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!

Have you tried it on another Mac, or on a PC?

Are there external link references in the pages that get deleted when he reduces the size of his document <600 pages? For example, links to other documents, images or Excel files, or even hyperlinks to pages on an intranet.

__________________
Cheers,
Paul Edstein
[Fmr MS MVP - Word]

@macropod - thanks for your input

Yes - works on a PC with no issues but a different mac on a different internet connection gives the timeout.
There are no external links in this document, the hyperlinks are TOC hyperlinks to headers in the same document. When the document is reduced in size, it also reduces the number of hyperlinks in the TOC

Can the document be placed on OneDrive and printed using the web app? That gives a pdf.

If there are no external links, a different internet connection shouldn't matter.

__________________
Cheers,
Paul Edstein
[Fmr MS MVP - Word]

@charles kenyon - good question. Will add that to my test scenarios to try.

@macropod - I don't know this for a fact, but my understanding is that word (maybe only mac version of word) connects back to adobe to do the export when hyperlinks are involved. This is a vague memory of something I read somewhere. It most definitely is giving an error related to "Internet access" when the he exports a large word document with in-document hyperlinks in the TOC

Just tried - got the below error - will try again later but not optimistic. Great idea, though.

Sorry, your document could not be converted.
Try again later or print using Microsoft word.

That doesn't really make sense, since the implication is that Word - which doesn't need Adobe - couldn't save a document as a pdf without an internet connection.

__________________
Cheers,
Paul Edstein
[Fmr MS MVP - Word]

Thanks for the reply. I don't disagree but: 1) the failure only happens when export with hyperlinks activated in TOC (on Mac only, doesn't fail on PC) and the failure clearly indicates an internet issue; 2) I've a few post in forums indicating there is some library MS Word wants to access to do the export - but, again, since this doesn't happen on my PC I'm not up to speed on what's happening behind the curtain

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