That's not the issue - I have about 630GB free on the HD overall (1TB HD). I have only one VM.
Hi CayleyR, if your VM is only occupying 101GB in 256GB allocated and giving you no space alert means there is no space on the Mac side. Windows can occupy upto 256 GB if there space on Mac. Once you have free space on Mac, launch Windows and check the size of C drive then let us know.