VMware Tools Installation Failure on Windows Server 2016 VM

Products

• VMware vSphere ESXi
• VMware vCenter Server

Issue/Introduction

 

This article provides the resolution for an issue where the VMware Tools installation fails on a Windows Server 2016 production virtual machine due to RDP clipboard redirection settings preventing file transfers during the installation process.

• Manual installation of VMware Tools fails on the virtual machine.

• Unable to copy or paste files from the local system into the RDP session.

• Attempts to transfer the VMware Tools installer to the VM are unsuccessful.

 

Environment

VMware vSphere / vCenter 7.x & 8.x 

Cause

The issue occurs because RDP clipboard redirection was enabled, which restricts copy/paste and file transfer functionality within Remote Desktop sessions.

 

Resolution

To resolve this issue, modify the Group Policy settings to allow clipboard redirection and enable file transfers in RDP Machine.

Steps:

1. Press Win + R, type gpedit.msc, and press Enter to open the Local Group Policy Editor.

2. Navigate to: Computer Configuration → Administrative Templates → Windows Components → Remote Desktop Services → Remote Desktop Session Host → Device and Resource Redirection

3. Locate and double-click Do not allow clipboard redirection.

4. Set the policy to Disabled or Not Configured.

5. Click Apply, then OK.

6. Restart the server to apply the changes.

7. After the restart, copy the installer file “VMware-tools-13.0.0-24696409-x64.exe” into the VM via RDP and proceed with installation.

Additional Information

The clipboard redirection policy in the RDP configuration was enabled, which blocked all copy/paste and file transfer actions between the client and the server. Disabling this policy should restore clipboard functionality, enabling successful transfer and installation of VMware Tools.