diff --git a/src/pretix/base/services/orders.py b/src/pretix/base/services/orders.py
index d15e9ce246..09c5505f19 100644
--- a/src/pretix/base/services/orders.py
+++ b/src/pretix/base/services/orders.py
@@ -984,7 +984,7 @@ def send_download_reminders(sender, **kwargs):
             continue
 
         reminder_date = (o.first_date - timedelta(days=days)).replace(hour=0, minute=0, second=0, microsecond=0)
-        if now() < reminder_date:
+        if now() < reminder_date or o.datetime > reminder_date:
             continue
 
         with transaction.atomic():
diff --git a/src/tests/base/test_orders.py b/src/tests/base/test_orders.py
index d8546b89e7..82121efc7d 100644
--- a/src/tests/base/test_orders.py
+++ b/src/tests/base/test_orders.py
@@ -434,7 +434,7 @@ class DownloadReminderTests(TestCase):
             self.order = Order.objects.create(
                 code='FOO', event=self.event, email='dummy@dummy.test',
                 status=Order.STATUS_PAID, locale='en',
-                datetime=now() - timedelta(hours=4),
+                datetime=now() - timedelta(days=4),
                 expires=now() - timedelta(hours=4) + timedelta(days=10),
                 total=Decimal('46.00'),
             )
@@ -533,6 +533,14 @@ class DownloadReminderTests(TestCase):
         send_download_reminders(sender=self.event)
         assert len(djmail.outbox) == 0
 
+    @classscope(attr='o')
+    def test_not_sent_after_reminder_date(self):
+        self.order.datetime = self.event.date_from - timedelta(days=1)
+        self.order.save()
+        self.event.settings.mail_days_download_reminder = 2
+        send_download_reminders(sender=self.event)
+        assert len(djmail.outbox) == 0
+
 
 class OrderCancelTests(TestCase):
     def setUp(self):