Help please - when printing to adobe pdf, this hangs and stays in spool status

Can someone help assist and troubleshoot this problem I'm facing with printing to pdf.
The background is I provided a vendor a Word converted PDF document approval letter to upload into the system.  While UAT testing, we are not able to print to PDF - hangs in print spool.
However the document checklist that had been uploaded into the system, properly prints to pdf (see page 2 attached).  Is there any way to debug or determine the root cause since the vendor believes that they have delivered a product that works from their perspective and suggest it's an Adobe issue.

Hi,
Could you please provide both the word documents(one that prints and the other that does not print) ? This would be helpful in isolating the issue.
Thanks,
Swati
[email protected]

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