When managing Windows Server environments in virtualized infrastructures (especially VMware), the C: drive tends to accumulate massive amounts of patch-related files over time. Microsoft's official stance recommends against manually deleting compressed uninstall directories in \Windows, leaving administrators in a tough spot when dealing with hundreds of servers consuming expensive SAN storage.

While standard techniques like relocating page files and clearing temp folders help, let's explore more advanced approaches:

# PowerShell command to identify largest patch-related directories
Get-ChildItem -Path "C:\Windows" -Directory -Recurse -Force -ErrorAction SilentlyContinue | 
Where-Object { $_.Name -match "(ServicePack|KB\d+|Windows\d+.~\d+)" } |
Sort-Object -Property Length -Descending |
Select-Object -First 20 FullName, @{Name="SizeGB";Expression={[math]::Round($_.Length/1GB,2)}}

Instead of risky manual deletions, consider these Microsoft-approved methods:

# Using DISM for component store cleanup (Windows Server 2012 R2 and later)
DISM /Online /Cleanup-Image /StartComponentCleanup /ResetBase

# For Windows Server 2008 R2 (requires Desktop Experience feature):
cleanmgr /sageset:1 & cleanmgr /sagerun:1

For VMware environments specifically:

• Implement VM-level thin provisioning
• Use Storage vMotion to balance loads
• Consider NTFS compression for non-system directories

Here's a comprehensive cleanup script for scheduled tasks:

# ScheduledCleanup.ps1
$ErrorActionPreference = "SilentlyContinue"

# Clear temp locations
Remove-Item -Path "$env:TEMP\*" -Recurse -Force
Remove-Item -Path "C:\Windows\Temp\*" -Recurse -Force

# Clean IIS logs if present
if (Test-Path "C:\inetpub\logs\LogFiles") {
    Remove-Item -Path "C:\inetpub\logs\LogFiles\*" -Recurse -Force
}

# Clear Windows Update cache
Stop-Service -Name wuauserv -Force
Remove-Item -Path "C:\Windows\SoftwareDistribution\Download\*" -Recurse -Force
Start-Service -Name wuauserv

# Compact the Windows.edb file if search service exists
if (Get-Service -Name WSearch -ErrorAction SilentlyContinue) {
    esentutl /d "C:\ProgramData\Microsoft\Search\Data\Applications\Windows\Windows.edb"
}

For modern Windows Server deployments:

After managing hundreds of Windows servers in VMware environments, I've discovered that patch accumulation is just one piece of the storage puzzle. Let me share some battle-tested techniques beyond the standard recommendations.

While Microsoft warns against manually deleting compressed uninstall directories, we can safely use:

# PowerShell command to analyze patch storage
Get-WindowsUpdateLog -Analyze -EtwLogFile "C:\Windows\WindowsUpdate.log"

Most admins know about clearing temp files, but these often get missed:

• IIS logs (C:\inetpub\logs)
• Windows Error Reporting (C:\ProgramData\Microsoft\Windows\WER)
• Print spooler files (C:\Windows\System32\spool\PRINTERS)

Here's a PowerShell script I run monthly across all servers:

# Automated cleanup script
$cleanupPaths = @(
    "C:\Windows\Temp\*",
    "C:\Windows\SoftwareDistribution\Download\*",
    "C:\Windows\Logs\CBS\*"
)

foreach ($path in $cleanupPaths) {
    Remove-Item -Path $path -Force -Recurse -ErrorAction SilentlyContinue
}

# Compact OS for additional savings
compact /compactos:always

Based on my experience with 200+ servers:

For environments with hundreds of servers:

# DSC configuration for consistent cleanup
Configuration ServerCleanup {
    Node "localhost" {
        Script CleanTempFiles {
            GetScript = { @{} }
            SetScript = {
                Get-ChildItem "C:\Windows\Temp" | Remove-Item -Force -Recurse
            }
            TestScript = { $false }
        }
    }
}

Implement this PowerShell monitoring snippet to alert before space runs low:

# Disk space monitor
$threshold = 15 # Percentage threshold
$disk = Get-WmiObject Win32_LogicalDisk -Filter "DeviceID='C:'"
$freeSpace = ($disk.FreeSpace / $disk.Size) * 100

if ($freeSpace -lt $threshold) {
    Send-MailMessage -To "admin@domain.com" -Subject "Low Disk Space Alert" -Body "C: drive has only $freeSpace% free space remaining"
}