diff --git a/scripts/triggered_mails.py b/scripts/triggered_mails.py
index 81da30645d3..13461c628a9 100644
--- a/scripts/triggered_mails.py
+++ b/scripts/triggered_mails.py
@@ -2,7 +2,7 @@
 import uuid
 
 from django.db import transaction
-from django.db.models import Q, Exists, OuterRef
+from django.db.models import Q, F
 from django.utils import timezone
 
 from framework.celery_tasks import app as celery_app
@@ -81,7 +81,10 @@ def find_inactive_users_without_enqueued_or_sent_no_login():
     # Exclude users who have already received a no-login email recently
     return base_q.filter(
         Q(no_login_email_last_sent__isnull=True) |
-        Q(no_login_email_last_sent__lt=now - settings.NO_LOGIN_WAIT_TIME)
+        (
+            Q(no_login_email_last_sent__lt=now - settings.NO_LOGIN_WAIT_TIME) &
+            Q(no_login_email_last_sent__lt=F('date_last_login'))
+        )
     )
 
 
diff --git a/tests/test_triggered_mails.py b/tests/test_triggered_mails.py
index 30f6159ed8c..7e0af23e023 100644
--- a/tests/test_triggered_mails.py
+++ b/tests/test_triggered_mails.py
@@ -127,6 +127,27 @@ def test_finder_excludes_users_with_existing_task(self):
         ids = {u.id for u in users}
         assert ids == {u1.id}  # u2 excluded because of existing task
 
+    def test_finder_excludes_users_logged_in_before_no_login_email_last_sent(self):
+        """Inactive users but one already has a no_login_email_last_sent -> excluded."""
+        u1 = UserFactory(fullname='Jalen Hurts')
+        u2 = UserFactory(fullname='Jason Kelece')
+        u1.date_last_login = _inactive_time() - timedelta(weeks=2)
+        u2.date_last_login = _inactive_time() - timedelta(weeks=2)  # old login, but still inactive
+        u2.no_login_email_last_sent = timezone.now() - timedelta(weeks=53)  # old enough to be eligible if not for the login
+        u1.save()
+        u2.save()
+
+        users = list(find_inactive_users_without_enqueued_or_sent_no_login())
+        ids = {u.id for u in users}
+        assert ids == {u1.id}  # u2 excluded because last login was before email was sent
+
+        u2.date_last_login = timezone.now() - timedelta(weeks=53)
+        u2.save()
+
+        users = list(find_inactive_users_without_enqueued_or_sent_no_login())
+        ids = {u.id for u in users}
+        assert ids == {u1.id, u2.id}  # u2 included again because they logged in after the email was sent
+
     @override_switch(features.ENABLE_NO_LOGIN_EMAILS, active=False)
     def test_disable_task(self):
         u1 = UserFactory(fullname='Jalen Hurts')