Можно попытаться выполнить эту команду на подсказке:
c:\windows\system32\cscript.exe c:\windows\system32\iisapp.vbs
I totally forgot to update this =D.
My solution ended up being querying the local print queue on the workstation.
CSCRIPT "C:\WINDOWS\system32\PRNJOBS.vbs" -l ^| FIND /I "printed file"
Running that queries the local print jobs with their file names, then I search for the file in the output to see if it successfully made it to the print queue. This is the closest that I could come to my solution and it has been working thusfar.