diff --git a/dojo/tasks.py b/dojo/tasks.py
index 1bbe104783b..f09f8c783f6 100644
--- a/dojo/tasks.py
+++ b/dojo/tasks.py
@@ -138,8 +138,11 @@ def _async_dupe_delete_impl():
         originals_with_too_many_duplicates = Finding.objects.filter(id__in=originals_with_too_many_duplicates_ids).order_by("id")
 
         # prefetch to make it faster
+        # Oldest-first: delete from the front of the list until dupe_count <= 0, keeping the last max_dupes.
+        # order_by("date") alone leaves ties undefined when many duplicates share the same date (e.g. tool date);
+        # add id so we always drop lower-id (older) rows first and retain higher-id (newer) imports.
         originals_with_too_many_duplicates = originals_with_too_many_duplicates.prefetch_related(Prefetch("original_finding",
-            queryset=Finding.objects.filter(duplicate=True).order_by("date")))
+            queryset=Finding.objects.filter(duplicate=True).order_by("date", "id")))
 
         total_deleted_count = 0
         affected_products = set()
diff --git a/unittests/test_duplication_loops.py b/unittests/test_duplication_loops.py
index a2afbeb37f9..a3a70cf5c2b 100644
--- a/unittests/test_duplication_loops.py
+++ b/unittests/test_duplication_loops.py
@@ -407,6 +407,43 @@ def test_delete_duplicate_order(self):
         self.finding_a.refresh_from_db()
         self.assertEqual(self.finding_a.duplicate_finding_set().count(), 1)
 
+    def test_delete_duplicate_order_same_date_tiebreak_by_id(self):
+        """When duplicate findings share the same date, excess deletes use id as tie-break (oldest id first)."""
+        system_settings = System_Settings.objects.get()
+        system_settings.delete_duplicates = True
+        system_settings.max_dupes = 1
+        system_settings.save()
+
+        same_date = "2024-06-01"
+        self.finding_b.date = same_date
+        self.finding_c.date = same_date
+        self.finding_b.save()
+        self.finding_c.save()
+
+        set_duplicate(self.finding_b, self.finding_a)
+        set_duplicate(self.finding_c, self.finding_a)
+
+        self.finding_b.refresh_from_db()
+        self.finding_c.refresh_from_db()
+        self.assertLess(
+            self.finding_b.id,
+            self.finding_c.id,
+            "Fixture setup should give finding_b a lower id than finding_c for this tie-break.",
+        )
+
+        _async_dupe_delete_impl()
+
+        self.assertFalse(
+            Finding.objects.filter(id=self.finding_b.id).exists(),
+            "The duplicate with lower id should be deleted when dates are identical.",
+        )
+        self.assertTrue(
+            Finding.objects.filter(id=self.finding_c.id).exists(),
+            "The duplicate with higher id should remain when dates are identical.",
+        )
+        self.finding_a.refresh_from_db()
+        self.assertEqual(self.finding_a.duplicate_finding_set().count(), 1)
+
     def test_delete_all_engagements(self):
         # make sure there is no exception when deleting all engagements
         for engagement in Engagement.objects.all().order_by("id"):