diff --git a/core/files/migrations/0003_ensure_creation_date.py b/core/files/migrations/0003_ensure_creation_date.py
new file mode 100644
index 0000000..63e5760
--- /dev/null
+++ b/core/files/migrations/0003_ensure_creation_date.py
@@ -0,0 +1,24 @@
+# Generated by Django 4.2.7 on 2024-11-21 22:40
+
+from django.db import migrations
+
+
+class Migration(migrations.Migration):
+    dependencies = [
+        ('files', '0002_alter_file_file'),
+    ]
+
+    def set_creation_date(apps, schema_editor):
+        File = apps.get_model('files', 'File')
+        for file in File.objects.all():
+            if file.created_at is None:
+                if not file.item.created_at is None:
+                    file.created_at = file.item.created_at
+                else:
+                    file.created_at = max(File.objects.filter(
+                        id__lt=file.id, created_at__isnull=False).values_list('created_at', flat=True))
+                file.save()
+
+    operations = [
+        migrations.RunPython(set_creation_date),
+    ]
diff --git a/core/inventory/tests/v2/test_items.py b/core/inventory/tests/v2/test_items.py
index 59a5a4e..d289a70 100644
--- a/core/inventory/tests/v2/test_items.py
+++ b/core/inventory/tests/v2/test_items.py
@@ -56,6 +56,23 @@ class ItemTestCase(TestCase):
         self.assertEqual(response.json()[0]['event'], self.event.slug)
         self.assertEqual(len(response.json()[0]['related_issues']), 0)
 
+    def test_members_with_two_file(self):
+        import base64
+        item = Item.objects.create(container=self.box, event=self.event, description='1')
+        file1 = File.objects.create(item=item, data="data:text/plain;base64," + base64.b64encode(b"foo").decode('utf-8'))
+        file2 = File.objects.create(item=item, data="data:text/plain;base64," + base64.b64encode(b"bar").decode('utf-8'))
+        response = self.client.get(f'/api/2/{self.event.slug}/item/')
+        self.assertEqual(response.status_code, 200)
+        self.assertEqual(len(response.json()), 1)
+        self.assertEqual(response.json()[0]['id'], item.id)
+        self.assertEqual(response.json()[0]['description'], '1')
+        self.assertEqual(response.json()[0]['box'], 'BOX')
+        self.assertEqual(response.json()[0]['cid'], self.box.id)
+        self.assertEqual(response.json()[0]['file'], file2.hash)
+        self.assertEqual(response.json()[0]['returned'], False)
+        self.assertEqual(response.json()[0]['event'], self.event.slug)
+        self.assertEqual(len(response.json()[0]['related_issues']), 0)
+
     def test_multi_members(self):
         Item.objects.create(container=self.box, event=self.event, description='1')
         Item.objects.create(container=self.box, event=self.event, description='2')