I had a Windows 10 VM, created from a real PC using VMware Converter. The PC had one disk with two partitions. I couldn’t get VMware Fusion to shrink the disk.

I tried using Fusion on the host, going to General from the Settings for the VM. I told it to shrink the single VMDK (which had the two partitions in it). It wouldn’t shrink it below 240 GB.

Then I went to a CMD prompt in the guest, and I used

• VMwareToolboxCmd.exe disk shrink D:\

and I shrank my VMDK file down to 80 GB.