diff --git a/images/macos/provision/core/python.sh b/images/macos/provision/core/python.sh
index 287070b1b..be801340b 100755
--- a/images/macos/provision/core/python.sh
+++ b/images/macos/provision/core/python.sh
@@ -7,7 +7,18 @@ if is_Monterey || is_BigSur; then
     echo "Install latest Python 2"
     Python2Url="https://www.python.org/ftp/python/2.7.18/python-2.7.18-macosx10.9.pkg"
     download_with_retries $Python2Url "/tmp" "python2.pkg"
-    sudo installer -pkg /tmp/python2.pkg -target /
+
+    sudo installer -showChoiceChangesXML -pkg /tmp/python2.pkg -target / > /tmp/python2_choices.xml
+
+    # To avoid symlink conflicts, remove tools installation in /usr/local/bin using installer choices
+    xmllint --shell /tmp/python2_choices.xml <<EOF
+    cd //array/dict[string[text()='org.python.Python.PythonUnixTools-2.7']]/integer
+    set 0
+    save
+EOF
+
+    sudo installer -applyChoiceChangesXML /tmp/python2_choices.xml -pkg /tmp/python2.pkg -target /
+
     pip install --upgrade pip
 
     echo "Install Python2 certificates"
@@ -19,10 +30,8 @@ if is_Veertu; then
     close_finder_window
 fi
 
-# Explicitly overwrite symlinks created by Python2 such as /usr/local/bin/2to3 since they conflict with symlinks from Python3
-# https://github.com/actions/runner-images/issues/2322
 echo "Brew Installing Python 3"
-brew_smart_install "python@3.11" || brew link --overwrite python@3.11
+brew_smart_install "python@3.11"
 
 echo "Installing pipx"
 export PIPX_BIN_DIR=/usr/local/opt/pipx_bin
diff --git a/images/macos/software-report/SoftwareReport.Common.psm1 b/images/macos/software-report/SoftwareReport.Common.psm1
index 55ea6d4b8..beaaa30a3 100644
--- a/images/macos/software-report/SoftwareReport.Common.psm1
+++ b/images/macos/software-report/SoftwareReport.Common.psm1
@@ -129,7 +129,7 @@ function Get-PipVersion {
         [int] $Version
     )
 
-    $command = If ($Version -eq 2) { "pip --version" } Else { "pip3 --version" }
+    $command = If ($Version -eq 2) { "/Library/Frameworks/Python.framework/Versions/2.7/bin/pip --version" } Else { "pip3 --version" }
     $commandOutput = Run-Command $command
     $versionPart1 = $commandOutput | Take-Part -Part 1
     $versionPart2 = $commandOutput | Take-Part -Part 4
@@ -192,7 +192,7 @@ function Get-PerlVersion {
 }
 
 function Get-PythonVersion {
-    $pythonVersion = Run-Command "python --version"
+    $pythonVersion = Run-Command "/Library/Frameworks/Python.framework/Versions/2.7/bin/python --version"
     return ($pythonVersion -replace "^Python").Trim()
 }
 
diff --git a/images/macos/tests/Python.Tests.ps1 b/images/macos/tests/Python.Tests.ps1
index 6433dc7db..4c1f7086e 100644
--- a/images/macos/tests/Python.Tests.ps1
+++ b/images/macos/tests/Python.Tests.ps1
@@ -30,19 +30,11 @@ Describe "Python3" -Skip:($os.IsVenturaArm64) {
 
 Describe "Python2" -Skip:($os.IsVenturaArm64 -or $os.IsVentura) {
     It "Python 2 is available" {
-        "python --version" | Should -ReturnZeroExitCode
-    }
-
-    It "Python 2 is real 2.x" {
-        (Get-CommandResult "python --version").Output | Should -BeLike "Python 2.*"
-    }
-
-    It "Python 2 is installed under /usr/local/bin" {
-        Get-WhichTool "python" | Should -BeLike "/usr/local/bin*"
+        "/Library/Frameworks/Python.framework/Versions/2.7/bin/python --version" | Should -ReturnZeroExitCode
     }
 
     It "Pip 2 is available" {
-        "pip --version" | Should -ReturnZeroExitCode
+        "/Library/Frameworks/Python.framework/Versions/2.7/bin/pip --version" | Should -ReturnZeroExitCode
     }
 
     It "2to3 symlink does not point to Python 2" {