diff --git a/.github/workflows/test-system.yml b/.github/workflows/test-system.yml
index d3daaf5ed..1c669a55e 100644
--- a/.github/workflows/test-system.yml
+++ b/.github/workflows/test-system.yml
@@ -523,24 +523,28 @@ jobs:
     timeout-minutes: 10
     name: "python3.9 via chocolatey"
     runs-on: windows-latest
+    env:
+      TEST_PYTHON_VERSION: "3.9.13"
     steps:
       - uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
         with:
           persist-credentials: false
 
       - name: "Install Python"
-        run: choco install python3 --verbose --version=3.9.13
+        run: choco install python3 --verbose --version=$env:TEST_PYTHON_VERSION
 
       - name: "Download binary"
         uses: actions/download-artifact@d3f86a106a0bac45b974a628896c90dbdf5c8093 # v4.3.0
         with:
           name: uv-windows-x86_64-${{ inputs.sha }}
 
-      - name: "Print Python path"
-        run: echo $(which python3)
-
+      # Chocolatey updates the registry but doesn't update `GITHUB_PATH` and since figuring out what
+      # it added would be more work than it's worth, it's simpler to just reload the values from the
+      # registry.
       - name: "Validate global Python install"
-        run: py -3.9 ./scripts/check_system_python.py --uv ./uv.exe
+        run: |
+          $env:PATH = [System.Environment]::GetEnvironmentVariable("Path","Machine") + ";" + [System.Environment]::GetEnvironmentVariable("Path","User")
+          python ./scripts/check_system_python.py --uv ./uv.exe --check-python-version $env:TEST_PYTHON_VERSION --check-path
 
   system-test-pyenv:
     timeout-minutes: 10
diff --git a/scripts/check_system_python.py b/scripts/check_system_python.py
index fbfc5557e..090ed47fb 100755
--- a/scripts/check_system_python.py
+++ b/scripts/check_system_python.py
@@ -52,6 +52,17 @@ if __name__ == "__main__":
         required=False,
         help="Set if the system Python version must be explicitly specified, e.g., for prereleases.",
     )
+    parser.add_argument(
+        "--check-python-version",
+        required=False,
+        help="Verify that this tool has been started with the specified python version. Omitting the patch number will match any patch number.",
+    )
+    parser.add_argument(
+        "--check-path",
+        required=False,
+        action="store_true",
+        help="Attempt to verify that the PATH is set up so that this tool's python will match the python version that uv would automatically pick up.",
+    )
     args = parser.parse_args()
 
     uv: str = os.path.abspath(args.uv) if args.uv else "uv"
@@ -60,6 +71,29 @@ if __name__ == "__main__":
     )
     python = ["--python", args.python] if args.python else []
 
+    if args.check_python_version:
+        version = ".".join(map(str, sys.version_info[:3]))
+        if args.check_python_version != version and not version.startswith(
+            args.check_python_version + "."
+        ):
+            raise Exception(
+                f"Expected to be running {args.check_python_version} but we are on {version}."
+            )
+
+    if args.check_path:
+        process = subprocess.run(
+            ["python", "-c", "import sys; print(sys.executable)"],
+            check=True,
+            stdout=subprocess.PIPE,
+        )
+        system_python_path = os.path.normcase(os.path.normpath(process.stdout))
+        our_python_path = os.path.normcase(os.path.normpath(sys.executable))
+
+        if our_python_path != system_python_path:
+            raise Exception(
+                f"Script was ran with {our_python_path} but `python` resolves to {system_python_path}"
+            )
+
     # Create a temporary directory.
     with tempfile.TemporaryDirectory() as temp_dir:
         # Ensure that the package (`pylint`) isn't installed.