diff --git a/images/macos/provision/core/python.sh b/images/macos/provision/core/python.sh
index 229922096..5fb7aff24 100755
--- a/images/macos/provision/core/python.sh
+++ b/images/macos/provision/core/python.sh
@@ -4,9 +4,6 @@ source ~/utils/utils.sh
 
 echo "Installing Python Tooling"
 
-echo "Brew Installing Python 3"
-brew install python@3.9
-
 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"
@@ -16,6 +13,11 @@ pip install --upgrade pip
 echo "Install Python2 certificates"
 bash -c "/Applications/Python\ 2.7/Install\ Certificates.command"
 
+# Explicitly overwrite symlinks created by Python2 such as /usr/local/bin/2to3 since they conflict with symlinks from Python3
+# https://github.com/actions/virtual-environments/issues/2322
+echo "Brew Installing Python 3"
+brew install python@3.9 || brew link --overwrite python@3.9
+
 echo "Installing pipx"
 export PIPX_BIN_DIR=/usr/local/opt/pipx_bin
 export PIPX_HOME=/usr/local/opt/pipx