diff --git a/images/win/scripts/Installers/Install-Pipx.ps1 b/images/win/scripts/Installers/Install-Pipx.ps1
new file mode 100644
index 00000000..a78cf456
--- /dev/null
+++ b/images/win/scripts/Installers/Install-Pipx.ps1
@@ -0,0 +1,14 @@
+#   Set custom directorys for pipx
+$env:PIPX_BIN_DIR = "${env:ProgramFiles(x86)}\pipx_bin"
+$env:PIPX_HOME = "${env:ProgramFiles(x86)}\pipx"
+
+#   Install pipx
+pip install pipx
+
+#   Set environment variables
+Add-MachinePathItem "${env:PIPX_BIN_DIR}"
+Set-SystemVariable -SystemVariable PIPX_BIN_DIR -Value $env:PIPX_BIN_DIR
+Set-SystemVariable -SystemVariable PIPX_HOME -Value $env:PIPX_HOME
+
+#   Test pipx
+Invoke-PesterTests -TestFile "Tools" -TestName "Pipx"
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-PipxPackages.ps1 b/images/win/scripts/Installers/Install-PipxPackages.ps1
new file mode 100644
index 00000000..e83f5add
--- /dev/null
+++ b/images/win/scripts/Installers/Install-PipxPackages.ps1
@@ -0,0 +1,12 @@
+$pipxToolset = (Get-ToolsetContent).pipx
+foreach($tool in $pipxToolset) {
+    if ($tool.python) {
+        $pythonPath = (Get-Item  -Path "${env:AGENT_TOOLSDIRECTORY}\Python\${tool.python}.*\x64\python-${tool.python}*").FullName
+        Write-Host "Install ${tool.package} into python ${tool.python}"
+        pipx install $tool.package --python $pythonPath
+    } else {
+        Write-Host "Install ${tool.package} into default python"
+        pipx install $tool.package
+    }
+}
+Invoke-PesterTests -TestFile "PipxPackages"
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-YAMLLint.ps1 b/images/win/scripts/Installers/Install-YAMLLint.ps1
deleted file mode 100644
index 1ebc09a3..00000000
--- a/images/win/scripts/Installers/Install-YAMLLint.ps1
+++ /dev/null
@@ -1,3 +0,0 @@
-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 ea56e1ff..72a33619 100644
--- a/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1
+++ b/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1
@@ -292,3 +292,8 @@ function Get-ShellTarget {
 function Get-YAMLLintVersion {
     yamllint --version
 }
+
+function Get-PipxVersion {
+    $pipxVersion = pipx --version
+    return "Pipx $pipxVersion"
+}
diff --git a/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1 b/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
index aba000b7..fff45919 100644
--- a/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
+++ b/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
@@ -59,7 +59,8 @@ $markdown += New-MDList -Style Unordered -Lines @(
     (Get-RubyGemsVersion),
     (Get-HelmVersion),
     (Get-ComposerVersion),
-    (Get-NugetVersion)
+    (Get-NugetVersion),
+    (Get-PipxVersion)
 )
 
 $markdown += New-MDHeader "Project Management" -Level 3
diff --git a/images/win/scripts/Tests/PipxPackages.Tests.ps1 b/images/win/scripts/Tests/PipxPackages.Tests.ps1
new file mode 100644
index 00000000..41041078
--- /dev/null
+++ b/images/win/scripts/Tests/PipxPackages.Tests.ps1
@@ -0,0 +1,7 @@
+Describe "PipxPackages" {
+    $pipxToolset = (Get-ToolsetContent).pipx
+    $testCases = $pipxToolset | ForEach-Object { @{package = $_.package; cmd = $_.cmd} }
+    It "<package>" -TestCases $testCases {
+        "$cmd" | Should -ReturnZeroExitCode
+    }
+}
\ 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 cbb0609a..a0024532 100644
--- a/images/win/scripts/Tests/Tools.Tests.ps1
+++ b/images/win/scripts/Tests/Tools.Tests.ps1
@@ -214,12 +214,6 @@ Describe "ServiceFabricSDK" {
     }
 }
 
-Describe "yamllint" {
-    It "yamllint" {
-        "yamllint --version" | Should -ReturnZeroExitCode
-    }
-}
-
 Describe "Svn" {
     It "svn" {
         "svn --version --quiet" | Should -ReturnZeroExitCode
@@ -269,3 +263,9 @@ Describe "Zstd" {
         "zstd -V" | Should -ReturnZeroExitCode
     }
 }
+
+Describe "Pipx" {
+    It "Pipx" {
+        "pipx --version" | Should -ReturnZeroExitCode
+    }
+}
diff --git a/images/win/toolsets/toolset-2016.json b/images/win/toolsets/toolset-2016.json
index 8b6f32f3..f5d30694 100644
--- a/images/win/toolsets/toolset-2016.json
+++ b/images/win/toolsets/toolset-2016.json
@@ -237,5 +237,11 @@
             "mcr.microsoft.com/dotnet/framework/runtime:4.8-windowsservercore-ltsc2016",
             "microsoft/aspnetcore-build:1.0-2.0"
         ]
-    }
+    },
+    "pipx": [
+        {
+            "package": "yamllint",
+            "cmd": "yamllint --version"
+        }
+    ]
 }
diff --git a/images/win/toolsets/toolset-2019.json b/images/win/toolsets/toolset-2019.json
index a056fd88..ebb7aa82 100644
--- a/images/win/toolsets/toolset-2019.json
+++ b/images/win/toolsets/toolset-2019.json
@@ -280,5 +280,11 @@
             "mcr.microsoft.com/dotnet/framework/runtime:4.8-windowsservercore-ltsc2019",
             "microsoft/aspnetcore-build:1.0-2.0"
         ]
-    }
+    },
+    "pipx": [
+        {
+            "package": "yamllint",
+            "cmd": "yamllint --version"
+        }
+    ]
 }
diff --git a/images/win/windows2016.json b/images/win/windows2016.json
index 8c1314d6..8136ebd4 100644
--- a/images/win/windows2016.json
+++ b/images/win/windows2016.json
@@ -235,8 +235,9 @@
                 "{{ 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/Install-YAMLLint.ps1",
-                "{{ template_dir }}/scripts/Installers/Update-AndroidSDK.ps1"
+                "{{ template_dir }}/scripts/Installers/Update-AndroidSDK.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-Pipx.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-PipxPackages.ps1"
             ]
         },
         {
diff --git a/images/win/windows2019.json b/images/win/windows2019.json
index a002f77f..f20e050c 100644
--- a/images/win/windows2019.json
+++ b/images/win/windows2019.json
@@ -249,9 +249,10 @@
                 "{{ 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/Install-YAMLLint.ps1",
                 "{{ template_dir }}/scripts/Installers/Update-AndroidSDK.ps1",
-                "{{ template_dir }}/scripts/Installers/Install-AzureModules.ps1"
+                "{{ template_dir }}/scripts/Installers/Install-AzureModules.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-Pipx.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-PipxPackages.ps1"
             ]
         },
         {