diff --git a/.bazelrc b/.bazelrc
index 9dc181237c..4345f50815 100644
--- a/.bazelrc
+++ b/.bazelrc
@@ -18,3 +18,5 @@ build --incompatible_default_to_explicit_init_py
 
 # Windows makes use of runfiles for some rules
 build --enable_runfiles
+# TODO(f0rmiga): remove this so that other features don't start relying on it.
+startup --windows_enable_symlinks
diff --git a/python/repositories.bzl b/python/repositories.bzl
index 8b2e3cf051..520dda15f5 100644
--- a/python/repositories.bzl
+++ b/python/repositories.bzl
@@ -98,6 +98,7 @@ filegroup(
     name = "files",
     srcs = glob(
         include = [
+            "*.exe",
             "bin/**",
             "DLLs/**",
             "extensions/**",
diff --git a/python/tests/toolchains/defs.bzl b/python/tests/toolchains/defs.bzl
index 939214876f..81cbe20b5d 100644
--- a/python/tests/toolchains/defs.bzl
+++ b/python/tests/toolchains/defs.bzl
@@ -17,6 +17,12 @@
 
 load("//python:versions.bzl", "PLATFORMS", "TOOL_VERSIONS")
 
+_WINDOWS_RUNNER_TEMPLATE = """\
+@ECHO OFF
+set PATHEXT=.COM;.EXE;.BAT
+powershell.exe -c "& ./{interpreter_path} {run_acceptance_test_py}"
+"""
+
 def _acceptance_test_impl(ctx):
     workspace = ctx.actions.declare_file("/".join([ctx.attr.python_version, "WORKSPACE"]))
     ctx.actions.expand_template(
@@ -52,7 +58,8 @@ def _acceptance_test_impl(ctx):
         },
     )
 
-    py3_runtime = ctx.toolchains["@bazel_tools//tools/python:toolchain_type"].py3_runtime
+    toolchain = ctx.toolchains["@bazel_tools//tools/python:toolchain_type"]
+    py3_runtime = toolchain.py3_runtime
     interpreter_path = py3_runtime.interpreter_path
     if not interpreter_path:
         interpreter_path = py3_runtime.interpreter.short_path
@@ -61,9 +68,9 @@ def _acceptance_test_impl(ctx):
         executable = ctx.actions.declare_file("run_test_{}.bat".format(ctx.attr.python_version))
         ctx.actions.write(
             output = executable,
-            content = "call {interpreter_path} {run_acceptance_test_py}".format(
-                interpreter_path = interpreter_path.replace("/", "\\"),
-                run_acceptance_test_py = run_acceptance_test_py.short_path.replace("/", "\\"),
+            content = _WINDOWS_RUNNER_TEMPLATE.format(
+                interpreter_path = interpreter_path.replace("../", "external/"),
+                run_acceptance_test_py = run_acceptance_test_py.short_path,
             ),
             is_executable = True,
         )
@@ -96,26 +103,40 @@ def _acceptance_test_impl(ctx):
     )]
 
 _acceptance_test = rule(
-    _acceptance_test_impl,
+    implementation = _acceptance_test_impl,
+    doc = "TODO",
     attrs = {
-        "is_windows": attr.bool(mandatory = True),
-        "python_version": attr.string(mandatory = True),
-        "test_location": attr.string(mandatory = True),
+        "is_windows": attr.bool(
+            doc = "TODO",
+            mandatory = True,
+        ),
+        "python_version": attr.string(
+            doc = "TODO",
+            mandatory = True,
+        ),
+        "test_location": attr.string(
+            doc = "TODO",
+            mandatory = True,
+        ),
         "_build_bazel_tmpl": attr.label(
+            doc = "TODO",
             allow_single_file = True,
-            default = "//python/tests/toolchains/workspace_template:BUILD.bazel.tmpl",
+            default = Label("//python/tests/toolchains/workspace_template:BUILD.bazel.tmpl"),
         ),
         "_python_version_test": attr.label(
+            doc = "TODO",
             allow_single_file = True,
-            default = "//python/tests/toolchains/workspace_template:python_version_test.py",
+            default = Label("//python/tests/toolchains/workspace_template:python_version_test.py"),
         ),
         "_run_acceptance_test": attr.label(
+            doc = "TODO",
             allow_single_file = True,
-            default = "//python/tests/toolchains:run_acceptance_test.py",
+            default = Label("//python/tests/toolchains:run_acceptance_test.py"),
         ),
         "_workspace_tmpl": attr.label(
+            doc = "TODO",
             allow_single_file = True,
-            default = "//python/tests/toolchains/workspace_template:WORKSPACE.tmpl",
+            default = Label("//python/tests/toolchains/workspace_template:WORKSPACE.tmpl"),
         ),
     },
     test = True,
diff --git a/python/tests/toolchains/run_acceptance_test.py b/python/tests/toolchains/run_acceptance_test.py
index 4a7afd74df..8238710c67 100644
--- a/python/tests/toolchains/run_acceptance_test.py
+++ b/python/tests/toolchains/run_acceptance_test.py
@@ -14,23 +14,49 @@
 
 import os
 import subprocess
+import sys
+import tempfile
 import unittest
 
 
 class TestPythonVersion(unittest.TestCase):
+    @classmethod
+    def setUpClass(cls):
+        os.chdir("%test_location%")
+        python_version_test_dirname = os.path.dirname(
+            os.path.realpath("python_version_test.py")
+        )
+        rules_python_path = os.path.normpath(
+            os.path.join(python_version_test_dirname, "..", "..", "..", "..")
+        )
+
+        is_windows = "win" in sys.platform
+        if is_windows:
+            newline = "\r\n"
+            os.environ["HOME"] = tempfile.mkdtemp()
+            os.environ["LocalAppData"] = tempfile.mkdtemp()
+        else:
+            newline = "\n"
+
+        with open(".bazelrc", "w") as bazelrc:
+            bazelrc.write(
+                newline.join(
+                    [
+                        'build --override_repository rules_python="{}"'.format(
+                            rules_python_path.replace("\\", "/")
+                        ),
+                        "build --test_output=errors",
+                    ]
+                )
+            )
+
     def test_match_toolchain(self):
         stream = os.popen("bazel run @python_toolchain_host//:python3 -- --version")
-        output = stream.read()
-        self.assertEqual(output, "Python %python_version%\n")
+        output = stream.read().strip()
+        self.assertEqual(output, "Python %python_version%")
 
         subprocess.run("bazel test //...", shell=True, check=True)
 
 
 if __name__ == "__main__":
-    os.chdir("%test_location%")
-    python_version_test_dirname = os.path.dirname(os.path.realpath("python_version_test.py"))
-    rules_python_path = os.path.join(python_version_test_dirname, "..", "..", "..", "..")
-    with open(".bazelrc", "w") as bazelrc:
-        bazelrc.write("build --override_repository rules_python=\"{}\"\n".format(rules_python_path))
-        bazelrc.write("build --test_output=errors\n")
     unittest.main()