diff --git a/images/macos/provision/core/commonutils.sh b/images/macos/provision/core/commonutils.sh
index c7e93496..a479974c 100644
--- a/images/macos/provision/core/commonutils.sh
+++ b/images/macos/provision/core/commonutils.sh
@@ -21,7 +21,6 @@ binst_common_utils=(
     gh
     p7zip
     ant
-    yamllint
     aria2
 )
 
diff --git a/images/macos/provision/core/pipx-packages.sh b/images/macos/provision/core/pipx-packages.sh
new file mode 100644
index 00000000..658600fa
--- /dev/null
+++ b/images/macos/provision/core/pipx-packages.sh
@@ -0,0 +1,18 @@
+source ~/utils/utils.sh
+
+export PATH="$PATH:/opt/pipx_bin"
+
+toolset=$(get_toolset_path)
+pipx_packages=$(jq -r ".pipx[] .package" $toolset)
+
+for package in $pipx_packages; do
+    python_version=$(jq -r ".pipx[] | select(.package == \"$package\") .python" $toolset)
+    if [ "$python_version" != "null" ]; then
+        python_path="$HOME/hostedtoolcache/Python/$python_version*/x64/bin/python$python_version"
+        echo "Install $package into python $python_path"
+        pipx install $package --python $python_path
+    else
+        echo "Install $package into default python"
+        pipx install $package
+    fi
+done
\ No newline at end of file
diff --git a/images/macos/provision/core/python.sh b/images/macos/provision/core/python.sh
index b4c64147..62922053 100755
--- a/images/macos/provision/core/python.sh
+++ b/images/macos/provision/core/python.sh
@@ -17,3 +17,13 @@ echo "Brew Installing Python 2"
 brew tap-new --no-git local/python2
 FORMULA_PATH=$(brew extract python@2 local/python2 | grep "Homebrew/Library/Taps")
 brew install $FORMULA_PATH
+
+echo "Installing pipx"
+export PIPX_BIN_DIR=/usr/local/opt/pipx_bin
+export PIPX_HOME=/usr/local/opt/pipx
+
+brew install pipx
+
+echo "export PIPX_BIN_DIR=${PIPX_BIN_DIR}" >> "${HOME}/.bashrc"
+echo "export PIPX_HOME=${PIPX_HOME}" >> "${HOME}/.bashrc"
+echo 'export PATH="$PIPX_BIN_DIR:$PATH"' >> "${HOME}/.bashrc"
diff --git a/images/macos/software-report/SoftwareReport.Common.psm1 b/images/macos/software-report/SoftwareReport.Common.psm1
index c3fe7517..7616b81b 100644
--- a/images/macos/software-report/SoftwareReport.Common.psm1
+++ b/images/macos/software-report/SoftwareReport.Common.psm1
@@ -96,6 +96,11 @@ function Get-PipVersion {
     return "${versionPart1} ${versionPart2} ${versionPart3}"
 }
 
+function Get-PipxVersion {
+    $pipxVersion = Run-Command "pipx --version" -SuppressStderr
+    return "Pipx $pipxVersion"
+}
+
 function Get-NVMNodeVersionList {
     $nvmPath = Join-Path $env:HOME ".nvm" "nvm.sh"
     $nvmInitCommand = ". ${nvmPath} > /dev/null 2>&1 || true"
diff --git a/images/macos/software-report/SoftwareReport.Generator.ps1 b/images/macos/software-report/SoftwareReport.Generator.ps1
index 9bcef14c..4eab767c 100644
--- a/images/macos/software-report/SoftwareReport.Generator.ps1
+++ b/images/macos/software-report/SoftwareReport.Generator.ps1
@@ -83,6 +83,7 @@ $npmVersion = Run-Command "npm --version"
 $yarnVersion = Run-Command "yarn --version"
 $nugetVersion = Run-Command "nuget help" | Select-Object -First 1 | Take-Part -Part 2
 $pip3Version = Get-PipVersion -Version 3
+$pipxVersion = Get-PipxVersion
 $condaVersion = Invoke-Expression "conda --version"
 $rubyGemsVersion = Run-Command "gem --version"
 $composerVersion = Run-Command "composer --version" | Take-Part -Part 2
@@ -99,6 +100,7 @@ if ($os.IsLessThanBigSur) {
 
 $markdown += New-MDList -Style Unordered -Lines @(
     "Pip ${pip3Version}",
+    $pipxVersion,
     $bundlerVersion,
     "Carthage ${carthageVersion}",
     "CocoaPods ${cocoaPodsVersion}",
diff --git a/images/macos/templates/macOS-10.13.json b/images/macos/templates/macOS-10.13.json
index 35c7ef3c..9ebd56e6 100644
--- a/images/macos/templates/macOS-10.13.json
+++ b/images/macos/templates/macOS-10.13.json
@@ -181,7 +181,8 @@
                 "./provision/core/edge.sh",
                 "./provision/core/firefox.sh",
                 "./provision/core/toolcache-high-sierra.sh",
-                "./provision/core/pypy.sh"
+                "./provision/core/pypy.sh",
+                "./provision/core/pipx-packages.sh"
             ]
         },
         {
diff --git a/images/macos/templates/macOS-10.14.json b/images/macos/templates/macOS-10.14.json
index 2687302e..c03cc72a 100644
--- a/images/macos/templates/macOS-10.14.json
+++ b/images/macos/templates/macOS-10.14.json
@@ -186,7 +186,8 @@
                 "./provision/core/miniconda.sh",
                 "./provision/core/xcode-postbuild.sh",
                 "./provision/core/toolcache.sh",
-                "./provision/core/pypy.sh"
+                "./provision/core/pypy.sh",
+                "./provision/core/pipx-packages.sh"
             ],
             "environment_vars": [
                 "GITHUB_FEED_TOKEN={{user `github_feed_token`}}"
diff --git a/images/macos/templates/macOS-10.15.json b/images/macos/templates/macOS-10.15.json
index a65bd72a..cf49ef57 100644
--- a/images/macos/templates/macOS-10.15.json
+++ b/images/macos/templates/macOS-10.15.json
@@ -185,7 +185,8 @@
                 "./provision/core/firefox.sh",
                 "./provision/core/xcode-postbuild.sh",
                 "./provision/core/toolcache.sh",
-                "./provision/core/pypy.sh"
+                "./provision/core/pypy.sh",
+                "./provision/core/pipx-packages.sh"
             ],
             "environment_vars": [
                 "GITHUB_FEED_TOKEN={{user `github_feed_token`}}"
diff --git a/images/macos/templates/macOS-11.0.json b/images/macos/templates/macOS-11.0.json
index 27f39bfb..585a9354 100644
--- a/images/macos/templates/macOS-11.0.json
+++ b/images/macos/templates/macOS-11.0.json
@@ -181,7 +181,8 @@
                 "./provision/core/chrome.sh",
                 "./provision/core/edge.sh",
                 "./provision/core/firefox.sh",
-                "./provision/core/toolcache.sh"
+                "./provision/core/toolcache.sh",
+                "./provision/core/pipx-packages.sh"
             ],
             "environment_vars": [
                 "GITHUB_FEED_TOKEN={{user `github_feed_token`}}"
diff --git a/images/macos/tests/Linters.Tests.ps1 b/images/macos/tests/Linters.Tests.ps1
index 3b7b8e0d..31d3698c 100644
--- a/images/macos/tests/Linters.Tests.ps1
+++ b/images/macos/tests/Linters.Tests.ps1
@@ -3,10 +3,6 @@ Import-Module "$PSScriptRoot/../helpers/Tests.Helpers.psm1"
 $os = Get-OSVersion
 
 Describe "Linters" {
-    It "yamllint" {
-        "yamllint --version" | Should -ReturnZeroExitCode
-    }
-
     It "SwiftLint" -Skip:($os.IsHighSierra) {
         "swiftlint version" | Should -ReturnZeroExitCode
     }
diff --git a/images/macos/tests/PipxPackages.Tests.ps1 b/images/macos/tests/PipxPackages.Tests.ps1
new file mode 100644
index 00000000..ed981938
--- /dev/null
+++ b/images/macos/tests/PipxPackages.Tests.ps1
@@ -0,0 +1,7 @@
+Describe "PipxPackages" {
+    $pipxToolset = Get-ToolsetValue "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/macos/tests/Python.Tests.ps1 b/images/macos/tests/Python.Tests.ps1
index 62460999..7a50a7ab 100644
--- a/images/macos/tests/Python.Tests.ps1
+++ b/images/macos/tests/Python.Tests.ps1
@@ -32,6 +32,10 @@ Describe "Python" {
         "pip3 --version" | Should -ReturnZeroExitCode
     }
 
+    It "Pipx is available" {
+        "pipx --version" | Should -ReturnZeroExitCode
+    }
+
     It "Pip 3 and Python 3 came from the same brew formula" {
         $pip3Path = Split-Path (readlink (which pip3))
         $python3Path = Split-Path (readlink (which python3))
diff --git a/images/macos/toolsets/toolset-10.13.json b/images/macos/toolsets/toolset-10.13.json
index 6c12251b..3bf62968 100644
--- a/images/macos/toolsets/toolset-10.13.json
+++ b/images/macos/toolsets/toolset-10.13.json
@@ -194,5 +194,11 @@
                 "3.6"
             ]
         }
+    ],
+    "pipx": [
+        {
+            "package": "yamllint",
+            "cmd": "yamllint --version"
+        }
     ]
 }
\ No newline at end of file
diff --git a/images/macos/toolsets/toolset-10.14.json b/images/macos/toolsets/toolset-10.14.json
index 2abe9803..aa1b4101 100644
--- a/images/macos/toolsets/toolset-10.14.json
+++ b/images/macos/toolsets/toolset-10.14.json
@@ -254,5 +254,11 @@
                 "1.15.*"
             ]
         }
+    ],
+    "pipx": [
+        {
+            "package": "yamllint",
+            "cmd": "yamllint --version"
+        }
     ]
 }
\ No newline at end of file
diff --git a/images/macos/toolsets/toolset-10.15.json b/images/macos/toolsets/toolset-10.15.json
index fc0bf798..e041c15e 100644
--- a/images/macos/toolsets/toolset-10.15.json
+++ b/images/macos/toolsets/toolset-10.15.json
@@ -163,5 +163,11 @@
                 "1.15.*"
             ]
         }
+    ],
+    "pipx": [
+        {
+            "package": "yamllint",
+            "cmd": "yamllint --version"
+        }
     ]
 }
\ No newline at end of file
diff --git a/images/macos/toolsets/toolset-11.0.json b/images/macos/toolsets/toolset-11.0.json
index 5ff2280a..cb14b3a0 100644
--- a/images/macos/toolsets/toolset-11.0.json
+++ b/images/macos/toolsets/toolset-11.0.json
@@ -88,5 +88,11 @@
                 "1.15.*"
             ]
         }
+    ],
+    "pipx": [
+        {
+            "package": "yamllint",
+            "cmd": "yamllint --version"
+        }
     ]
 }
\ No newline at end of file