diff --git a/images/win/Windows2016-Azure.json b/images/win/Windows2016-Azure.json
index a29928b86..3c12ab023 100644
--- a/images/win/Windows2016-Azure.json
+++ b/images/win/Windows2016-Azure.json
@@ -124,7 +124,8 @@
             ],
             "scripts":[
                 "{{ template_dir }}/scripts/Installers/Install-PowerShellModules.ps1",
-                "{{ template_dir }}/scripts/Installers/Initialize-VM.ps1"
+                "{{ template_dir }}/scripts/Installers/Initialize-VM.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-WebPlatformInstaller.ps1"
             ],
             "execution_policy": "unrestricted"
         },
diff --git a/images/win/Windows2019-Azure.json b/images/win/Windows2019-Azure.json
index 44059d360..c0bee9873 100644
--- a/images/win/Windows2019-Azure.json
+++ b/images/win/Windows2019-Azure.json
@@ -124,7 +124,8 @@
             ],
             "scripts":[
                 "{{ template_dir }}/scripts/Installers/Install-PowerShellModules.ps1",
-                "{{ template_dir }}/scripts/Installers/Initialize-VM.ps1"
+                "{{ template_dir }}/scripts/Installers/Initialize-VM.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-WebPlatformInstaller.ps1"
             ],
             "execution_policy": "unrestricted"
         },
diff --git a/images/win/scripts/Installers/Initialize-VM.ps1 b/images/win/scripts/Installers/Initialize-VM.ps1
index 27efea2b5..550eb8a34 100644
--- a/images/win/scripts/Installers/Initialize-VM.ps1
+++ b/images/win/scripts/Installers/Initialize-VM.ps1
@@ -114,9 +114,6 @@ choco feature enable -n allowGlobalConfirmation
 # Remove some of the command aliases, like `cpack` #89
 Remove-Item -Path $env:ChocolateyInstall\bin\cpack.exe -Force
 
-# Install webpi
-Choco-Install -PackageName webpicmd
-
 if (Test-IsWin16) {
     # Install vcredist140
     Choco-Install -PackageName vcredist140
diff --git a/images/win/scripts/Installers/Install-WebPlatformInstaller.ps1 b/images/win/scripts/Installers/Install-WebPlatformInstaller.ps1
new file mode 100644
index 000000000..2263b3a9a
--- /dev/null
+++ b/images/win/scripts/Installers/Install-WebPlatformInstaller.ps1
@@ -0,0 +1,11 @@
+################################################################################
+##  File:  Install-WebPI.ps1
+##  Desc:  Install WebPlatformInstaller
+################################################################################
+
+# Download and install WebPlatformInstaller
+$webPlatformInstallerFile = "WebPlatformInstaller_x64_en-US.msi"
+$webPlatformInstallerUrl = "http://go.microsoft.com/fwlink/?LinkId=287166"
+Install-Binary -Url $webPlatformInstallerUrl -Name $webPlatformInstallerFile -ArgumentList ("/silent", "/install")
+
+Invoke-PesterTests -TestFile "Tools" -TestName "WebPlatformInstaller"
\ No newline at end of file
diff --git a/images/win/scripts/Tests/Tools.Tests.ps1 b/images/win/scripts/Tests/Tools.Tests.ps1
index 22d17b7e2..88f2ca88f 100644
--- a/images/win/scripts/Tests/Tools.Tests.ps1
+++ b/images/win/scripts/Tests/Tools.Tests.ps1
@@ -243,6 +243,12 @@ Describe "VSWhere" {
     }
 }
 
+Describe "WebPlatformInstaller" {
+    It "WebPlatformInstaller" {
+        "WebPICMD" | Should -ReturnZeroExitCode
+    }
+}
+
 Describe "Zstd" {
     It "zstd" {
         "zstd -V" | Should -ReturnZeroExitCode