diff --git a/images/macos/provision/core/commonutils.sh b/images/macos/provision/core/commonutils.sh
index 9b32d5c2..5b3522f5 100644
--- a/images/macos/provision/core/commonutils.sh
+++ b/images/macos/provision/core/commonutils.sh
@@ -22,7 +22,6 @@ binst_common_utils=(
     github/gh/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..c01a4b97
--- /dev/null
+++ b/images/macos/provision/core/pipx-packages.sh
@@ -0,0 +1,25 @@
+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="/opt/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 $package
+    fi
+
+    # Run tests to determine that the software installed as expected
+    cmd=$(jq -r ".pipx[] | select(.package == \"$package\") .cmd" $toolset)
+    if ! command -v $cmd; then
+        echo "$package was not installed"
+        exit 1
+    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 41488642..5bda9ef3 100755
--- a/images/macos/provision/core/python.sh
+++ b/images/macos/provision/core/python.sh
@@ -7,7 +7,19 @@ echo "Brew Installing Python 3"
 /usr/local/bin/brew install python3
 
 echo "Brew Installing Python 2"
-# Create local tap with formula due to python2 formula depreciation 
+# Create local tap with formula due to python2 formula depreciation
 /usr/local/bin/brew tap-new local/python2
 FORMULA_PATH=$(/usr/local/bin/brew extract python@2 local/python2 | grep "Homebrew/Library/Taps")
 /usr/local/bin/brew install $FORMULA_PATH
+
+echo "Installing pipx"
+export PIPX_BIN_DIR=/opt/pipx_bin
+export PIPX_HOME=/opt/pipx
+
+brew install pipx
+python3 -m pipx ensurepath
+
+echo "export PIPX_BIN_DIR=${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..5c518d16 100644
--- a/images/macos/software-report/SoftwareReport.Common.psm1
+++ b/images/macos/software-report/SoftwareReport.Common.psm1
@@ -96,6 +96,10 @@ function Get-PipVersion {
     return "${versionPart1} ${versionPart2} ${versionPart3}"
 }
 
+function Get-PipxVersion {
+    return "Pipx $(pipx --version 2> $null)"
+}
+
 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 87c94459..40214d7a 100644
--- a/images/macos/software-report/SoftwareReport.Generator.ps1
+++ b/images/macos/software-report/SoftwareReport.Generator.ps1
@@ -81,6 +81,7 @@ $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"
 $composerVersion = Run-Command "composer --version" | Take-Part -Part 2
@@ -97,6 +98,7 @@ if ($os.IsLessThanBigSur) {
 
 $markdown += New-MDList -Style Unordered -Lines @(
     "Pip ${pip3Version}",
+    $pipxVersion,
     $bundlerVersion,
     "Carthage ${carthageVersion}",
     "CocoaPods ${cocoaPodsVersion}",
diff --git a/images/macos/templates/macOS-10.14.json b/images/macos/templates/macOS-10.14.json
index 269ffa71..3cb0b070 100644
--- a/images/macos/templates/macOS-10.14.json
+++ b/images/macos/templates/macOS-10.14.json
@@ -196,6 +196,13 @@
             "execute_command": "chmod +x {{ .Path }}; {{ .Vars }} pwsh -f {{ .Path }}",
             "scripts": "./provision/core/toolset.ps1"
         },
+        {
+            "type": "shell",
+            "execute_command": "chmod +x {{ .Path }}; {{ .Vars }} {{ .Path }}",
+            "scripts": [
+                "./provision/core/pipx-packages.sh"
+            ]
+        },
         {
             "type": "shell",
             "execute_command": "ruby {{ .Path }}",
diff --git a/images/macos/templates/macOS-10.15.json b/images/macos/templates/macOS-10.15.json
index 3dcc3d33..65a0d12d 100644
--- a/images/macos/templates/macOS-10.15.json
+++ b/images/macos/templates/macOS-10.15.json
@@ -195,6 +195,13 @@
             "execute_command": "chmod +x {{ .Path }}; {{ .Vars }} pwsh -f {{ .Path }}",
             "scripts": "./provision/core/toolset.ps1"
         },
+        {
+            "type": "shell",
+            "execute_command": "chmod +x {{ .Path }}; {{ .Vars }} {{ .Path }}",
+            "scripts": [
+                "./provision/core/pipx-packages.sh"
+            ]
+        },
         {
             "type": "shell",
             "execute_command": "ruby {{ .Path }}",
diff --git a/images/macos/templates/macOS-11.0.json b/images/macos/templates/macOS-11.0.json
index 6da9df38..c732f799 100644
--- a/images/macos/templates/macOS-11.0.json
+++ b/images/macos/templates/macOS-11.0.json
@@ -192,6 +192,13 @@
             "execute_command": "chmod +x {{ .Path }}; {{ .Vars }} pwsh -f {{ .Path }}",
             "scripts": "./provision/core/toolset.ps1"
         },
+        {
+            "type": "shell",
+            "execute_command": "chmod +x {{ .Path }}; {{ .Vars }} {{ .Path }}",
+            "scripts": [
+                "./provision/core/pipx-packages.sh"
+            ]
+        },
         {
             "type": "shell",
             "execute_command": "ruby {{ .Path }}",
diff --git a/images/macos/toolsets/toolset-10.14.json b/images/macos/toolsets/toolset-10.14.json
index e868f769..fc1d44af 100644
--- a/images/macos/toolsets/toolset-10.14.json
+++ b/images/macos/toolsets/toolset-10.14.json
@@ -257,5 +257,11 @@
                 "1.15.*"
             ]
         }
+    ],
+    "pipx": [
+        {
+            "package": "yamllint",
+            "cmd": "yamllint"
+        }
     ]
 }
\ 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 8497a710..e754bacf 100644
--- a/images/macos/toolsets/toolset-10.15.json
+++ b/images/macos/toolsets/toolset-10.15.json
@@ -26,28 +26,28 @@
                 "mono":"6.12",
                 "ios": "14.0",
                 "mac": "6.20",
-                "android": "11.0" 
+                "android": "11.0"
             },
             {
                 "symlink": "6_12_0",
                 "mono":"6.12",
                 "ios": "13.20",
                 "mac": "6.20",
-                "android": "11.0" 
+                "android": "11.0"
             },
             {
                 "symlink": "6_10_0",
                 "mono":"6.10",
                 "ios": "13.18",
                 "mac": "6.18",
-                "android": "10.3" 
+                "android": "10.3"
             },
             {
                 "symlink": "6_8_1",
                 "mono":"6.8",
                 "ios": "13.16",
                 "mac": "6.16",
-                "android": "10.2" 
+                "android": "10.2"
             },
             {
                 "symlink": "6_8_0",
@@ -166,5 +166,11 @@
                 "1.15.*"
             ]
         }
+    ],
+    "pipx": [
+        {
+            "package": "yamllint",
+            "cmd": "yamllint"
+        }
     ]
 }
\ 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 725da218..8a739f91 100644
--- a/images/macos/toolsets/toolset-11.0.json
+++ b/images/macos/toolsets/toolset-11.0.json
@@ -26,14 +26,14 @@
                 "mono":"6.12",
                 "ios": "14.0",
                 "mac": "6.20",
-                "android": "11.0" 
+                "android": "11.0"
             },
             {
                 "symlink": "6_12_0",
                 "mono":"6.12",
                 "ios": "13.20",
                 "mac": "6.20",
-                "android": "11.0" 
+                "android": "11.0"
             }
         ]
     },
@@ -91,5 +91,11 @@
                 "1.15.*"
             ]
         }
+    ],
+    "pipx": [
+        {
+            "package": "yamllint",
+            "cmd": "yamllint"
+        }
     ]
 }
\ No newline at end of file