You're trying to update VMware Tools on a Windows Server 2019 or 2022 VM, and it's been sitting on "Pending Restart" for hours. The update won't finish, and rebooting the VM doesn't help — it just comes back to the same screen. This usually happens after a Windows Update reboot was deferred, or when a previous VMware Tools install left a stale pending restart flag.
Why This Happens
VMware Tools installer checks the Windows registry for a reboot pending flag. That's at HKLM\SOFTWARE\Microsoft\Windows\CurrentVersion\Component Based Servicing\RebootPending. If Windows Update left that key there — even from a package that installed weeks ago — VMware Tools won't proceed. It's not a bug. It's VMware being cautious. But it's also annoying when you know a reboot won't fix anything.
The Fix
Here's the direct fix. Don't bother with reinstalling VMware Tools or running the installer in repair mode — it won't touch the registry flag. You need to clear that flag yourself.
- Open PowerShell as Administrator on the VM.
- Run this command to check if a reboot is pending:
Get-ItemProperty -Path "HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\Component Based Servicing" -Name RebootPending - If you get an error saying the property doesn't exist, the problem isn't here. Skip to step 6.
- If the property exists, delete it:
Remove-ItemProperty -Path "HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\Component Based Servicing" -Name RebootPending -Force - Also check and delete this key if it's there:
Remove-Item -Path "HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\Component Based Servicing\RebootPending" -Recurse -Force -ErrorAction SilentlyContinue - Now run VMware Tools setup again. It should proceed past the pending restart check.
- If it's still stuck, restart the Windows Update service:
Restart-Service wuauserv
Still Stuck?
Some older Windows Server 2012 R2 builds need a different approach. Check HKLM\SYSTEM\CurrentControlSet\Control\Session Manager\PendingFileRenameOperations. If that key has entries, VMware Tools sees them as pending reboots too. Clear the key's value (set it to empty) and retry.
Also worth checking — if you're running VMware Tools 12.x on a VM that was originally built with Tools 10.x, there's a known issue with the installer cache. In that case, uninstall VMware Tools from Programs and Features, reboot, then install the latest version from scratch.
One last thing — if this is a cluster of VMs, don't do this on all VMs at once. Do one, confirm the update finishes, then move to the next. I've seen the pending restart flag get recreated by group policy if you're not careful.
Prevention Tips
Patch Windows first, then update VMware Tools. That order avoids the flag conflict. Also, schedule VMware Tools updates when Windows Update isn't running — check with Get-WUInstall -ListOnly before you start.
If you're managing a vCenter environment, consider using the VMware Tools Lifecycle Manager to push updates centrally. But that's a separate tool — don't mix it with manual updates on the same VM.