diff --git a/images/win/Windows2016-Azure.json b/images/win/Windows2016-Azure.json
index 08429f3c8..0e1fabbf3 100644
--- a/images/win/Windows2016-Azure.json
+++ b/images/win/Windows2016-Azure.json
@@ -339,7 +339,8 @@
             "scripts":[
                 "{{ template_dir }}/scripts/Installers/Install-PyPy.ps1",
                 "{{ template_dir }}/scripts/Installers/Install-Toolset.ps1",
-                "{{ template_dir }}/scripts/Installers/Configure-Toolset.ps1"
+                "{{ template_dir }}/scripts/Installers/Configure-Toolset.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-YAMLLint.ps1"
             ]
         },
         {
diff --git a/images/win/Windows2019-Azure.json b/images/win/Windows2019-Azure.json
index fd25e63a7..137b52562 100644
--- a/images/win/Windows2019-Azure.json
+++ b/images/win/Windows2019-Azure.json
@@ -314,7 +314,8 @@
             "scripts":[
                 "{{ template_dir }}/scripts/Installers/Install-PyPy.ps1",
                 "{{ template_dir }}/scripts/Installers/Install-Toolset.ps1",
-                "{{ template_dir }}/scripts/Installers/Configure-Toolset.ps1"
+                "{{ template_dir }}/scripts/Installers/Configure-Toolset.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-YAMLLint.ps1"
             ]
         },
         {
diff --git a/images/win/scripts/Installers/Install-YAMLLint.ps1 b/images/win/scripts/Installers/Install-YAMLLint.ps1
new file mode 100644
index 000000000..1ebc09a33
--- /dev/null
+++ b/images/win/scripts/Installers/Install-YAMLLint.ps1
@@ -0,0 +1,3 @@
+pip install yamllint
+
+Invoke-PesterTests -TestFile "Tools" -TestName "yamllint"
\ No newline at end of file
diff --git a/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1 b/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1
index 965b5fb93..05b101aac 100644
--- a/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1
+++ b/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1
@@ -270,3 +270,7 @@ function Get-PacmanVersion {
     $pacmanVersion = $matches[0]
     return "- Pacman $pacmanVersion"
 }
+
+function Get-YAMLLintVersion {
+    yamllint --version
+}
\ No newline at end of file
diff --git a/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1 b/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
index 49f15be6f..a9968f8c0 100644
--- a/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
+++ b/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
@@ -98,7 +98,8 @@ $markdown += New-MDList -Style Unordered -Lines @(
     (Get-WinAppDriver),
     (Get-ZstdVersion),
     (Get-VSWhereVersion),
-    (Get-7zipVersion)
+    (Get-7zipVersion),
+    (Get-YAMLLintVersion)
 )
 
 $markdown += New-MDHeader "CLI Tools" -Level 3
diff --git a/images/win/scripts/Tests/Tools.Tests.ps1 b/images/win/scripts/Tests/Tools.Tests.ps1
index 12278e43b..fe3343cf7 100644
--- a/images/win/scripts/Tests/Tools.Tests.ps1
+++ b/images/win/scripts/Tests/Tools.Tests.ps1
@@ -247,6 +247,12 @@ Describe "ServiceFabricSDK" {
     }
 }
 
+Describe "yamllint" {
+    It "yamllint" {
+        "yamllint --version" | Should -ReturnZeroExitCode
+    }
+}
+
 Describe "Svn" {
     It "svn" {
         "svn --version --quiet" | Should -ReturnZeroExitCode