Upgrading VMware Tools: From a Simple Routine to an Unexpected Challenge

The Plan

Last Tuesday, I had one of those “routine” tasks on my list: upgrade VMware Tools.

On paper — quick, easy, done in minutes.

But if you’ve been in system administration long enough, you know:

“Simple” doesn’t always mean “smooth.”

The Problem

One of my servers needed to go from version 9345 to 12389 with a single click.

Instead, I kept facing the same frustrating error — both in automatic and manual mode:

The feature you are trying to use is on a network resource that is unavailable. Click Ok to try again, or enter an alternative path to a folder containing the installation package 'VMwareTools64.msi' in the box below.!

This error means part of the existing installation is missing or corrupted, and the upgrade process simply won’t run without it.

What Usually Happens

Years ago, VMware provided a tool called VMware Tools Cleanup Utility for such cases.

But it’s no longer available from official or trusted sources.

And while third‑party uninstallers exist, they often leave behind files, registry entries, and services that keep causing issues.

So in my opinion, the most reliable fix in this situation is:

Manually remove VMware Tools completely, then do a fresh install.

My Cleanup Process

1. Stop the Service

Stop the VMware Tools service.

2. Delete Installation Files

Go to the default installation path:

Then delete all VMware Tools files.

Here’s the exact list of files and folders I removed:

(Pro tip: double‑check file deletions, especially on production systems.)

3. Remove Registry Keys

Delete these registry entries carefully:

4. Restart the Server

Pro Tip: Watch the VSS Service

Before installing the new version, always check that the

Volume Shadow Copy Service (VSS) is running.

If it’s set to Not Running, VMware Tools installation can fail halfway through.

This is a common but often overlooked cause of installation errors.

Final Thoughts

After following the above steps, the new version installed without a single complaint.

Hopefully, this saves someone a few hours of frustration.

If you’ve found a better or cleaner method — I’m all ears!

#VMware #WindowsServer #IT #SystemAdmin#Troubleshooting