diff --git a/CHANGELOG.rst b/CHANGELOG.rst
index c2e3f7d2b3..e056240a97 100644
--- a/CHANGELOG.rst
+++ b/CHANGELOG.rst
@@ -27,6 +27,8 @@ Fixed
 * Fixed schema utils to more reliably handle schemas that define nested arrays (object-array-object-array-string) as discovered in some
   of the ansible installer RBAC tests (see #5684). This includes a test that reproduced the error so we don't hit this again. #5685
 
+* Fixed eventlet monkey patching so more of the unit tests work under pytest. #5689
+
 Added
 ~~~~~
 
diff --git a/conftest.py b/conftest.py
new file mode 100644
index 0000000000..7ca82b787d
--- /dev/null
+++ b/conftest.py
@@ -0,0 +1,25 @@
+# Copyright 2022 The StackStorm 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.
+
+
+def pytest_configure(config):
+    import sys
+
+    sys._called_from_test = True
+
+
+def pytest_unconfigure(config):
+    import sys
+
+    del sys._called_from_test
diff --git a/st2api/tests/unit/controllers/v1/test_action_views.py b/st2api/tests/unit/controllers/v1/test_action_views.py
index bbc76e3760..2f6be710bf 100644
--- a/st2api/tests/unit/controllers/v1/test_action_views.py
+++ b/st2api/tests/unit/controllers/v1/test_action_views.py
@@ -13,6 +13,11 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import mock
 
 from st2common.content import utils as content_utils
diff --git a/st2api/tests/unit/controllers/v1/test_executions_auth.py b/st2api/tests/unit/controllers/v1/test_executions_auth.py
index 9baaf1e0f3..04392b319c 100644
--- a/st2api/tests/unit/controllers/v1/test_executions_auth.py
+++ b/st2api/tests/unit/controllers/v1/test_executions_auth.py
@@ -13,6 +13,11 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import bson
 import copy
 import datetime
diff --git a/st2api/tests/unit/controllers/v1/test_rule_views.py b/st2api/tests/unit/controllers/v1/test_rule_views.py
index 95839c3110..cafc1b7cf2 100644
--- a/st2api/tests/unit/controllers/v1/test_rule_views.py
+++ b/st2api/tests/unit/controllers/v1/test_rule_views.py
@@ -13,6 +13,11 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import six
 
 from st2common.models.system.common import ResourceReference
diff --git a/st2api/tests/unit/controllers/v1/test_runnertypes.py b/st2api/tests/unit/controllers/v1/test_runnertypes.py
index 34c243c545..2e1f47dab7 100644
--- a/st2api/tests/unit/controllers/v1/test_runnertypes.py
+++ b/st2api/tests/unit/controllers/v1/test_runnertypes.py
@@ -13,6 +13,11 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 from st2api.controllers.v1.runnertypes import RunnerTypesController
 
 from st2tests.api import FunctionalTest
diff --git a/st2api/tests/unit/controllers/v1/test_traces.py b/st2api/tests/unit/controllers/v1/test_traces.py
index 79bbdad6ae..9322a6b782 100644
--- a/st2api/tests/unit/controllers/v1/test_traces.py
+++ b/st2api/tests/unit/controllers/v1/test_traces.py
@@ -13,6 +13,11 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 from st2api.controllers.v1.traces import TracesController
 from st2tests.fixturesloader import FixturesLoader
 
diff --git a/st2api/tests/unit/controllers/v1/test_triggertypes.py b/st2api/tests/unit/controllers/v1/test_triggertypes.py
index 414fc34360..2461796e20 100644
--- a/st2api/tests/unit/controllers/v1/test_triggertypes.py
+++ b/st2api/tests/unit/controllers/v1/test_triggertypes.py
@@ -13,6 +13,11 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import six
 
 from st2api.controllers.v1.triggers import TriggerTypeController
diff --git a/st2auth/tests/unit/controllers/v1/test_token.py b/st2auth/tests/unit/controllers/v1/test_token.py
index cd90a6cef1..e56c7e9acb 100644
--- a/st2auth/tests/unit/controllers/v1/test_token.py
+++ b/st2auth/tests/unit/controllers/v1/test_token.py
@@ -13,6 +13,11 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import uuid
 import datetime
 import random
diff --git a/st2common/st2common/models/db/__init__.py b/st2common/st2common/models/db/__init__.py
index d20afb78b2..1cecf3a247 100644
--- a/st2common/st2common/models/db/__init__.py
+++ b/st2common/st2common/models/db/__init__.py
@@ -36,7 +36,11 @@
 # For now, we go with option 2) since it seems to be good enough of a compromise. We detect if we
 # are running inside tests by checking if "nose" module is present - the same logic we already use
 # in a couple of other places (and something which would need to be changed if we switch to pytest).
-if "nose" in sys.modules.keys():
+# For pytest, we set sys._called_from_test in conftest.py
+if "nose" in sys.modules.keys() or hasattr(sys, "_called_from_test"):
+    # pytest can load any test file first, which randomizes where the monkey_patch is needed.
+    # thus mongoengine might already be loaded at this point under pytest!
+    # In that case, we just add the monkey_patch to the top of that test file.
     from st2common.util.monkey_patch import monkey_patch
 
     monkey_patch()
diff --git a/st2common/st2common/util/monkey_patch.py b/st2common/st2common/util/monkey_patch.py
index 598e3e36ee..f187255897 100644
--- a/st2common/st2common/util/monkey_patch.py
+++ b/st2common/st2common/util/monkey_patch.py
@@ -91,7 +91,11 @@ def use_select_poll_workaround(nose_only=True):
     import eventlet
 
     # Work around to get tests to pass with eventlet >= 0.20.0
-    if not nose_only or (nose_only and "nose" in sys.modules.keys()):
+    if not nose_only or (
+        nose_only
+        # sys._called_from_test set in conftest.py for pytest runs
+        and ("nose" in sys.modules.keys() or hasattr(sys, "_called_from_test"))
+    ):
         # Add back blocking poll() to eventlet monkeypatched select
         original_poll = eventlet.patcher.original("select").poll
         select.poll = original_poll
diff --git a/st2common/tests/unit/test_action_param_utils.py b/st2common/tests/unit/test_action_param_utils.py
index 5eecf018dc..8949820f40 100644
--- a/st2common/tests/unit/test_action_param_utils.py
+++ b/st2common/tests/unit/test_action_param_utils.py
@@ -15,6 +15,12 @@
 # limitations under the License.
 
 from __future__ import absolute_import
+
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import copy
 import six
 
diff --git a/st2common/tests/unit/test_db_base.py b/st2common/tests/unit/test_db_base.py
index 6849643243..154fb09708 100644
--- a/st2common/tests/unit/test_db_base.py
+++ b/st2common/tests/unit/test_db_base.py
@@ -14,6 +14,12 @@
 # limitations under the License.
 
 from __future__ import absolute_import
+
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import mongoengine
 
 from st2common.models.db import stormbase
diff --git a/st2common/tests/unit/test_db_fields.py b/st2common/tests/unit/test_db_fields.py
index 4da8400a78..9abd587fb5 100644
--- a/st2common/tests/unit/test_db_fields.py
+++ b/st2common/tests/unit/test_db_fields.py
@@ -23,6 +23,12 @@
 import unittest2
 import orjson
 import zstandard
+
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import mongoengine as me
 
 from st2common.fields import ComplexDateTimeField
diff --git a/st2common/tests/unit/test_param_utils.py b/st2common/tests/unit/test_param_utils.py
index 77c88b1cd3..c5b1959780 100644
--- a/st2common/tests/unit/test_param_utils.py
+++ b/st2common/tests/unit/test_param_utils.py
@@ -16,6 +16,11 @@
 
 from __future__ import absolute_import
 
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import six
 import mock
 
diff --git a/st2common/tests/unit/test_purge_executions.py b/st2common/tests/unit/test_purge_executions.py
index 64ee4cfa67..cb696e08ed 100644
--- a/st2common/tests/unit/test_purge_executions.py
+++ b/st2common/tests/unit/test_purge_executions.py
@@ -14,6 +14,12 @@
 # limitations under the License.
 
 from __future__ import absolute_import
+
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import copy
 from datetime import timedelta
 
diff --git a/st2common/tests/unit/test_purge_trigger_instances.py b/st2common/tests/unit/test_purge_trigger_instances.py
index 515c4040c3..8848ef5f11 100644
--- a/st2common/tests/unit/test_purge_trigger_instances.py
+++ b/st2common/tests/unit/test_purge_trigger_instances.py
@@ -14,6 +14,12 @@
 # limitations under the License.
 
 from __future__ import absolute_import
+
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 from datetime import timedelta
 
 from st2common import log as logging
diff --git a/st2common/tests/unit/test_reference.py b/st2common/tests/unit/test_reference.py
index ced486a867..b0f661ac9a 100644
--- a/st2common/tests/unit/test_reference.py
+++ b/st2common/tests/unit/test_reference.py
@@ -14,6 +14,12 @@
 # limitations under the License.
 
 from __future__ import absolute_import
+
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import copy
 import mock
 import mongoengine
diff --git a/st2common/tests/unit/test_runners_utils.py b/st2common/tests/unit/test_runners_utils.py
index bc6acfcf7e..98f8acd0ea 100644
--- a/st2common/tests/unit/test_runners_utils.py
+++ b/st2common/tests/unit/test_runners_utils.py
@@ -14,6 +14,12 @@
 # limitations under the License.
 
 from __future__ import absolute_import
+
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import mock
 
 from st2common.runners import utils
diff --git a/st2common/tests/unit/test_tags.py b/st2common/tests/unit/test_tags.py
index 6230cedea6..0a5f9f4e5b 100644
--- a/st2common/tests/unit/test_tags.py
+++ b/st2common/tests/unit/test_tags.py
@@ -14,6 +14,12 @@
 # limitations under the License.
 
 from __future__ import absolute_import
+
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import random
 import string
 
diff --git a/st2reactor/tests/unit/test_enforce.py b/st2reactor/tests/unit/test_enforce.py
index 4b282305bd..37317e610a 100644
--- a/st2reactor/tests/unit/test_enforce.py
+++ b/st2reactor/tests/unit/test_enforce.py
@@ -15,6 +15,11 @@
 
 from __future__ import absolute_import
 
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import mock
 
 from st2common.constants import action as action_constants
diff --git a/st2reactor/tests/unit/test_rule_engine.py b/st2reactor/tests/unit/test_rule_engine.py
index 2f70a2a9d7..134eb62ed9 100644
--- a/st2reactor/tests/unit/test_rule_engine.py
+++ b/st2reactor/tests/unit/test_rule_engine.py
@@ -14,6 +14,12 @@
 # limitations under the License.
 
 from __future__ import absolute_import
+
+# pytest: make sure monkey_patching happens before importing mongoengine
+from st2common.util.monkey_patch import monkey_patch
+
+monkey_patch()
+
 import mock
 from mongoengine import NotUniqueError