VMware Tools does not install on a Windows 2008 guest operating system after upgrading to ESX 4
You must perform a forced uninstall and install of VMware Tools.
To uninstall and re-install VMware Tools:
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Right-click on the virtual machine you are having an issue with.
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Click Guest > Install/Upgrade VMware Tools.
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Open a Console to the virtual machine and log into the guest operating system.
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Ope the Command Prompt in Windows and change the drive to your CD-ROM drive.
For example, D:/
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Type setup /c and press Enter to force removal of all registry entries and delete the old version of VMware Tools.
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In My Computer, double click the CD-ROM that contains VMware Tools.
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After Auto-Run starts, follow the prompts to install.
Note: This must be done from the GUI interface, do not launch the install by running Setup from the Command Prompt.
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When the installation is complete, reboot the guest operating system.