diff --git a/images/win/scripts/Installers/Install-VCRedist.ps1 b/images/win/scripts/Installers/Install-VCRedist.ps1
index 0defd5090..473fed3a2 100644
--- a/images/win/scripts/Installers/Install-VCRedist.ps1
+++ b/images/win/scripts/Installers/Install-VCRedist.ps1
@@ -12,4 +12,6 @@ if (Test-IsWin19) {
     $ArgumentList = ("/install", "/quiet", "/norestart")
     Install-Binary -Url $Vc2010x86URI -Name $Vc2010x86Name -ArgumentList $ArgumentList
     Install-Binary -Url $Vc2010x64URI -Name $Vc2010x64Name -ArgumentList $ArgumentList
-}
\ No newline at end of file
+}
+
+Invoke-PesterTests -TestFile "Tools" -TestName "VCRedist"
diff --git a/images/win/scripts/Tests/Tools.Tests.ps1 b/images/win/scripts/Tests/Tools.Tests.ps1
index c45660e00..3eb532258 100644
--- a/images/win/scripts/Tests/Tools.Tests.ps1
+++ b/images/win/scripts/Tests/Tools.Tests.ps1
@@ -165,6 +165,22 @@ Describe "Vcpkg" {
     }
 }
 
+Describe "VCRedist" -Skip:(Test-IsWin22) {
+    It "vcredist_140" -Skip:(Test-IsWin19) {
+        "C:\Windows\System32\vcruntime140.dll" | Should -Exist
+    }
+
+    It "vcredist_2010_x64" -Skip:(Test-IsWin16) {
+        "HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\Uninstall\{1D8E6291-B0D5-35EC-8441-6616F567A0F7}" | Should -Exist
+        "C:\Windows\System32\msvcr100.dll" | Should -Exist
+    }
+
+    It "vcredist_2010_x64" -Skip:(Test-IsWin16) {
+        "HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\Uninstall\{1D8E6291-B0D5-35EC-8441-6616F567A0F7}" | Should -Exist
+        "C:\Windows\System32\msvcr100.dll" | Should -Exist
+    }
+}
+
 Describe "WebPlatformInstaller" -Skip:(Test-IsWin22) {
     It "WebPlatformInstaller" {
         "WebPICMD" | Should -ReturnZeroExitCode
diff --git a/images/win/windows2019.json b/images/win/windows2019.json
index af3c1ea91..fe47fea33 100644
--- a/images/win/windows2019.json
+++ b/images/win/windows2019.json
@@ -143,6 +143,8 @@
         },
         {
             "type": "windows-restart",
+            "check_registry": true,
+            "restart_check_command": "powershell -command \"& {if (-not (Get-Process TiWorker.exe -ErrorAction SilentlyContinue)) { Write-Output 'Restart complete' }}\"",
             "restart_timeout": "30m"
         },
         {
diff --git a/images/win/windows2022.json b/images/win/windows2022.json
index 2c92c3923..d35c0c637 100644
--- a/images/win/windows2022.json
+++ b/images/win/windows2022.json
@@ -144,7 +144,6 @@
         {
             "type": "powershell",
             "scripts": [
-                "{{ template_dir }}/scripts/Installers/Install-VCRedist.ps1",
                 "{{ template_dir }}/scripts/Installers/Install-Docker.ps1",
                 "{{ template_dir }}/scripts/Installers/Install-PowershellCore.ps1"
             ]