diff --git a/src/pretix/plugins/sendmail/models.py b/src/pretix/plugins/sendmail/models.py
index ce2c2ac644..d6d0626d16 100644
--- a/src/pretix/plugins/sendmail/models.py
+++ b/src/pretix/plugins/sendmail/models.py
@@ -41,11 +41,13 @@ class ScheduledMail(models.Model):
     STATE_SCHEDULED = 'scheduled'
     STATE_FAILED = 'failed'
     STATE_COMPLETED = 'completed'
+    STATE_MISSED = 'missed'
 
     STATE_CHOICES = [
         (STATE_SCHEDULED, STATE_SCHEDULED),
         (STATE_FAILED, STATE_FAILED),
         (STATE_COMPLETED, STATE_COMPLETED),
+        (STATE_MISSED, STATE_MISSED),
     ]
 
     id = models.BigAutoField(primary_key=True)
diff --git a/src/pretix/plugins/sendmail/signals.py b/src/pretix/plugins/sendmail/signals.py
index 23452d6d76..33c0aeaf5b 100644
--- a/src/pretix/plugins/sendmail/signals.py
+++ b/src/pretix/plugins/sendmail/signals.py
@@ -138,6 +138,12 @@ def sendmail_run_rules(sender, **kwargs):
             if m.computed_datetime != previous:
                 m.save(update_fields=['last_computed', 'computed_datetime'])
 
+        mails.filter(
+            state=ScheduledMail.STATE_SCHEDULED,
+            computed_datetime__lte=timezone.now() - datetime.timedelta(days=2),
+        ).update(
+            state=ScheduledMail.STATE_MISSED
+        )
         for m_id in mails.filter(
             state__in=(ScheduledMail.STATE_SCHEDULED, ScheduledMail.STATE_FAILED),
             computed_datetime__gte=timezone.now() - datetime.timedelta(days=2),