The issue:
After installing new Cumulative Update, VMware Workstation software cannot start. Furthermore, the following message is displayed:
VMware Workstation Pro can’t run on Windows
Check for an updated version of this app that runs on Windows.
Compatibility Assistant
Check for updates – Dismiss
Cause:
As part of Cumulative Update (September 26, 2019; OS Build 18362.387 or newer) installation, database of programs prohibited by MS was updated, and invasive “Compatibility Assistant” component now prevents older VMware Workstation programs from run.
How To Fix VMware Workstation Pro Can’t Run On Windows using The Windows Assessment and Deployment Kit (ADK) Without Uninstalling Updates
Step 1. First, click here to download the Windows ADK for Windows 10, version 1903.
The Windows Assessment and Deployment Kit (Windows ADK) has the tools you need to customize Windows images for large-scale deployment, and to test the quality and performance of your system, its added components, and the applications running on it.
Step 2. Install The Windows Assessment and Deployment Kit on your computer.
1. Once the file is downloaded, double the adksetup.exe file to install the Windows ADK on your computer.
2. When you start the installation, a Windows ADK setup wizard dialog box appears. Click Next to continue.
3. In this dialog box, you click Next to continue.
4. Now, you should see Licence Agreement dialog box. Click Accept to continue.
5. In this dialog box, you can select which features to install. Check “Application Compatibility Tools” option and click on the Install button.
6. After the installation of Windows ADK is complete, click Close to exit the installation.
Step 3. After that, click on Start Menu then type “Compatibility Administrator” and select “Compatibility Administrator (32-Bit or 64-Bit)” from the results.
Step 4. On the left-hand side, go to System Database > Applications. Then scroll down and search for Vmware Workstation Pro and click on it.
Step 5. On the right side, you will see two items: Vmware.exe and Vmplayer.exe. Disable these items by right-clicking on each and select Disable Entry.
Now you can try to open VMware Workstation Pro again and check if it works now.
VIDEO TUTORIAL: How to fix VMware Workstation Pro can’t run on Windows 10 1909
Hope something helps you.