diff --git a/src/pytypes/onefuzztypes/_monkeypatch.py b/src/pytypes/onefuzztypes/_monkeypatch.py
new file mode 100644
index 0000000000..fc784c417d
--- /dev/null
+++ b/src/pytypes/onefuzztypes/_monkeypatch.py
@@ -0,0 +1,52 @@
+# TODO: Remove once `smart_union` like support is added to Pydantic
+#
+# Written by @PrettyWood
+# Code from https://github.com/samuelcolvin/pydantic/pull/2092
+#
+# Original project licensed under the MIT License.
+
+from typing import TYPE_CHECKING, Any, Dict, Optional, Union
+
+from pydantic.fields import ModelField
+from pydantic.typing import get_origin
+
+if TYPE_CHECKING:
+    from pydantic.fields import LocStr, ValidateReturn
+    from pydantic.types import ModelOrDc
+
+upstream_validate_singleton = ModelField._validate_singleton
+
+
+# this is a direct port of the functionality from the PR discussed above, though
+# *all* unions are considered "smart" for our purposes.
+def wrap_validate_singleton(
+    self: ModelField,
+    v: Any,
+    values: Dict[str, Any],
+    loc: "LocStr",
+    cls: Optional["ModelOrDc"],
+) -> "ValidateReturn":
+    if self.sub_fields:
+        if get_origin(self.type_) is Union:
+            for field in self.sub_fields:
+                if v.__class__ is field.outer_type_:
+                    return v, None
+            for field in self.sub_fields:
+                try:
+                    if isinstance(v, field.outer_type_):
+                        return v, None
+                except TypeError:
+                    pass
+
+    return upstream_validate_singleton(self, v, values, loc, cls)
+
+
+ModelField._validate_singleton = wrap_validate_singleton  # type: ignore
+
+
+# this should be included in any file that defines a pydantic model that uses a
+# Union and calls to it should be removed when Pydantic's smart union support
+# lands
+def _check_hotfix() -> None:
+    if ModelField._validate_singleton != wrap_validate_singleton:
+        raise Exception("pydantic Union hotfix not applied")
diff --git a/src/pytypes/onefuzztypes/events.py b/src/pytypes/onefuzztypes/events.py
index 85e405ee2f..ef23595990 100644
--- a/src/pytypes/onefuzztypes/events.py
+++ b/src/pytypes/onefuzztypes/events.py
@@ -10,6 +10,7 @@
 
 from pydantic import BaseModel, Field
 
+from ._monkeypatch import _check_hotfix
 from .enums import (
     OS,
     Architecture,
@@ -319,3 +320,6 @@ def parse_event_message(data: Dict[str, Any]) -> EventMessage:
         instance_id=instance_id,
         instance_name=instance_name,
     )
+
+
+_check_hotfix()
diff --git a/src/pytypes/onefuzztypes/job_templates.py b/src/pytypes/onefuzztypes/job_templates.py
index f1dc41b242..c0d32e616c 100644
--- a/src/pytypes/onefuzztypes/job_templates.py
+++ b/src/pytypes/onefuzztypes/job_templates.py
@@ -7,6 +7,7 @@
 
 from pydantic import BaseModel, Field, root_validator, validator
 
+from ._monkeypatch import _check_hotfix
 from .enums import OS, ContainerType, UserFieldOperation, UserFieldType
 from .models import JobConfig, NotificationConfig, TaskConfig, TaskContainers
 from .primitives import File
@@ -184,3 +185,6 @@ class JobTemplateGet(BaseRequest):
 
 class JobTemplateRequestParameters(BaseRequest):
     user_fields: TemplateUserFields
+
+
+_check_hotfix()
diff --git a/src/pytypes/onefuzztypes/models.py b/src/pytypes/onefuzztypes/models.py
index bd22204748..4ad4999639 100644
--- a/src/pytypes/onefuzztypes/models.py
+++ b/src/pytypes/onefuzztypes/models.py
@@ -10,6 +10,7 @@
 from pydantic import BaseModel, Field, root_validator, validator
 from pydantic.dataclasses import dataclass
 
+from ._monkeypatch import _check_hotfix
 from .consts import ONE_HOUR, SEVEN_DAYS
 from .enums import (
     OS,
@@ -842,3 +843,6 @@ class Task(BaseModel):
     events: Optional[List[TaskEventSummary]]
     nodes: Optional[List[NodeAssignment]]
     user_info: Optional[UserInfo]
+
+
+_check_hotfix()
diff --git a/src/pytypes/onefuzztypes/requests.py b/src/pytypes/onefuzztypes/requests.py
index df7c32ebb2..e3c36a9073 100644
--- a/src/pytypes/onefuzztypes/requests.py
+++ b/src/pytypes/onefuzztypes/requests.py
@@ -8,6 +8,7 @@
 
 from pydantic import AnyHttpUrl, BaseModel, Field, root_validator, validator
 
+from ._monkeypatch import _check_hotfix
 from .consts import ONE_HOUR, SEVEN_DAYS
 from .enums import (
     OS,
@@ -250,3 +251,6 @@ class WebhookUpdate(BaseModel):
 class NodeAddSshKey(BaseModel):
     machine_id: UUID
     public_key: str
+
+
+_check_hotfix()