diff --git a/tools/internal_ci/helper_scripts/install_python38.ps1 b/tools/internal_ci/helper_scripts/install_python38.ps1
index afe15b73272..e3b82fee1dc 100644
--- a/tools/internal_ci/helper_scripts/install_python38.ps1
+++ b/tools/internal_ci/helper_scripts/install_python38.ps1
@@ -2,6 +2,7 @@
 # Install Python 3.8 for x64 and x86 in order to build wheels on Windows.
 
 Set-StrictMode -Version 2
+Set-PSDebug -Trace 1
 $ErrorActionPreference = 'Stop'
 
 # Avoid "Could not create SSL/TLS secure channel"
@@ -33,6 +34,21 @@ function Install-Python {
     if (-Not $?) {
         throw "The Python installation exited with error!"
     }
+
+    # Validates Python
+    $PythonBinary = "$PythonInstallPath/python.exe"
+    while ($true) {
+        & $PythonBinary -c 'print(42)'
+        if ($?) {
+            Write-Host "Python binary works properly."
+            break
+        }
+        Start-Sleep -Seconds 1
+    }
+
+    # Installs pip
+    & $PythonBinary -m ensurepip --user
+
     Write-Host "Python $PythonVersion installed by $PythonInstaller at $PythonInstallPath."
 }
 
@@ -51,4 +67,3 @@ $Python38x64Config = @{
     PythonInstallerHash = "29ea87f24c32f5e924b7d63f8a08ee8d"
 }
 Install-Python @Python38x64Config
-
diff --git a/tools/run_tests/artifacts/artifact_targets.py b/tools/run_tests/artifacts/artifact_targets.py
index 4bf7217ac2d..0d317467b2a 100644
--- a/tools/run_tests/artifacts/artifact_targets.py
+++ b/tools/run_tests/artifacts/artifact_targets.py
@@ -173,7 +173,7 @@ class PythonArtifact:
             if 'Python27' in self.py_version:
                 environ['EXT_COMPILER'] = 'mingw32'
             else:
-                environ['EXT_COMPILER'] = 'msvc'
+                environ['EXT_COMPILER'] = 'C:\Program Files (x86)\Microsoft Visual Studio 14.0\VC\bin\cl.exe'
             # For some reason, the batch script %random% always runs with the same
             # seed.  We create a random temp-dir here
             dir = ''.join(
diff --git a/tools/run_tests/artifacts/build_artifact_python.bat b/tools/run_tests/artifacts/build_artifact_python.bat
index 88a331e2782..b1e0ee7d0fb 100644
--- a/tools/run_tests/artifacts/build_artifact_python.bat
+++ b/tools/run_tests/artifacts/build_artifact_python.bat
@@ -15,10 +15,10 @@
 @rem set path to python & mingw compiler
 set PATH=C:\%1;C:\%1\scripts;C:\msys64\mingw%2\bin;C:\tools\msys64\mingw%2\bin;%PATH%
 
-pip install --upgrade six
+python -m pip install --upgrade six
 @rem some artifacts are broken for setuptools 38.5.0. See https://github.com/grpc/grpc/issues/14317
-pip install --upgrade setuptools==38.2.4
-pip install -rrequirements.txt
+python -m pip install --upgrade setuptools==38.2.4
+python -m pip install -rrequirements.txt
 
 set GRPC_PYTHON_BUILD_WITH_CYTHON=1