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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!
MORE INFO FROM ADDITIONAL TESTING:
2 MS Word Documents: 1st: 2100 pages, 16MB, 2nd: 1700 pages, 12MB
With NO hyperlinks in TOC:
WITH hyperlinks in TOC to headers IN SAME DOCUMENT (no hyperlinks to external docs):
I'd say this is not necessarily a "Mac issue" exclusively but clearly Word for Mac and Word Web appear 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
A family of Microsoft word processing software products for creating web, email, and print documents.
Try creating a new user account in System Settings>Users & Groups. Then sign in to that account and see if the problem still exists. If it's still there, or if you don't want to switch accounts, try uninstalling Office for Mac using these steps, then reinstall from the Subscriptions page of your Microsoft account.
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Hi Bennie,
This isn’t a one-off issue it’s a known limitation in Word for Mac and Word Web when handling large documents with active TOC hyperlinks. Microsoft hasn’t published a definitive fix yet, but using Word for Windows or splitting the document are the most reliable workarounds for now.
Windows Word, on the other hand, handles this locally with more robust PDF rendering capabilities, which is why it succeeds even with large documents and active TOC links.
Workarounds You Can Try
Split the Document Temporarily
If feasible, split the document into smaller chunks (e.g., <600 pages), export each with hyperlinks, then merge the PDFs using a tool like Adobe Acrobat or Preview on Mac.
Use Word for Windows for Final Export
If you have access to a Windows machine, open the document there and export with hyperlinks enabled. This avoids the limitations seen on Mac/Web.
Print to PDF with Hyperlinks (Advanced)
On Mac, printing to PDF doesn’t preserve TOC hyperlinks unless “Best for electronic distribution” is selected which isn’t available in your case. However, you might try:
Saving the document as a web page (.htm), then opening it in a browser and printing to PDF.
Or using third-party PDF tools that preserve internal links during conversion.
Let me know how it goes, Happy to help!