diff --git a/src/python/grpcio/README.rst b/src/python/grpcio/README.rst
index f047243f82d..04a3bcbc204 100644
--- a/src/python/grpcio/README.rst
+++ b/src/python/grpcio/README.rst
@@ -8,8 +8,8 @@ Installation
 
 gRPC Python is available for Linux, macOS, and Windows.
 
-From PyPI
-~~~~~~~~~
+Installing From PyPI
+~~~~~~~~~~~~~~~~~~~~
 
 If you are installing locally...
 
@@ -37,8 +37,8 @@ n.b. On Windows and on Mac OS X one *must* have a recent release of :code:`pip`
 to retrieve the proper wheel from PyPI. Be sure to upgrade to the latest
 version!
 
-From Source
-~~~~~~~~~~~
+Installing From Source
+~~~~~~~~~~~~~~~~~~~~~~
 
 Building from source requires that you have the Python headers (usually a
 package named :code:`python-dev`).
diff --git a/tools/distrib/python/grpcio_tools/README.rst b/tools/distrib/python/grpcio_tools/README.rst
index 32873b291fa..17816deff61 100644
--- a/tools/distrib/python/grpcio_tools/README.rst
+++ b/tools/distrib/python/grpcio_tools/README.rst
@@ -9,8 +9,8 @@ Installation
 The gRPC Python tools package is available for Linux, Mac OS X, and Windows
 running Python 2.7.
 
-From PyPI
-~~~~~~~~~
+Installing From PyPI
+~~~~~~~~~~~~~~~~~~~~
 
 If you are installing locally...
 
@@ -42,8 +42,8 @@ You might also need to install Cython to handle installation via the source
 distribution if gRPC Python's system coverage with wheels does not happen to
 include your system.
 
-From Source
-~~~~~~~~~~~
+Installing From Source
+~~~~~~~~~~~~~~~~~~~~~~
 
 Building from source requires that you have the Python headers (usually a
 package named :code:`python-dev`) and Cython installed. It further requires a
diff --git a/tools/run_tests/artifacts/build_artifact_python.bat b/tools/run_tests/artifacts/build_artifact_python.bat
index 795e80dc40d..c946cd98061 100644
--- a/tools/run_tests/artifacts/build_artifact_python.bat
+++ b/tools/run_tests/artifacts/build_artifact_python.bat
@@ -46,6 +46,10 @@ pushd tools\distrib\python\grpcio_tools
 python setup.py bdist_wheel || goto :error
 popd
 
+@rem Ensure the generate artifacts are valid.
+python -m pip install twine
+python -m twine check dist\* tools\distrib\python\grpcio_tools\dist\* || goto :error
+
 xcopy /Y /I /S dist\* %ARTIFACT_DIR% || goto :error
 xcopy /Y /I /S tools\distrib\python\grpcio_tools\dist\* %ARTIFACT_DIR% || goto :error
 
diff --git a/tools/run_tests/artifacts/build_artifact_python.sh b/tools/run_tests/artifacts/build_artifact_python.sh
index e451ced338f..c5e380fe5dc 100755
--- a/tools/run_tests/artifacts/build_artifact_python.sh
+++ b/tools/run_tests/artifacts/build_artifact_python.sh
@@ -130,5 +130,11 @@ then
   cp -r src/python/grpcio_status/dist/* "$ARTIFACT_DIR"
 fi
 
+# Ensure the generated artifacts are valid.
+"${PYTHON}" -m virtualenv venv || { "${PYTHON}" -m pip install virtualenv && "${PYTHON}" -m virtualenv venv; }
+venv/bin/python -m pip install twine
+venv/bin/python -m twine check dist/* tools/distrib/python/grpcio_tools/dist/*
+rm -rf venv/
+
 cp -r dist/* "$ARTIFACT_DIR"
 cp -r tools/distrib/python/grpcio_tools/dist/* "$ARTIFACT_DIR"