diff --git a/src/backend/core/migrations/0008_alter_item_options_and_more.py b/src/backend/core/migrations/0008_alter_item_options_and_more.py
new file mode 100644
index 00000000..9962e9a9
--- /dev/null
+++ b/src/backend/core/migrations/0008_alter_item_options_and_more.py
@@ -0,0 +1,21 @@
+# Generated by Django 5.2.3 on 2025-06-23 09:22
+
+from django.db import migrations
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('core', '0007_item_hard_deleted_at'),
+    ]
+
+    operations = [
+        migrations.AlterModelOptions(
+            name='item',
+            options={'ordering': ('created_at',), 'verbose_name': 'Item', 'verbose_name_plural': 'Items'},
+        ),
+        migrations.RemoveConstraint(
+            model_name='item',
+            name='check_filename_set_for_files',
+        ),
+    ]
diff --git a/src/backend/core/models.py b/src/backend/core/models.py
index 6aedd60a..ea7766d9 100644
--- a/src/backend/core/models.py
+++ b/src/backend/core/models.py
@@ -556,16 +556,7 @@ class Item(TreeModel, BaseModel):
                     | models.Q(deleted_at=models.F("ancestors_deleted_at"))
                 ),
                 name="check_deleted_at_matches_ancestors_deleted_at_when_set",
-            ),
-            models.CheckConstraint(
-                condition=models.Q(
-                    models.Q(type=ItemTypeChoices.FILE, filename__isnull=False)
-                    | models.Q(
-                        ~models.Q(type=ItemTypeChoices.FILE), filename__isnull=True
-                    )
-                ),
-                name="check_filename_set_for_files",
-            ),
+            )
         ]
         indexes = [
             GistIndex(fields=["path"]),
@@ -576,6 +567,27 @@ class Item(TreeModel, BaseModel):
 
     def save(self, *args, **kwargs):
         """Set the upload state to pending if it's the first save and it's a file"""
+        # Validate filename requirements based on item type
+        if self.type == ItemTypeChoices.FILE:
+            if self.filename is None:
+                raise ValidationError(
+                    {
+                        "filename": ValidationError(
+                            _("Filename is required for files."),
+                            code="item_filename_required_for_files",
+                        )
+                    }
+                )
+        elif self.filename is not None:
+            raise ValidationError(
+                {
+                    "filename": ValidationError(
+                        _("Filename is only allowed for files."),
+                        code="item_filename_only_allowed_for_files",
+                    )
+                }
+            )
+
         if self.created_at is None and self.type == ItemTypeChoices.FILE:
             self.upload_state = ItemUploadStateChoices.PENDING
 
diff --git a/src/backend/core/tests/authentication/test_backends.py b/src/backend/core/tests/authentication/test_backends.py
index 935db218..2d472edb 100644
--- a/src/backend/core/tests/authentication/test_backends.py
+++ b/src/backend/core/tests/authentication/test_backends.py
@@ -500,7 +500,7 @@ def test_authentication_session_tokens(
         status=200,
     )
 
-    with django_assert_num_queries(30):
+    with django_assert_num_queries(27):
         user = klass.authenticate(
             request,
             code="test-code",
diff --git a/src/backend/core/tests/test_models_invitations.py b/src/backend/core/tests/test_models_invitations.py
index 16112890..2a406713 100644
--- a/src/backend/core/tests/test_models_invitations.py
+++ b/src/backend/core/tests/test_models_invitations.py
@@ -143,7 +143,7 @@ def test_models_invitationd_new_user_filter_expired_invitations():
     ).exists()
 
 
-@pytest.mark.parametrize("num_invitations, num_queries", [(0, 27), (1, 31), (20, 31)])
+@pytest.mark.parametrize("num_invitations, num_queries", [(0, 24), (1, 28), (20, 28)])
 def test_models_invitations_new_userd_user_creation_constant_num_queries(
     django_assert_num_queries, num_invitations, num_queries
 ):
diff --git a/src/backend/core/tests/test_models_items.py b/src/backend/core/tests/test_models_items.py
index cb419c90..c405bf8c 100644
--- a/src/backend/core/tests/test_models_items.py
+++ b/src/backend/core/tests/test_models_items.py
@@ -699,7 +699,7 @@ def test_models_items_creating_file_without_filename_should_fail():
         factories.ItemFactory(type=models.ItemTypeChoices.FILE, filename=None)
 
     assert exc_info.value.message_dict == {
-        "__all__": ["Constraint “check_filename_set_for_files” is violated."]
+        "filename": ["Filename is required for files."]
     }
 
 
@@ -717,7 +717,7 @@ def test_models_items_creating_non_file_with_filename_should_fail(item_type):
         factories.ItemFactory(type=item_type, filename="file.txt")
 
     assert exc_info.value.message_dict == {
-        "__all__": ["Constraint “check_filename_set_for_files” is violated."]
+        "filename": ["Filename is only allowed for files."]
     }