diff --git a/openedx/core/djangoapps/content_libraries/views.py b/openedx/core/djangoapps/content_libraries/views.py
index c8c91d50331f..4c14651c7961 100644
--- a/openedx/core/djangoapps/content_libraries/views.py
+++ b/openedx/core/djangoapps/content_libraries/views.py
@@ -122,6 +122,7 @@
 from openedx.core.lib.api.view_utils import view_auth_classes
 from openedx.core.djangoapps.safe_sessions.middleware import mark_user_change_as_expected
 from openedx.core.djangoapps.xblock import api as xblock_api
+from openedx.core.types.http import RestRequest
 
 from .models import ContentLibrary, LtiGradedResource, LtiProfile
 
@@ -667,7 +668,7 @@ class LibraryBlockCollectionsView(APIView):
     View to set collections for a component.
     """
     @convert_exceptions
-    def patch(self, request, usage_key_str) -> Response:
+    def patch(self, request: RestRequest, usage_key_str) -> Response:
         """
         Sets Collections for a Component.
 
@@ -688,7 +689,7 @@ def patch(self, request, usage_key_str) -> Response:
             library_key=key.lib_key,
             component=component,
             collection_keys=collection_keys,
-            created_by=self.request.user.id,
+            created_by=request.user.id,
             content_library=content_library,
         )
 
diff --git a/openedx/core/djangoapps/content_libraries/views_collections.py b/openedx/core/djangoapps/content_libraries/views_collections.py
index b6c1c999ba94..21c4b12dd3da 100644
--- a/openedx/core/djangoapps/content_libraries/views_collections.py
+++ b/openedx/core/djangoapps/content_libraries/views_collections.py
@@ -25,6 +25,7 @@
     ContentLibraryCollectionComponentsUpdateSerializer,
     ContentLibraryCollectionUpdateSerializer,
 )
+from openedx.core.types.http import RestRequest
 
 
 class LibraryCollectionsView(ModelViewSet):
@@ -89,7 +90,7 @@ def get_object(self) -> Collection:
         return collection
 
     @convert_exceptions
-    def retrieve(self, request, *args, **kwargs) -> Response:
+    def retrieve(self, request: RestRequest, *args, **kwargs) -> Response:
         """
         Retrieve the Content Library Collection
         """
@@ -97,7 +98,7 @@ def retrieve(self, request, *args, **kwargs) -> Response:
         return super().retrieve(request, *args, **kwargs)
 
     @convert_exceptions
-    def list(self, request, *args, **kwargs) -> Response:
+    def list(self, request: RestRequest, *args, **kwargs) -> Response:
         """
         List Collections that belong to Content Library
         """
@@ -105,7 +106,7 @@ def list(self, request, *args, **kwargs) -> Response:
         return super().list(request, *args, **kwargs)
 
     @convert_exceptions
-    def create(self, request, *args, **kwargs) -> Response:
+    def create(self, request: RestRequest, *args, **kwargs) -> Response:
         """
         Create a Collection that belongs to a Content Library
         """
@@ -139,7 +140,7 @@ def create(self, request, *args, **kwargs) -> Response:
         return Response(serializer.data)
 
     @convert_exceptions
-    def partial_update(self, request, *args, **kwargs) -> Response:
+    def partial_update(self, request: RestRequest, *args, **kwargs) -> Response:
         """
         Update a Collection that belongs to a Content Library
         """
@@ -161,7 +162,7 @@ def partial_update(self, request, *args, **kwargs) -> Response:
         return Response(serializer.data)
 
     @convert_exceptions
-    def destroy(self, request, *args, **kwargs) -> Response:
+    def destroy(self, request: RestRequest, *args, **kwargs) -> Response:
         """
         Soft-deletes a Collection that belongs to a Content Library
         """
@@ -176,7 +177,7 @@ def destroy(self, request, *args, **kwargs) -> Response:
 
     @convert_exceptions
     @action(detail=True, methods=['post'], url_path='restore', url_name='collection-restore')
-    def restore(self, request, *args, **kwargs) -> Response:
+    def restore(self, request: RestRequest, *args, **kwargs) -> Response:
         """
         Restores a soft-deleted Collection that belongs to a Content Library
         """
@@ -191,7 +192,7 @@ def restore(self, request, *args, **kwargs) -> Response:
 
     @convert_exceptions
     @action(detail=True, methods=['delete', 'patch'], url_path='components', url_name='components-update')
-    def update_components(self, request, *args, **kwargs) -> Response:
+    def update_components(self, request: RestRequest, *args, **kwargs) -> Response:
         """
         Adds (PATCH) or removes (DELETE) Components to/from a Collection.
 
@@ -209,7 +210,7 @@ def update_components(self, request, *args, **kwargs) -> Response:
             content_library=content_library,
             collection_key=collection_key,
             usage_keys=usage_keys,
-            created_by=self.request.user.id,
+            created_by=request.user.id,
             remove=(request.method == "DELETE"),
         )
 
diff --git a/openedx/core/djangoapps/content_staging/api.py b/openedx/core/djangoapps/content_staging/api.py
index f0432922dcb0..5f85d701faa5 100644
--- a/openedx/core/djangoapps/content_staging/api.py
+++ b/openedx/core/djangoapps/content_staging/api.py
@@ -66,7 +66,7 @@ def save_xblock_to_user_clipboard(block: XBlock, user_id: int, version_num: int
             olx=block_data.olx_str,
             display_name=block_metadata_utils.display_name_with_default(block),
             suggested_url_name=usage_key.block_id,
-            tags=block_data.tags,
+            tags=block_data.tags or {},
             version_num=(version_num or 0),
         )
         (clipboard, _created) = _UserClipboard.objects.update_or_create(user_id=user_id, defaults={
@@ -209,7 +209,7 @@ def _user_clipboard_model_to_data(clipboard: _UserClipboard) -> UserClipboardDat
             status=content.status,
             block_type=content.block_type,
             display_name=content.display_name,
-            tags=content.tags,
+            tags=content.tags or {},
             version_num=content.version_num,
         ),
         source_usage_key=clipboard.source_usage_key,
diff --git a/openedx/core/djangoapps/content_staging/models.py b/openedx/core/djangoapps/content_staging/models.py
index 2eab7954e826..5e007bc4485a 100644
--- a/openedx/core/djangoapps/content_staging/models.py
+++ b/openedx/core/djangoapps/content_staging/models.py
@@ -67,7 +67,9 @@ class Meta:
     version_num = models.PositiveIntegerField(default=0)
 
     # Tags applied to the original source block(s) will be copied to the new block(s) on paste.
-    tags = models.JSONField(null=True, help_text=_("Content tags applied to these blocks"))
+    tags: models.JSONField[dict | None, dict | None] = models.JSONField(
+        null=True, help_text=_("Content tags applied to these blocks")
+    )
 
     @property
     def olx_filename(self) -> str:
diff --git a/openedx/core/djangoapps/content_tagging/rest_api/v1/views.py b/openedx/core/djangoapps/content_tagging/rest_api/v1/views.py
index c2f79ef677db..615406ffccc5 100644
--- a/openedx/core/djangoapps/content_tagging/rest_api/v1/views.py
+++ b/openedx/core/djangoapps/content_tagging/rest_api/v1/views.py
@@ -10,7 +10,6 @@
 from rest_framework import status
 from rest_framework.decorators import action
 from rest_framework.exceptions import PermissionDenied, ValidationError
-from rest_framework.request import Request
 from rest_framework.response import Response
 from rest_framework.views import APIView
 from openedx_events.content_authoring.data import ContentObjectData, ContentObjectChangedData
@@ -19,6 +18,8 @@
     CONTENT_OBJECT_TAGS_CHANGED,
 )
 
+from openedx.core.types.http import RestRequest
+
 from ...auth import has_view_object_tags_access
 from ...api import (
     create_taxonomy,
@@ -99,7 +100,7 @@ def perform_create(self, serializer):
         serializer.instance = create_taxonomy(**serializer.validated_data, orgs=user_admin_orgs)
 
     @action(detail=False, url_path="import", methods=["post"])
-    def create_import(self, request: Request, **kwargs) -> Response:  # type: ignore
+    def create_import(self, request: RestRequest, **kwargs) -> Response:  # type: ignore
         """
         Creates a new taxonomy with the given orgs and imports the tags from the uploaded file.
         """
@@ -183,7 +184,7 @@ class ObjectTagExportView(APIView):
     """"
     View to export a CSV with all children and tags for a given course/context.
     """
-    def get(self, request: Request, **kwargs) -> StreamingHttpResponse:
+    def get(self, request: RestRequest, **kwargs) -> StreamingHttpResponse:
         """
         Export a CSV with all children and tags for a given course/context.
         """
diff --git a/openedx/core/types/http.py b/openedx/core/types/http.py
new file mode 100644
index 000000000000..2896256a107a
--- /dev/null
+++ b/openedx/core/types/http.py
@@ -0,0 +1,45 @@
+"""
+Typing utilities for the HTTP requests, responses, etc.
+
+Includes utilties to work with both vanilla django as well as djangorestframework.
+"""
+from __future__ import annotations
+
+import django.contrib.auth.models  # pylint: disable=imported-auth-user
+import django.http
+import rest_framework.request
+
+import openedx.core.types.user
+from openedx.core.types.meta import type_annotation_only
+
+
+@type_annotation_only
+class HttpRequest(django.http.HttpRequest):
+    """
+    A request which either has a concrete User (from django.contrib.auth) or is anonymous.
+    """
+    user: openedx.core.types.User
+
+
+@type_annotation_only
+class AuthenticatedHttpRequest(HttpRequest):
+    """
+    A request which is guaranteed to have a concrete User (from django.contrib.auth).
+    """
+    user: django.contrib.auth.models.User
+
+
+@type_annotation_only
+class RestRequest(rest_framework.request.Request):
+    """
+    Same as HttpRequest, but extended for rest_framework views.
+    """
+    user: openedx.core.types.User
+
+
+@type_annotation_only
+class AuthenticatedRestRequest(RestRequest):
+    """
+    Same as AuthenticatedHttpRequest, but extended for rest_framework views.
+    """
+    user: django.contrib.auth.models.User
diff --git a/openedx/core/types/meta.py b/openedx/core/types/meta.py
new file mode 100644
index 000000000000..39162b05b879
--- /dev/null
+++ b/openedx/core/types/meta.py
@@ -0,0 +1,37 @@
+"""
+Typing utilities for use on other typing utilities.
+"""
+from __future__ import annotations
+
+import typing as t
+
+
+def type_annotation_only(cls: type) -> type:
+    """
+    Decorates class which should only be used in type annotations.
+
+    This is useful when you want to enhance an existing 3rd-party concrete class with
+    type annotations for its members, but don't want the enhanced class to ever actually
+    be instantiated. For examples, see openedx.core.types.http.
+    """
+    if t.TYPE_CHECKING:
+        return cls
+    return _forbid_init(cls)
+
+
+def _forbid_init(forbidden: type) -> type:
+    """
+    Return a class which refuses to be instantiated.
+    """
+    class _ForbidInit:
+        """
+        The resulting class.
+        """
+        def __init__(self, *args, **kwargs):
+            raise NotImplementedError(
+                f"Class {forbidden.__module__}:{forbidden.__name__} "
+                "cannot be instantiated. You may use it as a type annotation, but objects "
+                "can only be created from its concrete superclasses."
+            )
+
+    return _ForbidInit
diff --git a/openedx/core/types/user.py b/openedx/core/types/user.py
index 95b1fec607fc..9eb63edba358 100644
--- a/openedx/core/types/user.py
+++ b/openedx/core/types/user.py
@@ -1,8 +1,10 @@
 """
 Typing utilities for the User models.
 """
-from typing import Union
+from __future__ import annotations
+
+import typing as t
 
 import django.contrib.auth.models
 
-User = Union[django.contrib.auth.models.User, django.contrib.auth.models.AnonymousUser]
+User: t.TypeAlias = django.contrib.auth.models.User | django.contrib.auth.models.AnonymousUser