diff --git a/WORKSPACE b/WORKSPACE
index 52847be6068..da870cbebcd 100644
--- a/WORKSPACE
+++ b/WORKSPACE
@@ -95,15 +95,9 @@ rbe_autoconfig(
     ),
 )
 
-load("@io_bazel_rules_python//python:pip.bzl", "pip_import", "pip_repositories")
+load("@io_bazel_rules_python//python:pip.bzl", "pip_install")
 
-pip_import(
+pip_install(
     name = "grpc_python_dependencies",
     requirements = "@com_github_grpc_grpc//:requirements.bazel.txt",
 )
-
-load("@grpc_python_dependencies//:requirements.bzl", "pip_install")
-
-pip_repositories()
-
-pip_install()
diff --git a/bazel/BUILD b/bazel/BUILD
index f94b9824360..aa6cb341dfe 100644
--- a/bazel/BUILD
+++ b/bazel/BUILD
@@ -17,3 +17,8 @@ licenses(["notice"])
 package(default_visibility = ["//:__subpackages__"])
 
 load(":cc_grpc_library.bzl", "cc_grpc_library")
+
+filegroup(
+    name = "_gevent_test_main",
+    srcs = ["_gevent_test_main.py"],
+)
diff --git a/bazel/_gevent_test_main.py b/bazel/_gevent_test_main.py
new file mode 100644
index 00000000000..52629c61d3c
--- /dev/null
+++ b/bazel/_gevent_test_main.py
@@ -0,0 +1,60 @@
+# Copyright 2021 The gRPC Authors
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+import grpc
+import unittest
+import sys
+import os
+import pkgutil
+
+from typing import Sequence
+
+class SingleLoader(object):
+    def __init__(self, pattern: str):
+        loader = unittest.TestLoader()
+        self.suite = unittest.TestSuite()
+        tests = []
+        for importer, module_name, is_package in pkgutil.walk_packages([os.path.dirname(os.path.relpath(__file__))]):
+            if pattern in module_name:
+                module = importer.find_module(module_name).load_module(module_name)
+                tests.append(loader.loadTestsFromModule(module))
+        if len(tests) != 1:
+            raise AssertionError("Expected only 1 test module. Found {}".format(tests))
+        self.suite.addTest(tests[0])
+
+
+    def loadTestsFromNames(self, names: Sequence[str], module: str = None) -> unittest.TestSuite:
+        return self.suite
+
+if __name__ == "__main__":
+    from gevent import monkey
+
+    monkey.patch_all()
+
+    import grpc.experimental.gevent
+    grpc.experimental.gevent.init_gevent()
+    import gevent
+
+    if len(sys.argv) != 2:
+        print(f"USAGE: {sys.argv[0]} TARGET_MODULE", file=sys.stderr)
+
+    target_module = sys.argv[1]
+
+    loader = SingleLoader(target_module)
+    runner = unittest.TextTestRunner()
+
+    result = gevent.spawn(runner.run, loader.suite)
+    result.join()
+    if not result.value.wasSuccessful():
+        sys.exit("Test failure.")
diff --git a/bazel/gevent_test.bzl b/bazel/gevent_test.bzl
new file mode 100644
index 00000000000..55444d32195
--- /dev/null
+++ b/bazel/gevent_test.bzl
@@ -0,0 +1,71 @@
+# Copyright 2021 The gRPC Authors
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+load("@grpc_python_dependencies//:requirements.bzl", "requirement")
+
+_GRPC_LIB = "//src/python/grpcio/grpc:grpcio"
+
+_COPIED_MAIN_SUFFIX = ".gevent.main"
+
+def py_grpc_gevent_test(
+        name,
+        srcs,
+        main = None,
+        deps = None,
+        data = None,
+        **kwargs):
+    if main == None:
+        if len(srcs) != 1:
+            fail("When main is not provided, srcs must be of size 1.")
+        main = srcs[0]
+    deps = [] if deps == None else deps
+    data = [] if data == None else data
+    lib_name = name + ".gevent.lib"
+    supplied_python_version = kwargs.pop("python_version", "")
+    if supplied_python_version and supplied_python_version != "PY3":
+        fail("py_grpc_gevent_test only supports python_version=PY3")
+    native.py_library(
+        name = lib_name,
+        srcs = srcs,
+    )
+    augmented_deps = deps + [
+        ":{}".format(lib_name),
+        requirement("gevent"),
+    ]
+    if _GRPC_LIB not in augmented_deps:
+        augmented_deps.append(_GRPC_LIB)
+
+    # The main file needs to be in the same package as the test file.
+    copied_main_name = name + _COPIED_MAIN_SUFFIX
+    copied_main_filename = copied_main_name + ".py"
+    native.genrule(
+        name = copied_main_name,
+        srcs = ["//bazel:_gevent_test_main.py"],
+        outs = [copied_main_filename],
+        cmd = "cp $< $@",
+    )
+
+    # TODO(https://github.com/grpc/grpc/issues/27542): Remove once gevent is deemed non-flaky.
+    if "flaky" in kwargs:
+        kwargs.pop("flaky")
+
+    native.py_test(
+        name = name + ".gevent",
+        args = [name],
+        deps = augmented_deps,
+        srcs = [copied_main_filename],
+        main = copied_main_filename,
+        python_version = "PY3",
+        flaky = True,
+        **kwargs
+    )
diff --git a/bazel/grpc_python_deps.bzl b/bazel/grpc_python_deps.bzl
index 4c47c5c1186..bbbaa2a1bb9 100644
--- a/bazel/grpc_python_deps.bzl
+++ b/bazel/grpc_python_deps.bzl
@@ -49,8 +49,10 @@ def grpc_python_deps():
     if "io_bazel_rules_python" not in native.existing_rules():
         http_archive(
             name = "io_bazel_rules_python",
-            url = "https://github.com/bazelbuild/rules_python/releases/download/0.0.1/rules_python-0.0.1.tar.gz",
-            sha256 = "aa96a691d3a8177f3215b14b0edc9641787abaaa30363a080165d06ab65e1161",
+            url = "https://github.com/bazelbuild/rules_python/releases/download/0.4.0/rules_python-0.4.0.tar.gz",
+            sha256 = "954aa89b491be4a083304a2cb838019c8b8c3720a7abb9c4cb81ac7a24230cea",
+            patches = ["//third_party:rules_python.patch"],
+            patch_args = ["-p1"],
         )
 
     python_configure(name = "local_config_python")
diff --git a/bazel/internal_python_rules.bzl b/bazel/internal_python_rules.bzl
new file mode 100644
index 00000000000..6f3c8751b0d
--- /dev/null
+++ b/bazel/internal_python_rules.bzl
@@ -0,0 +1,35 @@
+# Copyright 2021 The gRPC Authors
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+"""Python-related rules intended only for use internal to the repo."""
+
+load("//bazel:gevent_test.bzl", "py_grpc_gevent_test")
+load("//bazel:python_rules.bzl", "py2and3_test")
+
+def internal_py_grpc_test(name, **kwargs):
+    """Runs a test under all supported environments."""
+    py2and3_test(name, **kwargs)
+    py_grpc_gevent_test(name, **kwargs)
+
+    suite_kwargs = {}
+    if "visibility" in kwargs:
+        suite_kwargs["visibility"] = kwargs["visibility"]
+
+    native.test_suite(
+        name = name,
+        tests = [
+            name + ".both_pythons",
+            name + ".gevent",
+        ],
+        **suite_kwargs
+    )
diff --git a/bazel/python_rules.bzl b/bazel/python_rules.bzl
index df067d36abb..68137bd21d8 100644
--- a/bazel/python_rules.bzl
+++ b/bazel/python_rules.bzl
@@ -268,6 +268,7 @@ def py_grpc_library(
         **kwargs
     )
 
+# TODO(https://github.com/grpc/grpc/issues/27543): Remove once Python 2 is no longer supported.
 def py2and3_test(
         name,
         py_test = native.py_test,
@@ -297,7 +298,7 @@ def py2and3_test(
         suite_kwargs["visibility"] = kwargs["visibility"]
 
     native.test_suite(
-        name = name,
+        name = name + ".both_pythons",
         tests = names,
         **suite_kwargs
     )
diff --git a/requirements.bazel.txt b/requirements.bazel.txt
index 57deb95420a..e24eca17797 100644
--- a/requirements.bazel.txt
+++ b/requirements.bazel.txt
@@ -14,3 +14,6 @@ chardet==3.0.4
 certifi==2017.4.17
 idna==2.7
 googleapis-common-protos==1.5.5
+gevent==21.1.2
+zope.event==4.5.0
+setuptools==44.1.1
diff --git a/src/python/grpcio_tests/tests/unit/BUILD.bazel b/src/python/grpcio_tests/tests/unit/BUILD.bazel
index 67d7a900318..bf8bdef0e38 100644
--- a/src/python/grpcio_tests/tests/unit/BUILD.bazel
+++ b/src/python/grpcio_tests/tests/unit/BUILD.bazel
@@ -11,7 +11,7 @@
 # WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 # See the License for the specific language governing permissions and
 # limitations under the License.
-load("//bazel:python_rules.bzl", "py2and3_test")
+load("//bazel:internal_python_rules.bzl", "internal_py_grpc_test")
 
 package(default_visibility = ["//visibility:public"])
 
@@ -105,7 +105,7 @@ py_library(
 )
 
 [
-    py2and3_test(
+    internal_py_grpc_test(
         name = test_file_name[:-3],
         size = "small",
         srcs = [test_file_name],
@@ -133,7 +133,7 @@ py_library(
     for test_file_name in GRPCIO_TESTS_UNIT
 ]
 
-py2and3_test(
+internal_py_grpc_test(
     name = "_dynamic_stubs_test",
     size = "small",
     srcs = ["_dynamic_stubs_test.py"],
@@ -144,6 +144,7 @@ py2and3_test(
     imports = ["../../"],
     main = "_dynamic_stubs_test.py",
     deps = [
+        ":test_common",
         "//src/python/grpcio/grpc:grpcio",
         "//src/python/grpcio_tests/tests/testing",
         "//tools/distrib/python/grpcio_tools:grpc_tools",
diff --git a/src/python/grpcio_tests/tests/unit/_compression_test.py b/src/python/grpcio_tests/tests/unit/_compression_test.py
index 9789afbfe7f..cd55db58baf 100644
--- a/src/python/grpcio_tests/tests/unit/_compression_test.py
+++ b/src/python/grpcio_tests/tests/unit/_compression_test.py
@@ -259,6 +259,8 @@ def _stream_stream_client(channel, multicallable_kwargs, message):
                 i, response))
 
 
+@unittest.skipIf(test_common.running_under_gevent(),
+                 "This test is nondeterministic under gevent.")
 class CompressionTest(unittest.TestCase):
 
     def assertCompressed(self, compression_ratio):
diff --git a/src/python/grpcio_tests/tests/unit/_contextvars_propagation_test.py b/src/python/grpcio_tests/tests/unit/_contextvars_propagation_test.py
index 9c94be5a1da..128ec514d06 100644
--- a/src/python/grpcio_tests/tests/unit/_contextvars_propagation_test.py
+++ b/src/python/grpcio_tests/tests/unit/_contextvars_propagation_test.py
@@ -97,6 +97,8 @@ else:
 
 # TODO(https://github.com/grpc/grpc/issues/22257)
 @unittest.skipIf(os.name == "nt", "LocalCredentials not supported on Windows.")
+@unittest.skipIf(test_common.running_under_gevent(),
+                 "ThreadLocals do not work under gevent.")
 class ContextVarsPropagationTest(unittest.TestCase):
 
     def test_propagation_to_auth_plugin(self):
diff --git a/src/python/grpcio_tests/tests/unit/_dynamic_stubs_test.py b/src/python/grpcio_tests/tests/unit/_dynamic_stubs_test.py
index 4645f0b633f..933a8143eda 100644
--- a/src/python/grpcio_tests/tests/unit/_dynamic_stubs_test.py
+++ b/src/python/grpcio_tests/tests/unit/_dynamic_stubs_test.py
@@ -21,6 +21,8 @@ import os
 import sys
 import unittest
 
+from tests.unit import test_common
+
 _DATA_DIR = os.path.join("tests", "unit", "data")
 
 
@@ -124,6 +126,8 @@ def _test_grpc_tools_unimportable():
 # when they do not come from the "__main__" module, so this test passes
 # if run directly on Windows, but not if started by the test runner.
 @unittest.skipIf(os.name == "nt", "Windows multiprocessing unsupported")
+@unittest.skipIf(test_common.running_under_gevent(),
+                 "Import paths do not work with gevent runner.")
 class DynamicStubTest(unittest.TestCase):
 
     def test_sunny_day(self):
diff --git a/src/python/grpcio_tests/tests/unit/_local_credentials_test.py b/src/python/grpcio_tests/tests/unit/_local_credentials_test.py
index ce92feed4b3..5351a2b4cc1 100644
--- a/src/python/grpcio_tests/tests/unit/_local_credentials_test.py
+++ b/src/python/grpcio_tests/tests/unit/_local_credentials_test.py
@@ -19,6 +19,8 @@ import unittest
 
 import grpc
 
+from tests.unit import test_common
+
 
 class _GenericHandler(grpc.GenericRpcHandler):
 
@@ -56,6 +58,8 @@ class LocalCredentialsTest(unittest.TestCase):
 
     @unittest.skipIf(os.name == 'nt',
                      'Unix Domain Socket is not supported on Windows')
+    @unittest.skipIf(test_common.running_under_gevent(),
+                     'UDS not supported under gevent.')
     def test_uds(self):
         server_addr = 'unix:/tmp/grpc_fullstack_test'
         channel_creds = grpc.local_channel_credentials(
diff --git a/src/python/grpcio_tests/tests/unit/_metadata_code_details_test.py b/src/python/grpcio_tests/tests/unit/_metadata_code_details_test.py
index 89c028b307b..87441833c17 100644
--- a/src/python/grpcio_tests/tests/unit/_metadata_code_details_test.py
+++ b/src/python/grpcio_tests/tests/unit/_metadata_code_details_test.py
@@ -188,6 +188,8 @@ def _generic_handler(servicer):
     return grpc.method_handlers_generic_handler(_SERVICE, method_handlers)
 
 
+@unittest.skipIf(test_common.running_under_gevent(),
+                 "Causes deadlock in gevent.")
 class MetadataCodeDetailsTest(unittest.TestCase):
 
     def setUp(self):
diff --git a/src/python/grpcio_tests/tests/unit/_reconnect_test.py b/src/python/grpcio_tests/tests/unit/_reconnect_test.py
index 90d010b9360..62ab5a58fc6 100644
--- a/src/python/grpcio_tests/tests/unit/_reconnect_test.py
+++ b/src/python/grpcio_tests/tests/unit/_reconnect_test.py
@@ -21,6 +21,7 @@ import unittest
 import grpc
 from grpc.framework.foundation import logging_pool
 
+from tests.unit import test_common
 from tests.unit.framework.common import bound_socket
 from tests.unit.framework.common import test_constants
 
@@ -34,6 +35,8 @@ def _handle_unary_unary(unused_request, unused_servicer_context):
     return _RESPONSE
 
 
+@unittest.skipIf(test_common.running_under_gevent(),
+                 "Test is nondeterministic under gevent.")
 class ReconnectTest(unittest.TestCase):
 
     def test_reconnect(self):
diff --git a/src/python/grpcio_tests/tests/unit/_rpc_part_1_test.py b/src/python/grpcio_tests/tests/unit/_rpc_part_1_test.py
index 1f85cd6f91e..0ffa9eff94f 100644
--- a/src/python/grpcio_tests/tests/unit/_rpc_part_1_test.py
+++ b/src/python/grpcio_tests/tests/unit/_rpc_part_1_test.py
@@ -22,6 +22,7 @@ import unittest
 import grpc
 from grpc.framework.foundation import logging_pool
 
+from tests.unit import test_common
 from tests.unit._rpc_test_helpers import BaseRPCTest
 from tests.unit._rpc_test_helpers import Callback
 from tests.unit._rpc_test_helpers import TIMEOUT_SHORT
@@ -36,6 +37,8 @@ from tests.unit._rpc_test_helpers import unary_unary_multi_callable
 from tests.unit.framework.common import test_constants
 
 
+@unittest.skipIf(test_common.running_under_gevent(),
+                 "This test is nondeterministic under gevent.")
 class RPCPart1Test(BaseRPCTest, unittest.TestCase):
 
     def testExpiredStreamRequestBlockingUnaryResponse(self):
diff --git a/src/python/grpcio_tests/tests/unit/_rpc_part_2_test.py b/src/python/grpcio_tests/tests/unit/_rpc_part_2_test.py
index a8e6ddeb534..6a82a9588f6 100644
--- a/src/python/grpcio_tests/tests/unit/_rpc_part_2_test.py
+++ b/src/python/grpcio_tests/tests/unit/_rpc_part_2_test.py
@@ -22,6 +22,7 @@ import unittest
 import grpc
 from grpc.framework.foundation import logging_pool
 
+from tests.unit import test_common
 from tests.unit._rpc_test_helpers import BaseRPCTest
 from tests.unit._rpc_test_helpers import Callback
 from tests.unit._rpc_test_helpers import TIMEOUT_SHORT
@@ -36,6 +37,8 @@ from tests.unit._rpc_test_helpers import unary_unary_multi_callable
 from tests.unit.framework.common import test_constants
 
 
+@unittest.skipIf(test_common.running_under_gevent(),
+                 "Causes deadlock under gevent.")
 class RPCPart2Test(BaseRPCTest, unittest.TestCase):
 
     def testDefaultThreadPoolIsUsed(self):
diff --git a/src/python/grpcio_tests/tests/unit/test_common.py b/src/python/grpcio_tests/tests/unit/test_common.py
index 3b1e3442478..dae69cbcebc 100644
--- a/src/python/grpcio_tests/tests/unit/test_common.py
+++ b/src/python/grpcio_tests/tests/unit/test_common.py
@@ -132,3 +132,14 @@ class WaitGroup(object):
         while self.count > 0:
             self.cv.wait()
         self.cv.release()
+
+
+def running_under_gevent():
+    try:
+        from gevent import monkey
+        import gevent.socket
+    except ImportError:
+        return False
+    else:
+        import socket
+        return socket.socket is gevent.socket.socket
diff --git a/third_party/BUILD b/third_party/BUILD
index 272d2396003..0ac04511a57 100644
--- a/third_party/BUILD
+++ b/third_party/BUILD
@@ -12,4 +12,5 @@ exports_files([
     "futures.BUILD",
     "libuv.BUILD",
     "protobuf.patch",
+    "rules_python.patch",
 ])
diff --git a/third_party/rules_python.patch b/third_party/rules_python.patch
new file mode 100644
index 00000000000..3b2b5b8d0df
--- /dev/null
+++ b/third_party/rules_python.patch
@@ -0,0 +1,76 @@
+diff --git a/python/pip_install/pip_repository.bzl b/python/pip_install/pip_repository.bzl
+index c3007e1..f8a9234 100644
+--- a/python/pip_install/pip_repository.bzl
++++ b/python/pip_install/pip_repository.bzl
+@@ -39,7 +39,8 @@ def _resolve_python_interpreter(rctx):
+         if "/" not in python_interpreter:
+             python_interpreter = rctx.which(python_interpreter)
+         if not python_interpreter:
+-            fail("python interpreter not found")
++            print("WARNING: python interpreter not found. Python targets will not be functional")
++            return ""
+     return python_interpreter
+ 
+ def _parse_optional_attrs(rctx, args):
+@@ -93,13 +94,49 @@ def _parse_optional_attrs(rctx, args):
+ 
+     return args
+ 
++def _generate_stub_requirements_bzl(rctx):
++    contents = """\
++def requirement(name):
++    return "@{repo}//:empty"
++""".format(repo=rctx.attr.name)
++    rctx.file("requirements.bzl", contents)
++
+ _BUILD_FILE_CONTENTS = """\
+ package(default_visibility = ["//visibility:public"])
+ 
+ # Ensure the `requirements.bzl` source can be accessed by stardoc, since users load() from it
+ exports_files(["requirements.bzl"])
++
++py_library(
++    name = "empty",
++    srcs = [],
++)
+ """
+ 
++def _python_version_info(rctx, python_interpreter, info_index):
++    cmd = [
++        python_interpreter,
++        "-c",
++        "from __future__ import print_function; import sys; print(sys.version_info[{}])".format(info_index)
++    ]
++    result = rctx.execute(cmd)
++    if result.stderr or not result.stdout:
++      print("WARNING: Failed to get version info from {}".format(python_interpreter))
++      return None
++    return int(result.stdout.strip())
++
++def _python_version_supported(rctx, python_interpreter):
++    major_version = _python_version_info(rctx, python_interpreter, 0)
++    minor_version = _python_version_info(rctx, python_interpreter, 1)
++    if major_version == None or minor_version == None:
++        print("WARNING: Failed to get Python version of {}".format(python_interpreter))
++        return False
++    if (major_version != 3 or minor_version < 6):
++        print("WARNING: {} is of version {}.{}. This version is unsupported.".format(python_interpreter, major_version, minor_version))
++        return False
++    return True
++
++
+ def _pip_repository_impl(rctx):
+     python_interpreter = _resolve_python_interpreter(rctx)
+ 
+@@ -109,6 +146,11 @@ def _pip_repository_impl(rctx):
+     # We need a BUILD file to load the generated requirements.bzl
+     rctx.file("BUILD.bazel", _BUILD_FILE_CONTENTS)
+ 
++    # Check if python interpreter has minimum required version.
++    if not python_interpreter or not _python_version_supported(rctx, python_interpreter):
++      _generate_stub_requirements_bzl(rctx)
++      return
++
+     pypath = _construct_pypath(rctx)
+ 
+     if rctx.attr.incremental: