fix(issues): Fix auto_ongoing_issues task timeouts (#104036)

Fixes:
SENTRY-4A6K

Author: yuvmen

src/sentry/tasks/auto_ongoing_issues.py

@@ -2,11 +2,11 @@
 from datetime import datetime, timedelta, timezone
 
 import sentry_sdk
-from django.db.models import Max
+from django.db.models import Max, OuterRef, Subquery
 
 from sentry.issues.ongoing import TRANSITION_AFTER_DAYS, bulk_transition_group_to_ongoing
 from sentry.models.group import Group, GroupStatus
-from sentry.models.grouphistory import GroupHistoryStatus
+from sentry.models.grouphistory import GroupHistory, GroupHistoryStatus
 from sentry.silo.base import SiloMode
 from sentry.tasks.base import instrumented_task
 from sentry.taskworker.namespaces import issues_tasks
@@ -163,14 +163,28 @@ def get_total_count(results):
         nonlocal total_count
         total_count += len(results)
 
+    date_threshold = datetime.fromtimestamp(date_added_lte, timezone.utc)
+
+    # Use a subquery to get the most recent REGRESSED history date for each group.
+    # This ensures we only transition groups whose MOST RECENT regressed history
+    # is older than the threshold, not just any regressed history.
+    latest_regressed_subquery = (
+        GroupHistory.objects.filter(group_id=OuterRef("id"), status=GroupHistoryStatus.REGRESSED)
+        .values("group_id")
+        .annotate(max_date=Max("date_added"))
+        .values("max_date")[:1]
+    )
+
     base_queryset = (
         Group.objects.filter(
             status=GroupStatus.UNRESOLVED,
             substatus=GroupSubStatus.REGRESSED,
-            grouphistory__status=GroupHistoryStatus.REGRESSED,
         )
-        .annotate(recent_regressed_history=Max("grouphistory__date_added"))
-        .filter(recent_regressed_history__lte=datetime.fromtimestamp(date_added_lte, timezone.utc))
+        .annotate(recent_regressed_history=Subquery(latest_regressed_subquery))
+        .filter(
+            recent_regressed_history__lte=date_threshold,
+            recent_regressed_history__isnull=False,
+        )
     )
 
     with sentry_sdk.start_span(name="iterate_chunked_group_ids"):
@@ -244,14 +258,30 @@ def get_total_count(results):
         nonlocal total_count
         total_count += len(results)
 
+    from django.db.models import Max, OuterRef, Subquery
+
+    date_threshold = datetime.fromtimestamp(date_added_lte, timezone.utc)
+
+    # Use a subquery to get the most recent ESCALATING history date for each group.
+    # This ensures we only transition groups whose MOST RECENT escalating history
+    # is older than the threshold, not just any escalating history.
+    latest_escalating_subquery = (
+        GroupHistory.objects.filter(group_id=OuterRef("id"), status=GroupHistoryStatus.ESCALATING)
+        .values("group_id")
+        .annotate(max_date=Max("date_added"))
+        .values("max_date")[:1]
+    )
+
     base_queryset = (
         Group.objects.filter(
             status=GroupStatus.UNRESOLVED,
             substatus=GroupSubStatus.ESCALATING,
-            grouphistory__status=GroupHistoryStatus.ESCALATING,
         )
-        .annotate(recent_escalating_history=Max("grouphistory__date_added"))
-        .filter(recent_escalating_history__lte=datetime.fromtimestamp(date_added_lte, timezone.utc))
+        .annotate(recent_escalating_history=Subquery(latest_escalating_subquery))
+        .filter(
+            recent_escalating_history__lte=date_threshold,
+            recent_escalating_history__isnull=False,
+        )
     )
 
     with sentry_sdk.start_span(name="iterate_chunked_group_ids"):

tests/sentry/tasks/test_auto_ongoing_issues.py

@@ -345,6 +345,73 @@ def test_not_all_groups_get_updated(self, mock_metrics_incr) -> None:
             tags={"count": 0},
         )
 
+    @freeze_time("2023-07-12 18:40:00Z")
+    def test_only_checks_most_recent_regressed_history(self) -> None:
+        """
+        Test that only the MOST RECENT regressed history is checked against the threshold,
+        not just any regressed history.
+
+        Scenario:
+        - Group regressed 14 days ago (older than 7-day threshold)
+        - Group resolved 10 days ago
+        - Group regressed again 2 days ago (newer than 7-day threshold)
+
+        Expected: Group should NOT be transitioned because most recent regression is only 2 days old
+        """
+        now = datetime.now(tz=timezone.utc)
+        project = self.create_project()
+        group = self.create_group(
+            project=project,
+            status=GroupStatus.UNRESOLVED,
+            substatus=GroupSubStatus.REGRESSED,
+            first_seen=now - timedelta(days=14),
+        )
+
+        # Create OLD regressed history (14 days ago) - this is OLDER than threshold
+        old_regressed_history = record_group_history(
+            group, GroupHistoryStatus.REGRESSED, actor=None, release=None
+        )
+        old_regressed_history.date_added = now - timedelta(days=14)
+        old_regressed_history.save(update_fields=["date_added"])
+
+        # Create resolved history in between (10 days ago)
+        resolved_history = record_group_history(
+            group, GroupHistoryStatus.RESOLVED, actor=None, release=None
+        )
+        resolved_history.date_added = now - timedelta(days=10)
+        resolved_history.save(update_fields=["date_added"])
+
+        # Create NEW regressed history (2 days ago) - this is NEWER than threshold
+        # This is the MOST RECENT regressed history
+        new_regressed_history = record_group_history(
+            group, GroupHistoryStatus.REGRESSED, actor=None, release=None
+        )
+        new_regressed_history.date_added = now - timedelta(days=2)
+        new_regressed_history.save(update_fields=["date_added"])
+
+        # Also create a recent group inbox entry
+        group_inbox = add_group_to_inbox(group, GroupInboxReason.REGRESSION)
+        group_inbox.date_added = now - timedelta(days=2)
+        group_inbox.save(update_fields=["date_added"])
+
+        with self.tasks():
+            schedule_auto_transition_to_ongoing()
+
+        # Group should NOT be transitioned because most recent regression is only 2 days old
+        group.refresh_from_db()
+        assert group.status == GroupStatus.UNRESOLVED
+        assert group.substatus == GroupSubStatus.REGRESSED  # Should still be REGRESSED
+
+        # Should NOT have created an auto-ongoing activity
+        assert not Activity.objects.filter(
+            group=group, type=ActivityType.AUTO_SET_ONGOING.value
+        ).exists()
+
+        # Should NOT have created an ONGOING history entry
+        assert not GroupHistory.objects.filter(
+            group=group, status=GroupHistoryStatus.ONGOING
+        ).exists()
+
 
 class ScheduleAutoEscalatingOngoingIssuesTest(TestCase):
     @freeze_time("2023-07-12 18:40:00Z")