Here's an interesting issue I came across recently. We're starting to see our customers deploy Windows Server 2008 VM's in greater numbers, and this is an issue you might come across as well.

After upgrading an ESX 3.5 environment to vSphere 4, using VMware Update Manager to push the new VMware Tools to a Windows Server 2008 guest fails to properly install. A manual installation attempt fails as well. VMware has documented the solution <a href="http://kb.vmware.com/selfservice/microsites/search.do?language=en_US&amp;cmd=displayKC&amp;externalId=1012693">here</a>.

To resolve this you must perform a forced uninstall and install of VMware Tools on the client.

To uninstall and re-install VMware Tools:
<ul>
	<li>Right-click on the virtual machine you are having an issue with.</li>
	<li>Click Guest &gt; Install/Upgrade VMware Tools.</li>
	<li>Open a Console to the virtual machine and log into the guest operating system.</li>
	<li>Ope the Command Prompt in Windows and change the drive to your CD-ROM drive.</li>
</ul>
<p style="padding-left: 60px;">For example, D:</p>

<ul>
	<li>Type setup /c and press Enter to force removal of all registry entries and delete the old version of VMware Tools.</li>
	<li>In My Computer, double click the CD-ROM that contains VMware Tools.</li>
	<li>After Auto-Run starts, follow the prompts to install.</li>
</ul>
Note: This must be done from the GUI interface, do not launch the install by running Setup from the Command Prompt.

When the installation is complete, reboot the guest operating system.