From 2f702974cc4efe8afc258fb46b55eaac6bd8e7d7 Mon Sep 17 00:00:00 2001
From: Erik Bershel <110455084+erik-bershel@users.noreply.github.com>
Date: Thu, 16 Oct 2025 12:34:30 +0200
Subject: [PATCH] [macOS] Update Python script and Python3 symlink behaviour
 (#13174)

---
 images/macos/scripts/build/Install-Toolset.ps1 |  9 +++++++++
 images/macos/scripts/build/install-python.sh   | 10 +---------
 images/macos/scripts/tests/Python.Tests.ps1    |  7 ++++++-
 images/macos/toolsets/toolset-14.json          |  3 ---
 images/macos/toolsets/toolset-15.json          |  3 ---
 images/macos/toolsets/toolset-26.json          |  3 ---
 6 files changed, 16 insertions(+), 19 deletions(-)

diff --git a/images/macos/scripts/build/Install-Toolset.ps1 b/images/macos/scripts/build/Install-Toolset.ps1
index 1e81cd27b..a9a89665f 100644
--- a/images/macos/scripts/build/Install-Toolset.ps1
+++ b/images/macos/scripts/build/Install-Toolset.ps1
@@ -54,4 +54,13 @@ foreach ($tool in $tools) {
     }
 }
 
+
+# Ensure python3 and pip3 point to the latest installed Python version
+# Fix for ./setup.sh script behavior for python3 and pip3 symlinks
+# Only Intel images are affected since /usr/local/bin is used for Intel
+# ARM images use /opt/homebrew/bin which is managed by Homebrew
+Write-Host "Ensuring python3 and pip3 point to the latest installed Python version from Homebrew"
+brew unlink python@3.14 && brew link python@3.14 --force --overwrite
+Split-Path (readlink (which python3)) 
+
 Invoke-PesterTests "Toolcache"
diff --git a/images/macos/scripts/build/install-python.sh b/images/macos/scripts/build/install-python.sh
index 0188382f3..5f3668afb 100644
--- a/images/macos/scripts/build/install-python.sh
+++ b/images/macos/scripts/build/install-python.sh
@@ -12,16 +12,8 @@ echo "Installing Python Tooling"
 close_finder_window
 
 # Installing latest Homebrew Python 3 to handle python3 and pip3 symlinks
-# When latest Python3 is installed as a dependency for other packages
-# it does not create /usr/local/bin/python3 and /usr/local/bin/pip3
 echo "Brew Installing default Python 3"
-brew_smart_install "python"
-
-# Install specific Python version
-# Update symlinks for python3 and pip3 to point to the specific version
-toolsetVersion=$(get_toolset_value '.python.default')
-echo "Installing Python $toolsetVersion"
-brew_smart_install "python@$toolsetVersion"
+brew_smart_install "python3"
 
 # Pipx has its own Python dependency
 echo "Installing pipx"
diff --git a/images/macos/scripts/tests/Python.Tests.ps1 b/images/macos/scripts/tests/Python.Tests.ps1
index 0100e9caa..d5a7d3ad7 100644
--- a/images/macos/scripts/tests/Python.Tests.ps1
+++ b/images/macos/scripts/tests/Python.Tests.ps1
@@ -26,10 +26,15 @@ Describe "Python3" {
         "pipx --version" | Should -ReturnZeroExitCode
     }
 
-    It "Pip 3 and Python 3 came from the same brew formula" {
+    It "Pip 3 and Python 3 came from the same path prefix" {
         $pip3Path = Split-Path (readlink (which pip3))
         $python3Path = Split-Path (readlink (which python3))
         $pip3Path | Should -BeExactly $python3Path
     }
 
+    It "Pip 3 and Python 3 came from brew formula" {
+        Split-Path (readlink (which pip3))    | Should -BeLike "*/Cellar/*"
+        Split-Path (readlink (which python3)) | Should -BeLike "*/Cellar/*"
+    }
+
 }
diff --git a/images/macos/toolsets/toolset-14.json b/images/macos/toolsets/toolset-14.json
index bf94c2568..33dfe5be9 100644
--- a/images/macos/toolsets/toolset-14.json
+++ b/images/macos/toolsets/toolset-14.json
@@ -222,9 +222,6 @@
             "fastlane"
         ]
     },
-    "python": {
-        "default": "3.13"
-    },
     "toolcache": [
         {
             "name": "Python",
diff --git a/images/macos/toolsets/toolset-15.json b/images/macos/toolsets/toolset-15.json
index be5c180e3..5d3c259f6 100644
--- a/images/macos/toolsets/toolset-15.json
+++ b/images/macos/toolsets/toolset-15.json
@@ -226,9 +226,6 @@
             "fastlane"
         ]
     },
-    "python": {
-        "default": "3.13"
-    },
     "toolcache": [
         {
             "name": "Python",
diff --git a/images/macos/toolsets/toolset-26.json b/images/macos/toolsets/toolset-26.json
index 34c56fb58..0a346018b 100644
--- a/images/macos/toolsets/toolset-26.json
+++ b/images/macos/toolsets/toolset-26.json
@@ -130,9 +130,6 @@
             "fastlane"
         ]
     },
-    "python": {
-        "default": "3.13"
-    },
     "toolcache": [
         {
             "name": "Python",