In the Connection tab of the Vinyl Spooler set the Port Type to Windows and the Port to FILE: Then, with the cutfile in question selected in the Vinyl Spooler, click Cut Now and instead of sending the file directly to the cutter, a window will appear, asking you to save the data to a PLT file on your computer.
Save this file and email it to support@future.support and they will take a look at the file to see if it is hardware or software related.