diff --git a/requirements.txt b/requirements.txt
index 00d91d3c13d..5d8840e8863 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -1,7 +1,6 @@
 # GRPC Python setup requirements
 coverage>=4.0
 cython>=0.29.8
-enum34>=1.0.4
 protobuf>=3.5.0.post1, < 4.0dev
 six>=1.10
 wheel>=0.29
diff --git a/src/python/grpcio_tests/setup.py b/src/python/grpcio_tests/setup.py
index 81890a1a202..87cccda425b 100644
--- a/src/python/grpcio_tests/setup.py
+++ b/src/python/grpcio_tests/setup.py
@@ -38,8 +38,7 @@ PACKAGE_DIRECTORIES = {
 }
 
 INSTALL_REQUIRES = (
-    'coverage>=4.0', 'enum34>=1.0.4',
-    'grpcio>={version}'.format(version=grpc_version.VERSION),
+    'coverage>=4.0', 'grpcio>={version}'.format(version=grpc_version.VERSION),
     'grpcio-channelz>={version}'.format(version=grpc_version.VERSION),
     'grpcio-status>={version}'.format(version=grpc_version.VERSION),
     'grpcio-tools>={version}'.format(version=grpc_version.VERSION),
@@ -48,7 +47,7 @@ INSTALL_REQUIRES = (
     'google-auth>=1.17.2', 'requests>=2.14.2')
 
 if not PY3:
-    INSTALL_REQUIRES += ('futures>=2.2.0',)
+    INSTALL_REQUIRES += ('futures>=2.2.0', 'enum34>=1.0.4')
 
 COMMAND_CLASS = {
     # Run `preprocess` *before* doing any packaging!
diff --git a/tools/internal_ci/helper_scripts/prepare_build_macos_rc b/tools/internal_ci/helper_scripts/prepare_build_macos_rc
index e7bc43946c9..635f19596f2 100644
--- a/tools/internal_ci/helper_scripts/prepare_build_macos_rc
+++ b/tools/internal_ci/helper_scripts/prepare_build_macos_rc
@@ -89,9 +89,9 @@ then
   # python
   time pip install --user virtualenv
   time pip install --user --upgrade Mako six tox setuptools==44.1.1 twisted pyyaml pyjwt cryptography requests
-  export PYTHONPATH=/Library/Python/3.4/site-packages
 
   # make sure md5sum is available (requires coreutils 8.31+)
+  brew update-reset
   brew upgrade coreutils
 
   # Install Python 3.7 and Python 3.8
diff --git a/tools/run_tests/artifacts/build_artifact_python.sh b/tools/run_tests/artifacts/build_artifact_python.sh
index abd6900152c..bf8b5ac6d95 100755
--- a/tools/run_tests/artifacts/build_artifact_python.sh
+++ b/tools/run_tests/artifacts/build_artifact_python.sh
@@ -104,7 +104,7 @@ then
 
   if [ "$("$PYTHON" -c "import sys; print(sys.version_info[0])")" == "2" ]
   then
-    "${PIP}" install futures>=2.2.0
+    "${PIP}" install futures>=2.2.0 enum34>=1.0.4
   fi
 
   "${PIP}" install grpcio --no-index --find-links "file://$ARTIFACT_DIR/"
diff --git a/tools/run_tests/helper_scripts/build_python.sh b/tools/run_tests/helper_scripts/build_python.sh
index a9a186c52bd..331f10e838a 100755
--- a/tools/run_tests/helper_scripts/build_python.sh
+++ b/tools/run_tests/helper_scripts/build_python.sh
@@ -188,11 +188,11 @@ esac
 pip_install --upgrade setuptools==44.1.1
 pip_install --upgrade pip==19.3.1
 pip_install --upgrade cython
-pip_install --upgrade six enum34 protobuf
+pip_install --upgrade six protobuf
 
 if [ "$("$VENV_PYTHON" -c "import sys; print(sys.version_info[0])")" == "2" ]
 then
-  pip_install futures
+  pip_install --upgrade futures enum34
 fi
 
 pip_install_dir "$ROOT"