Host or Guest Update or Feature Upgrade? From which Feature version to which Feature version ... on Update on which Feature version of Windows 10 ... if this was Windows 10, you didn't say.

Either way, Windows probably broke something, perhaps it broke VMware Tools on the VM. If not, then VMware install on the Host. Just do a reinstall and see what happens.

In principle, this looks like VMware Tools getting broken because of Windows 10 Feature Upgrade on the Guest ... nothing new for that to break software, any software for that matter.