Instructions to enable the debug logging: 
1.       Right click on application shortcut to bring up Properties.
The “Target” field will be something like

"C:\Program Files (x86)\Prime Technologies\ProCal V5\ProCalV5.exe"
Including the quote characters.
2.       Change the whole target field to:
"C:\Program Files (x86)\Fluke\ProCal V5\ProCalV5.exe" "-debug"
Please note the space between the “ after .exe and the “ before "-debug".
3.       Save the shortcut.
4.       Retry the operation again using this calibrator.
5.       After you try it you should see a log file in one of two places:
C:\Program Files (x86)\Prime Technologies\ProCal V5\ProCalV5.exeLOG.txt
C:\Users\<your username>\AppData\Local\VirtualStore\Prime Technologies\ProCal V5\ProCalV5.exeLOG.txt
When this is run this way and an upload is run this same folder will contain a number of log files e.g. 020200415_122027_DEBUG.txt, which are basically a sequence number followed by the date and tie and then _DEBUG for debugging purposes.