diff --git a/.expeditor/buildkite/artifact.habitat.test.ps1 b/.expeditor/buildkite/artifact.habitat.test.ps1
index b97c50c13..702873e9c 100755
--- a/.expeditor/buildkite/artifact.habitat.test.ps1
+++ b/.expeditor/buildkite/artifact.habitat.test.ps1
@@ -15,12 +15,41 @@ $Properties = 'Caption', 'CSName', 'Version', 'BuildType', 'OSArchitecture'
 Get-CimInstance Win32_OperatingSystem | Select-Object $Properties | Format-Table -AutoSize
 
 Write-Host "--- Installing the version of Habitat required"
+
+function Stop-HabProcess {
+  $habProcess = Get-Process hab -ErrorAction SilentlyContinue
+  if ($habProcess) {
+      Write-Host "Stopping hab process..."
+      Stop-Process -Name hab -Force
+  }
+}
+
+function Install-Habitat {
+  Write-Host "Downloading and installing Habitat..."
+  Invoke-Expression ((New-Object System.Net.WebClient).DownloadString('https://raw.githubusercontent.com/habitat-sh/habitat/main/components/hab/install.ps1'))
+}
+
 try {
   hab --version
 }
 catch {
   Set-ExecutionPolicy Bypass -Scope Process -Force
-  Invoke-Expression ((New-Object System.Net.WebClient).DownloadString('https://raw.githubusercontent.com/habitat-sh/habitat/main/components/hab/install.ps1'))
+
+  Stop-HabProcess
+
+  # Remove the existing hab.exe if it exists and if you have permissions
+  $habPath = "C:\ProgramData\Habitat\hab.exe"
+  if (Test-Path $habPath) {
+      Write-Host "Attempting to remove existing hab.exe..."
+      Remove-Item $habPath -Force -ErrorAction SilentlyContinue
+      if (Test-Path $habPath) {
+          Write-Host "Failed to remove hab.exe, re-running script with elevated permissions."
+          Start-Process powershell -Verb runAs -ArgumentList "-NoProfile -ExecutionPolicy Bypass -File `"$PSCommandPath`""
+          exit
+      }
+  }
+
+  Install-Habitat
 }
 finally {
   Write-Host ":habicat: I think I have the version I need to build."