Why does the multiple file "create PDF" function fail to completely export a file?

I'm having a specific problem of when I click on "create multiple PDF from multiple files" where some of my files have a mix of portrait and landscape view pages. The problem occurs on the page where there is a landscape page. The export stops at this page. Meaning instead of a 20-page document I only have 10 pages (since page 10 is the beginning of the landscape document.

I originally thought it might have to do with the word doc being a cloud doc in one drive (which does have its own issues specifically related to this function). So, I downloaded the files to my hard drive and no luck. I then uploaded the word docs to creative cloud, no luck again. Then I tried exporting these files directly form MS word to see if there was a problem, but there were no issues doing it this way. Which tell me there is an error in how these multiple files are processed via Abode's software.

Can someone see if they can replicate this problem? I'm using Mac OS High Sierra and below is my word for Mac Version.