I consider myself a lucky fellow, as I have managed to avoid any major issues (and even minor ones) when installing updates for Windows 10, both big and small ones (*knock on tree flesh*). Others have not been so fortunate. Microsoft's most recent cumulative updates have caused a few headaches around the web, from printer and sound issues, to even a missing Start menu. On top of it all, e can add a VMware Workstation bug to the growing infestation.
Microsoft is in a bit of a tricky spot, having to account for so many different hardware configurations. Problems will inevitably crop up. So in that regard, it is fair to cut Microsoft a bit of slack. At the same time, however, the number of annoying issues in such a short span is worthy of criticism.
As it pertains to the VMware Workstation issue, there are reports of cumulative update KB4517211 preventing it from running.
"I have discovered that my installation of three updates on Saturday September 28, 2019 has caused the failure of VMware Workstation Pro 14.1.7 to start. On Sunday, when I attempted to run VMware Workstation, it produced a Notification that said 'VMware Workstation Pro can't run on Windows'. Luckily, I was able to find that, when I uninstalled the three updates, it was the uninstallation of KB4517211 that allowed VMware to run," a user wrote on Microsoft's community forums.
This issue appears to affect both VMware Workstation Player and Pro, versions 12 and 14, on Windows 10 version 1903. I imagine Microsoft will eventually issue an official fix, maybe in the next cumulative update (and how knows that functionality that will break). In the meantime, if you rely on VMware Workstation, your best bet is to roll back the cumulative update.
How To Uninstall A Cumulative Update In Windows 10
You can do this by navigating to Settings > Update & Security. Click on View update history, then click the Uninstall updates link at the very top. Find the offending update, highlight it, and click the Uninstall button.
If you do not want to do that, there is another potential workaround posted on Tenforums. It involves manually replacing the sysmain.sdb file found in C:\Windows\apppatch. The user who posted the workaround also posted a replacement file, though you should always use caution with this sort of thing.