diff --git a/images/macos/provision/core/powershell.sh b/images/macos/provision/core/powershell.sh
index 7e89ded76..834744856 100644
--- a/images/macos/provision/core/powershell.sh
+++ b/images/macos/provision/core/powershell.sh
@@ -1,15 +1,9 @@
 #!/bin/bash -e -o pipefail
 source ~/utils/utils.sh
 
-echo Installing Azure CLI...
-brew_smart_install "azure-cli"
-
 echo Installing PowerShell...
 brew install --cask powershell
 
-# A dummy call of `az` to initialize ~/.azure directory before the modules are installed
-az -v
-
 # Install PowerShell modules
 psModules=$(get_toolset_value '.powershellModules[].name')
 for module in ${psModules[@]}; do
@@ -31,7 +25,4 @@ pwsh -command "& {Import-Module Az}"
 # powershell link was removed in powershell-6.0.0-beta9
 sudo ln -s /usr/local/bin/pwsh /usr/local/bin/powershell
 
-# fix ~/.azure directory permissions
-sudo chown -R ${USER}: $HOME/.azure
-
 invoke_tests "Powershell"
diff --git a/images/macos/tests/BasicTools.Tests.ps1 b/images/macos/tests/BasicTools.Tests.ps1
index 9ff7b1da1..62b73c2b3 100644
--- a/images/macos/tests/BasicTools.Tests.ps1
+++ b/images/macos/tests/BasicTools.Tests.ps1
@@ -1,5 +1,11 @@
 $os = Get-OSVersion
 
+Describe "Azure CLI" {
+    It "Azure CLI" {
+        "az -v" | Should -ReturnZeroExitCode
+    }
+}
+
 Describe "Carthage" {
     It "Carthage" {
         "carthage version" | Should -ReturnZeroExitCode
diff --git a/images/macos/tests/Powershell.Tests.ps1 b/images/macos/tests/Powershell.Tests.ps1
index b92ac6b20..0674b1ef0 100644
--- a/images/macos/tests/Powershell.Tests.ps1
+++ b/images/macos/tests/Powershell.Tests.ps1
@@ -40,10 +40,4 @@ Describe "Powershell" {
             }
         }
     }
-    
-    Context "Azure CLI" {
-        It "Azure CLI" {
-            "az -v" | 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 6d8c98dc0..40be73438 100644
--- a/images/macos/tests/Python.Tests.ps1
+++ b/images/macos/tests/Python.Tests.ps1
@@ -41,4 +41,9 @@ Describe "Python" {
         $python3Path = Split-Path (readlink (which python3))
         $pip3Path | Should -BeExactly $python3Path
     }
+
+    It "2to3 symlink does not point to Python 2" {
+        $2to3path = (Get-ChildItem (Get-Command 2to3).Path).Target
+        $2to3path | Should -Not -BeLike '/Frameworks/Python.framework/Versions/2.*'
+    }
 }
\ 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 8ed724a8e..3f1637c83 100644
--- a/images/macos/toolsets/toolset-10.14.json
+++ b/images/macos/toolsets/toolset-10.14.json
@@ -243,6 +243,7 @@
             "aliyun-cli",
             "ant",
             "aria2",
+            "azure-cli",
             "bats",
             "bazelisk",
             "carthage",
diff --git a/images/macos/toolsets/toolset-10.15.json b/images/macos/toolsets/toolset-10.15.json
index 5a5a60a3c..899f39f78 100644
--- a/images/macos/toolsets/toolset-10.15.json
+++ b/images/macos/toolsets/toolset-10.15.json
@@ -194,6 +194,7 @@
             "aliyun-cli",
             "ant",
             "aria2",
+            "azure-cli",
             "bats",
             "bazelisk",
             "carthage",
diff --git a/images/macos/toolsets/toolset-11.json b/images/macos/toolsets/toolset-11.json
index bd3590bfe..0e5b7a815 100644
--- a/images/macos/toolsets/toolset-11.json
+++ b/images/macos/toolsets/toolset-11.json
@@ -141,6 +141,7 @@
             "aliyun-cli",
             "ant",
             "aria2",
+            "azure-cli",
             "bazelisk",
             "carthage",
             "cmake",