Symptoms:
When installing or upgrading VMware Tools to 10.3.x in Windows guest, you may experience one or more of these symptoms:

• Installing or upgrading of VMware Tools to 10.3.x fails, if Windows OS level prerequisites are not met.
• Installation progress holds up for several minutes with the message:

  "Preparing 'VMware Tools' for installation..."

When installing or upgrading Workstation 15.5 in Windows, you may experience one or more of these symptoms:

• Installing or upgrading of Workstation 15.5 fails, if Windows OS level prerequisites are not met.
• Installation progress holds up for several minutes with the message:

  "Preparing 'VMware Workstation' for installation..."

For both VMware Tools and Workstation you may experience the symptom:

• Prompts for a system restarts, possibly twice on 64 bit systems, without completing the install or upgrade.

VMware Workstation Pro 15.x (Windows)
VMware Workstation Player 15.x (Windows)

VMware Tools 10.3.x and Workstation 15.5 depends on and ships Microsoft Visual C++ 2017 Redistributable version 14.x. While preparing the system for VMware Tools 10.3.x or Workstation 15.5 installation, Microsoft Visual C++ 2017 Redistributable is installed on the system as a prerequisite. This requires Windows operating system to be at certain service pack level. Also, Microsoft Visual C++ 2017 Redistributable includes Windows Update. Installing Windows Update on the system may take a while and may also need a system restart depending on the state of the system.

For more information, see the Microsoft article:

• Update for Universal C Runtime in Windows
• Stuck while installing Visual Studio 2015 (Update for Microsoft Windows KB2999226)

Note: This issue applies to only Windows Vista, Windows 7, Windows 8, Windows 8.1, Windows Server 2008, Windows Server 2008 R2, Windows Server 2012, Windows Server 2012 R2, Windows 10 and Windows Server 2016 and newer.

Windows operating system restart may be needed for different reasons, for versions earlier than Windows 10, it could be either due to missing Windows update (see KB2999226 ) or due to presence of an existing older version of Microsoft Visual C++ 2017 Redistributable DLL on the system that is already loaded by other applications. For Windows 10, Windows Server 2016 and later, the latter reason is a common cause of system restart.

Windows OS level prerequisites:
 

Windows Server 2016

Windows 10

Windows Server 2012 R2 with Microsoft update (KB2919355)

Windows 8.1 with Microsoft update (KB2919355)

Windows Server 2012

Windows 8

Windows Server 2008 R2 Service Pack 1 (SP1)

Windows 7 SP1

Windows Server 2008 Service Pack 2 (SP2)

Windows Vista SP2

This is a known issue affecting VMware Tools 10.3.x for Windows and VMware Workstation 15.5.

Resolution when issue affecting VMware Tools 10.3.x for Windows:

Installing or upgrading VMware Tools 10.3.x is not supported for Windows versions that do not meet prerequisites and you should continue to use VMware Tools 10.2.x or older until you can update Windows OS to meet the prerequisites for VMware Tools 10.3.x.

Resolution when issue affecting VMware Workstation 15.5:

Installing or upgrading Workstation 15.5 is not supported for Windows versions that do not meet prerequisites and you should continue to use Workstation 15.0.x or Workstation 14.1.x until you can update Windows OS to meet the prerequisites for Workstation 15.5.

Workaround:
To workaround this issue, use one of these options:

• Upgrade Windows with latest service pack available from Microsoft and install the Microsoft Visual C++ 2017 Redistributable manually before installing or upgrading to VMware Tools 10.3.x or before installing or upgrading to Workstation 15.5.
  
  Note: If installing Microsoft Visual C++ 2017 Redistributable is not possible, consider installing the Windows Update manually to reduce the need for system restart in versions earlier to Windows 10.
• When VMware Tools installation or upgrade is invoked with REBOOT=ReallySuppress argument and a system restart is required for completing Microsoft Visual C++ 2017 Redistributable install, re-attempt the VMware Tools installation or upgrade after restarting the Windows system. vSphere client can detect this situation by noticing no change in VMware Tools version and guestinfo.toolsInstallErrCode=3010 in the guest variables or in the advanced configuration of the virtual machine.
  
  Note: When the VMware Tools installation or upgrade is invoked without any arguments, a system restart may occur automatically to complete Microsoft Visual C++ 2017 Redistributable install. After Windows system restarts, re-attempt the VMware Tools installation or upgrade.