diff --git a/airflow/dag_processing/manager.py b/airflow/dag_processing/manager.py
index 217e3faa5ead2e..d0876c6e8098fc 100644
--- a/airflow/dag_processing/manager.py
+++ b/airflow/dag_processing/manager.py
@@ -40,7 +40,7 @@
 
 import attrs
 from setproctitle import setproctitle
-from sqlalchemy import and_, delete, select, update
+from sqlalchemy import delete, select, tuple_, update
 from tabulate import tabulate
 from uuid6 import uuid7
 
@@ -756,9 +756,12 @@ def clear_nonexistent_import_errors(self, session=NEW_SESSION):
 
             if self._file_paths:
                 query = query.where(
-                    and_(
-                        ParseImportError.filename.notin_([f.path for f in self._file_paths]),
-                        ParseImportError.bundle_name.notin_([f.bundle_name for f in self._file_paths]),
+                    (
+                        tuple_(
+                            (ParseImportError.filename, ParseImportError.bundle_name).notin_(
+                                [(f.path, f.bundle_name) for f in self._file_paths]
+                            )
+                        ),
                     )
                 )
 
diff --git a/airflow/www/views.py b/airflow/www/views.py
index ee4aff114be94d..c0ce8307dae2be 100644
--- a/airflow/www/views.py
+++ b/airflow/www/views.py
@@ -74,7 +74,7 @@
 from markupsafe import Markup, escape
 from pendulum.datetime import DateTime
 from pendulum.parsing.exceptions import ParserError
-from sqlalchemy import and_, case, desc, func, inspect, or_, select, union_all
+from sqlalchemy import and_, case, desc, func, inspect, or_, select, tuple_, union_all
 from sqlalchemy.exc import IntegrityError
 from sqlalchemy.orm import joinedload
 from wtforms import BooleanField, validators
@@ -1017,11 +1017,12 @@ def index(self):
                 if not can_read_all_dags:
                     # if the user doesn't have access to all DAGs, only display errors from visible DAGs
                     import_errors = import_errors.where(
-                        ParseImportError.filename.in_(
-                            select(DagModel.fileloc).distinct().where(DagModel.dag_id.in_(filter_dag_ids))
-                        ),
-                        ParseImportError.bundle_name.in_(
-                            select(DagModel.bundle_name).distinct().where(DagModel.dag_id.in_(filter_dag_ids))
+                        tuple_(
+                            (ParseImportError.filename, ParseImportError.bundle_name).in_(
+                                select(DagModel.fileloc, DagModel.bundle_name)
+                                .distinct()
+                                .where(DagModel.dag_id.in_(filter_dag_ids))
+                            )
                         ),
                     )