fails at 1292 for first document - still have to test 2nd document

I'd say this is not necessarily a "Mac issue" exclusively but clearly Word for Mac appears to be doing something different for export to PDF that Word for Windows is not.

I feel like this is not a one off situation as I've seen multiple postings in various forums about this and similar issues but haven't seen any clear resolutions (other than making the document smaller which would be problematic as this goes from a 2 volume set of documents to 4+ documents).

Wondering if anyone else out there is currently seeing this issue - in particular on MacOS for files this size with hyperlinks in TOC.
Thanks

Quote:
Originally Posted by blg56 View Post
Hi,
I'm working with a friend who has WORD 2019 on Mac OS Ventura 13.6.9


He has a large docx file (2000+ pages, 15.7MB) which is exhibiting the following behavior:
- if his TOC does not have hyperlinks activated, he can export to PDF with no issues
- if he activates hyperlinks in the TOC (\h in field codes), the export times out with the error "can't export file". There was a problem connecting to the network" - this failure occurs after several minutes of apparent effort to export the document
- if he reduces the size of his document <600 pages, the export with hyperlinks works fine
- if he prints to PDF, he doesn't get an option for "best for electronic distribution" (hence, the hyperlinks are not active in the TOC)

Any suggestions appreciated on possible solutions.
Thanks!
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