Adobe Acrobat Pro DC crashes when compressing uncompressed objects during preflight of 2 files.

On one occasion it said unable to save. An I/O error has occurred.

Most of the time it crashes without erring.
I did change the file to a new file name and it still crashed. I got new files from my client thinking they may have been corrupt files and the same thing happens.

Acrobat DC is up to date vs 2020.013.20074
Mac Catalina Vs. 10.15.7

This is only occurring when I preflight to my network drive and not my local machine. I found a workaround to preflight them to my local machine but this is not optimal. The other applications on my machine are not having issues saving to my network drive it seems to only occur during the preflight in Adobe.