diff --git a/Cleanup-SystemTempFiles.ps1 b/Cleanup-SystemTempFiles.ps1
index 1ba0921..9d8a12c 100644
--- a/Cleanup-SystemTempFiles.ps1
+++ b/Cleanup-SystemTempFiles.ps1
@@ -117,12 +117,16 @@ If ( Test-Path $ADSKInst ) {
     }
 }
 
-# Delete the oldest shadow copies if there are more than 1
+# Delete all but most recent shadow copy of system drive
 $SystemVolume = Get-CimInstance -ClassName Win32_Volume -ErrorAction SilentlyContinue | Where-Object { $_.Name -like "${Env:SystemDrive}\" }
 $ShadowCopies = Get-CimInstance -ClassName Win32_ShadowCopy | Where-Object { $_.VolumeName -like $SystemVolume.DeviceID }
 If ( $ShadowCopies.Length -gt 1 ) {
-    Write-Output "Deleting oldest shadow copy on ${Env:SystemDrive}"
-    vssadmin delete shadows /For=$Env:SystemDrive /Oldest /Quiet
+    Write-Output "Deleting all of the oldest shadow copies on ${Env:SystemDrive}"
+    $ShadowsToDelete = $ShadowCopies.Length - 1
+    While ( $ShadowsToDelete -gt 0 ) {
+        $ShadowsToDelete = $ShadowsToDelete - 1
+        vssadmin delete shadows /For=$Env:SystemDrive /Oldest /Quiet
+    }   
 }
 
 # Remove files from user profile directories