diff --git a/lms/models/assignment.py b/lms/models/assignment.py
index 2992bfdc63..6e23bc5c44 100644
--- a/lms/models/assignment.py
+++ b/lms/models/assignment.py
@@ -1,7 +1,7 @@
 import sqlalchemy as sa
 from sqlalchemy.dialects.postgresql import JSONB
 from sqlalchemy.ext.mutable import MutableDict
-from sqlalchemy.orm import Mapped, mapped_column
+from sqlalchemy.orm import DynamicMapped, Mapped, mapped_column
 
 from lms.db import Base
 from lms.models._mixins import CreatedUpdatedMixin
@@ -78,7 +78,7 @@ class Assignment(CreatedUpdatedMixin, Base):
     deep_linking_uuid: Mapped[str | None] = mapped_column(sa.Unicode, nullable=True)
     """UUID that identifies the deep linking that created this assignment."""
 
-    groupings: Mapped[list[Grouping]] = sa.orm.relationship(
+    groupings: DynamicMapped[Grouping] = sa.orm.relationship(
         secondary="assignment_grouping", viewonly=True, lazy="dynamic"
     )
 
diff --git a/lms/models/oauth2_token.py b/lms/models/oauth2_token.py
index 42148c6739..1d92d8f120 100644
--- a/lms/models/oauth2_token.py
+++ b/lms/models/oauth2_token.py
@@ -4,6 +4,7 @@
 from enum import Enum, unique
 
 import sqlalchemy as sa
+from sqlalchemy.orm import Mapped, mapped_column
 
 from lms.db import Base, varchar_enum
 
@@ -43,7 +44,7 @@ class OAuth2Token(Base):
         sa.UniqueConstraint("user_id", "application_instance_id", "service"),
     )
 
-    id = sa.Column(sa.Integer(), autoincrement=True, primary_key=True)
+    id: Mapped[int] = mapped_column(autoincrement=True, primary_key=True)
 
     #: The LTI user_id of the LMS user who this access token belongs to.
     user_id = sa.Column(sa.UnicodeText(), nullable=False)
@@ -91,11 +92,8 @@ class OAuth2Token(Base):
     #: inserting new rows) then whenever `access_token` and `expires_in`
     #: are updated with new values from the authorization server, `received_at`
     #: should also be updated to the current time.
-    received_at = sa.Column(
-        sa.DateTime,
-        default=datetime.datetime.utcnow,
-        server_default=sa.func.now(),
-        nullable=False,
+    received_at: Mapped[datetime.datetime] = mapped_column(
+        default=datetime.datetime.utcnow, server_default=sa.func.now()
     )
 
     #: The API that this token is used with. In OAuth 2.0 parlance, this
diff --git a/lms/product/plugin/__init__.py b/lms/product/plugin/__init__.py
index 2aa0e73bc6..fe74edd0d5 100644
--- a/lms/product/plugin/__init__.py
+++ b/lms/product/plugin/__init__.py
@@ -1,3 +1,4 @@
+# type: ignore
 from lms.product.plugin.course_copy import CourseCopyPlugin
 from lms.product.plugin.grouping import GroupingPlugin
 from lms.product.plugin.misc import MiscPlugin
diff --git a/lms/product/plugin/course_copy.py b/lms/product/plugin/course_copy.py
index 32b14d4e10..2f293df1b1 100644
--- a/lms/product/plugin/course_copy.py
+++ b/lms/product/plugin/course_copy.py
@@ -1,4 +1,4 @@
-from typing import Callable
+from typing import Any, Callable
 
 from lms.models import File
 from lms.services.exceptions import ExternalRequestError, OAuth2TokenError
@@ -20,7 +20,7 @@ def is_file_in_course(self, course_id, file_id, type_) -> bool:
 
     def find_matching_file_in_course(
         self,
-        store_new_course_files: Callable[[str], None],
+        store_new_course_files: Callable[[str], Any] | Callable[[int], Any],
         file_type: str,
         original_file_id,
         new_course_id,
diff --git a/lms/product/plugin/plugin.py b/lms/product/plugin/plugin.py
index 747bf69106..e4204b0de6 100644
--- a/lms/product/plugin/plugin.py
+++ b/lms/product/plugin/plugin.py
@@ -1,3 +1,4 @@
+# type: ignore
 from dataclasses import dataclass
 from typing import cast
 
diff --git a/lms/product/product.py b/lms/product/product.py
index 28e968edac..213ab8ec0e 100644
--- a/lms/product/product.py
+++ b/lms/product/product.py
@@ -3,7 +3,7 @@
 from dataclasses import InitVar, dataclass
 
 from lms.product.family import Family  # pylint:disable=unused-import
-from lms.product.plugin import PluginConfig, Plugins
+from lms.product.plugin import PluginConfig, Plugins  # type: ignore
 
 
 @dataclass(frozen=True)
diff --git a/lms/services/application_instance.py b/lms/services/application_instance.py
index 31174df43e..28925e9816 100644
--- a/lms/services/application_instance.py
+++ b/lms/services/application_instance.py
@@ -52,14 +52,14 @@ def __init__(self, application_instance: ApplicationInstance):
         )
 
 
-def _email_or_domain_match(columns, email):
+def _email_or_domain_match(columns, email: str):
     """
     Get an SQL comparator for matching emails.
 
     This will match the full email if it contains '@' or interpret the text
     as a domain if not. This will search over all the provided fields.
     """
-    return sa.or_(
+    return sa.or_(  # type: ignore
         (
             sa.func.lower(column) == email.lower()
             if "@" in email
diff --git a/lms/services/digest.py b/lms/services/digest.py
index 94525f0607..60761822f9 100644
--- a/lms/services/digest.py
+++ b/lms/services/digest.py
@@ -400,7 +400,7 @@ def course_infos(self):
 
         for row in self._db.execute(query):
             # SQLAlchemy returns None instead of [].
-            authority_provided_ids = row.authority_provided_ids or []
+            row_authority_provided_ids = row.authority_provided_ids or []
             instructor_h_userids = row.instructor_h_userids or []
 
             self._course_infos.append(
@@ -411,7 +411,8 @@ def course_infos(self):
                     learner_annotations=tuple(
                         annotation
                         for annotation in self.annotations
-                        if annotation.authority_provided_id in authority_provided_ids
+                        if annotation.authority_provided_id
+                        in row_authority_provided_ids
                         and annotation.userid not in instructor_h_userids
                     ),
                 )
diff --git a/lms/services/group_info.py b/lms/services/group_info.py
index e13c162526..15ed8bca06 100644
--- a/lms/services/group_info.py
+++ b/lms/services/group_info.py
@@ -46,7 +46,7 @@ def upsert_group_info(self, grouping: Grouping, params: dict):
         # AI should be many:many, and we reflect that wrongness here.
         group_info.application_instance = grouping.application_instance
 
-        group_info.type = self._GROUPING_TYPES[grouping.type]  # type: ignore
+        group_info.type = self._GROUPING_TYPES[grouping.type]
 
         for field in [
             # Most (all) of these are duplicated elsewhere, we'll keep updating for now
diff --git a/lms/services/moodle.py b/lms/services/moodle.py
index 20b9eb5ab2..6cb77f4fe4 100644
--- a/lms/services/moodle.py
+++ b/lms/services/moodle.py
@@ -255,7 +255,7 @@ def _construct_file_tree(course_id, files):
                         "children": [],
                     }
                     folders[component] = new_folder
-                    current_node["children"].append(new_folder)
+                    current_node["children"].append(new_folder)  # type: ignore
                 current_node = folders[component]
 
             file_node = {
@@ -266,7 +266,7 @@ def _construct_file_tree(course_id, files):
                 "lms_id": file_data["url"],
                 "updated_at": file_data["updated_at"],
             }
-            current_node["children"].append(file_node)
+            current_node["children"].append(file_node)  # type: ignore
 
         return root["children"]
 
diff --git a/lms/validation/__init__.py b/lms/validation/__init__.py
index 48fe3d2cfe..1ee9190f5f 100644
--- a/lms/validation/__init__.py
+++ b/lms/validation/__init__.py
@@ -97,5 +97,5 @@ def wrapper_view(context, request):
 
 
 def includeme(config):
-    _validated_view.options = ["schema"]
+    _validated_view.options = ["schema"]  # type: ignore
     config.add_view_deriver(_validated_view)
diff --git a/lms/views/admin/assignment.py b/lms/views/admin/assignment.py
index 41fa0a0b6e..613c311fb3 100644
--- a/lms/views/admin/assignment.py
+++ b/lms/views/admin/assignment.py
@@ -55,7 +55,7 @@ def assignment_dashboard(self):
                 "dashboard.assignment",
                 public_id=assignment.groupings[
                     0
-                ].application_instance.organization.public_id,
+                ].application_instance.organization.public_id,  # type: ignore
                 assignment_id=assignment.id,
             ),
         )
diff --git a/lms/views/admin/organization.py b/lms/views/admin/organization.py
index aeb66e9e22..45c3b5c228 100644
--- a/lms/views/admin/organization.py
+++ b/lms/views/admin/organization.py
@@ -50,7 +50,7 @@ def __init__(self, request) -> None:
         self.organization_service: OrganizationService = request.find_service(
             OrganizationService
         )
-        self.organization_usage_report_service: OrganizationService = (
+        self.organization_usage_report_service: OrganizationUsageReportService = (
             request.find_service(OrganizationUsageReportService)
         )
 
@@ -155,6 +155,7 @@ def toggle_organization_enabled(self):
         request_org_id = self.request.matchdict["id_"]
         for org_id in self.organization_service.get_hierarchy_ids(request_org_id):
             org = self.organization_service.get_by_id(org_id)
+            assert org, "Organization {org_id} not found"
             self.organization_service.update_organization(
                 org, enabled=self.request.params.get("enabled", "") == "on"
             )
diff --git a/lms/views/api/blackboard/files.py b/lms/views/api/blackboard/files.py
index e91b4698e8..a683ec7a1f 100644
--- a/lms/views/api/blackboard/files.py
+++ b/lms/views/api/blackboard/files.py
@@ -75,9 +75,9 @@ def via_url(self):
         )
 
         document_url = self.request.params["document_url"]
-        file_id = course.get_mapped_file_id(
-            DOCUMENT_URL_REGEX.search(document_url)["file_id"]  # type: ignore
-        )
+        document_url_match = DOCUMENT_URL_REGEX.search(document_url)
+        assert document_url_match
+        file_id = course.get_mapped_file_id(document_url_match["file_id"])
         try:
             if self.request.lti_user.is_instructor:
                 if not self.course_copy_plugin.is_file_in_course(course_id, file_id):
diff --git a/lms/views/api/canvas/authorize.py b/lms/views/api/canvas/authorize.py
index a4e1ff0324..989b58dcc0 100644
--- a/lms/views/api/canvas/authorize.py
+++ b/lms/views/api/canvas/authorize.py
@@ -152,7 +152,7 @@ def oauth2_redirect_error(request):
         )
 
     if error_description := request.params.get("error_description"):
-        kwargs["error_details"] = {"error_description": error_description}
+        kwargs["error_details"] = {"error_description": error_description}  # type: ignore
 
     request.context.js_config.enable_oauth2_redirect_error_mode(**kwargs)
 
diff --git a/lms/views/api/canvas/files.py b/lms/views/api/canvas/files.py
index 60bd42e26e..5aaaecfec2 100644
--- a/lms/views/api/canvas/files.py
+++ b/lms/views/api/canvas/files.py
@@ -46,6 +46,7 @@ def via_url(self):
         )
 
         document_url_match = DOCUMENT_URL_REGEX.search(assignment.document_url)
+        assert document_url_match
         public_url = self.canvas.public_url_for_file(
             assignment,
             document_url_match["file_id"],
diff --git a/lms/views/api/canvas/pages.py b/lms/views/api/canvas/pages.py
index ac11592a46..59e7017076 100644
--- a/lms/views/api/canvas/pages.py
+++ b/lms/views/api/canvas/pages.py
@@ -168,6 +168,7 @@ def proxy(self):
     @staticmethod
     def _parse_document_url(document_url):
         document_url_match = DOCUMENT_URL_REGEX.search(document_url)
+        assert document_url_match
         course_id = document_url_match["course_id"]
         page_id = document_url_match["page_id"]
 
diff --git a/lms/views/api/d2l/authorize.py b/lms/views/api/d2l/authorize.py
index 86d1d9d2da..04ffd27819 100644
--- a/lms/views/api/d2l/authorize.py
+++ b/lms/views/api/d2l/authorize.py
@@ -17,7 +17,7 @@
     permission=Permissions.API,
 )
 def authorize(request):
-    scopes = []
+    scopes: list[str] = []
 
     if request.product.settings.files_enabled:
         scopes += FILES_SCOPES
diff --git a/lms/views/api/d2l/files.py b/lms/views/api/d2l/files.py
index c74e1cffbf..8138f72cf5 100644
--- a/lms/views/api/d2l/files.py
+++ b/lms/views/api/d2l/files.py
@@ -40,9 +40,9 @@ def via_url(_context, request):
         course_id, raise_on_missing=True
     )
 
-    file_id = course.get_mapped_file_id(
-        DOCUMENT_URL_REGEX.search(document_url)["file_id"]
-    )
+    document_url_match = DOCUMENT_URL_REGEX.search(document_url)
+    assert document_url_match
+    file_id = course.get_mapped_file_id(document_url_match["file_id"])
     try:
         if request.lti_user.is_instructor:
             if not course_copy_plugin.is_file_in_course(course_id, file_id):
diff --git a/lms/views/api/moodle/files.py b/lms/views/api/moodle/files.py
index 5dc89f0450..c07fcddaad 100644
--- a/lms/views/api/moodle/files.py
+++ b/lms/views/api/moodle/files.py
@@ -44,8 +44,10 @@ def via_url(_context, request):
     )
 
     document_url = request.params["document_url"]
-    document_course_id = DOCUMENT_URL_REGEX.search(document_url)["course_id"]
-    document_file_id = DOCUMENT_URL_REGEX.search(document_url)["url"]
+    document_url_match = DOCUMENT_URL_REGEX.search(document_url)
+    assert document_url_match
+    document_course_id = document_url_match["course_id"]
+    document_file_id = document_url_match["url"]
     effective_file_id = _effective_file_id(
         course_copy_plugin, course, document_url, document_course_id, document_file_id
     )
diff --git a/lms/views/api/moodle/pages.py b/lms/views/api/moodle/pages.py
index 9198c39390..979343e2c8 100644
--- a/lms/views/api/moodle/pages.py
+++ b/lms/views/api/moodle/pages.py
@@ -113,6 +113,7 @@ def proxy(self):
     @staticmethod
     def _parse_document_url(document_url):
         document_url_match = DOCUMENT_URL_REGEX.search(document_url)
+        assert document_url_match
         course_id = document_url_match["course_id"]
         page_id = document_url_match["page_id"]
 
diff --git a/lms/views/lti/basic_launch.py b/lms/views/lti/basic_launch.py
index d87b1e941a..f157870fe0 100644
--- a/lms/views/lti/basic_launch.py
+++ b/lms/views/lti/basic_launch.py
@@ -266,7 +266,7 @@ def _configure_assignment(self, assignment):
         )
 
     def _configure_js_for_file_picker(
-        self, assignment: Assignment, route: str = "configure_assignment"
+        self, assignment: Assignment | None, route: str = "configure_assignment"
     ) -> dict:
         """
         Show the file-picker for the user to choose a document.
diff --git a/pyproject.toml b/pyproject.toml
index 35e3ff3b3c..4c45f84b40 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -225,7 +225,7 @@ python_version = 3.11
 warn_unused_configs = true
 warn_redundant_casts = true
 warn_unused_ignores = true
-
+check_untyped_defs = true
 
 disable_error_code = [
     "import-untyped",