diff --git a/common/djangoapps/student/models/course_enrollment.py b/common/djangoapps/student/models/course_enrollment.py
index 750ac66e38c0..6d32ffca4149 100644
--- a/common/djangoapps/student/models/course_enrollment.py
+++ b/common/djangoapps/student/models/course_enrollment.py
@@ -717,6 +717,8 @@ def enroll(cls, user, course_key, mode=None, check_access=False, can_upgrade=Fal
         Also emits relevant events for analytics purposes.
         """
         try:
+            # .. filter_implemented_name: CourseEnrollmentStarted
+            # .. filter_type: org.openedx.learning.course.enrollment.started.v1
             user, course_key, mode = CourseEnrollmentStarted.run_filter(
                 user=user, course_key=course_key, mode=mode,
             )
diff --git a/common/djangoapps/student/views/management.py b/common/djangoapps/student/views/management.py
index b06cac7b7e50..02940da78f3b 100644
--- a/common/djangoapps/student/views/management.py
+++ b/common/djangoapps/student/views/management.py
@@ -70,6 +70,7 @@
 from common.djangoapps.student.models import (  # lint-amnesty, pylint: disable=unused-import
     AccountRecovery,
     CourseEnrollment,
+    EnrollmentNotAllowed,
     PendingEmailChange,  # unimport:skip
     PendingSecondaryEmailChange,
     Registration,
@@ -422,6 +423,8 @@ def change_enrollment(request, check_access=True):
                 enroll_mode = CourseMode.auto_enroll_mode(course_id, available_modes)
                 if enroll_mode:
                     CourseEnrollment.enroll(user, course_id, check_access=check_access, mode=enroll_mode)
+            except EnrollmentNotAllowed as exc:
+                return HttpResponseBadRequest(str(exc))
             except Exception:  # pylint: disable=broad-except
                 return HttpResponseBadRequest(_("Could not enroll"))
 
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
diff --git a/requirements/constraints.txt b/requirements/constraints.txt
index 4258dd8f15f1..fcea298aedae 100644
--- a/requirements/constraints.txt
+++ b/requirements/constraints.txt
@@ -61,11 +61,13 @@ django-webpack-loader==0.7.0
 djangorestframework<3.15.0
 
 # Date: 2024-07-19
-# Generally speaking, the major version of django-stubs should match the major version of django.
-# Specifically, we need to perpetually constrain django-stubs to a compatible version based on:
+# Generally speaking, the major version of django-stubs must either match the major version
+# of django, or exceed it by 1. So, we will need to perpetually constrain django-stubs and
+# update it as we perform django upgrades. For more details, see:
 # https://github.com/typeddjango/django-stubs?tab=readme-ov-file#version-compatibility
+# including the note on "Partial Support".
 # Issue: https://github.com/openedx/edx-platform/issues/35275
-django-stubs<5
+django-stubs<6
 
 # Date: 2024-07-23
 # django-storages==1.14.4 breaks course imports
@@ -112,12 +114,6 @@ markdown<3.4.0
 # Issue for unpinning: https://github.com/openedx/edx-platform/issues/35270
 moto<5.0
 
-# Date: 2024-10-16
-# MyPY 1.12.0 fails on all PRs with the following error:
-# openedx/core/djangoapps/content_libraries/api.py:732: error: INTERNAL ERROR
-# Issue for unpinning: https://github.com/openedx/edx-platform/issues/35667
-mypy<1.12.0
-
 # Date: 2024-07-16
 # We need to upgrade the version of elasticsearch to atleast 7.15 before we can upgrade to Numpy 2.0.0
 # Otherwise we see a failure while running the following command:
diff --git a/requirements/edx/base.txt b/requirements/edx/base.txt
index 92a33194504b..81043c8da103 100644
--- a/requirements/edx/base.txt
+++ b/requirements/edx/base.txt
@@ -705,7 +705,7 @@ lazy==1.6
     #   xblock
 loremipsum==1.0.5
     # via ora2
-lti-consumer-xblock==9.12.1
+lti-consumer-xblock==9.13.0
     # via -r requirements/edx/kernel.in
 lxml[html-clean,html_clean]==5.3.0
     # via
@@ -942,6 +942,7 @@ pyjwt[crypto]==2.10.1
     #   edx-proctoring
     #   edx-rest-api-client
     #   firebase-admin
+    #   lti-consumer-xblock
     #   pylti1p3
     #   snowflake-connector-python
     #   social-auth-core
diff --git a/requirements/edx/development.txt b/requirements/edx/development.txt
index 72522de5db01..c8959e777dda 100644
--- a/requirements/edx/development.txt
+++ b/requirements/edx/development.txt
@@ -76,6 +76,7 @@ asgiref==3.8.1
     #   django
     #   django-cors-headers
     #   django-countries
+    #   django-stubs
 asn1crypto==1.5.1
     # via
     #   -r requirements/edx/doc.txt
@@ -577,7 +578,7 @@ django-storages==1.14.3
     #   -r requirements/edx/doc.txt
     #   -r requirements/edx/testing.txt
     #   edxval
-django-stubs==4.2.7
+django-stubs==5.1.1
     # via
     #   -c requirements/edx/../constraints.txt
     #   -r requirements/edx/development.in
@@ -625,7 +626,7 @@ djangorestframework==3.14.0
     #   openedx-learning
     #   ora2
     #   super-csv
-djangorestframework-stubs==3.14.5
+djangorestframework-stubs==3.15.2
     # via -r requirements/edx/development.in
 djangorestframework-xml==2.0.0
     # via
@@ -1188,7 +1189,7 @@ loremipsum==1.0.5
     #   -r requirements/edx/doc.txt
     #   -r requirements/edx/testing.txt
     #   ora2
-lti-consumer-xblock==9.12.1
+lti-consumer-xblock==9.13.0
     # via
     #   -r requirements/edx/doc.txt
     #   -r requirements/edx/testing.txt
@@ -1292,10 +1293,8 @@ multidict==6.1.0
     #   -r requirements/edx/testing.txt
     #   aiohttp
     #   yarl
-mypy==1.11.2
-    # via
-    #   -c requirements/edx/../constraints.txt
-    #   -r requirements/edx/development.in
+mypy==1.14.1
+    # via -r requirements/edx/development.in
 mypy-extensions==1.0.0
     # via mypy
 mysqlclient==2.2.6
@@ -1611,6 +1610,7 @@ pyjwt[crypto]==2.10.1
     #   edx-proctoring
     #   edx-rest-api-client
     #   firebase-admin
+    #   lti-consumer-xblock
     #   pylti1p3
     #   snowflake-connector-python
     #   social-auth-core
@@ -2119,8 +2119,6 @@ tqdm==4.67.1
     #   -r requirements/edx/testing.txt
     #   nltk
     #   openai
-types-pytz==2024.2.0.20241221
-    # via django-stubs
 types-pyyaml==6.0.12.20241230
     # via
     #   django-stubs
diff --git a/requirements/edx/doc.txt b/requirements/edx/doc.txt
index cf590ac75130..1e329aefbd0f 100644
--- a/requirements/edx/doc.txt
+++ b/requirements/edx/doc.txt
@@ -860,7 +860,7 @@ loremipsum==1.0.5
     # via
     #   -r requirements/edx/base.txt
     #   ora2
-lti-consumer-xblock==9.12.1
+lti-consumer-xblock==9.13.0
     # via -r requirements/edx/base.txt
 lxml[html-clean]==5.3.0
     # via
@@ -1158,6 +1158,7 @@ pyjwt[crypto]==2.10.1
     #   edx-proctoring
     #   edx-rest-api-client
     #   firebase-admin
+    #   lti-consumer-xblock
     #   pylti1p3
     #   snowflake-connector-python
     #   social-auth-core
diff --git a/requirements/edx/testing.txt b/requirements/edx/testing.txt
index d4ee1a6c4f65..8c68cfa387d1 100644
--- a/requirements/edx/testing.txt
+++ b/requirements/edx/testing.txt
@@ -903,7 +903,7 @@ loremipsum==1.0.5
     # via
     #   -r requirements/edx/base.txt
     #   ora2
-lti-consumer-xblock==9.12.1
+lti-consumer-xblock==9.13.0
     # via -r requirements/edx/base.txt
 lxml[html-clean]==5.3.0
     # via
@@ -1222,6 +1222,7 @@ pyjwt[crypto]==2.10.1
     #   edx-proctoring
     #   edx-rest-api-client
     #   firebase-admin
+    #   lti-consumer-xblock
     #   pylti1p3
     #   snowflake-connector-python
     #   social-auth-core