diff --git a/backend/internal/service/widget_service_test.go b/backend/internal/service/widget_service_test.go
index e80700b6..1591beff 100644
--- a/backend/internal/service/widget_service_test.go
+++ b/backend/internal/service/widget_service_test.go
@@ -202,7 +202,7 @@ func TestWidgetService_RealtimeFailureDoesNotBlockCaptain(t *testing.T) {
 	require.Equal(t, model.BackgroundJobStatusRetrying, realtimeJob.Status)
 }
 
-func TestWidgetService_RealtimeJobFailureRollsBackMessage(t *testing.T) {
+func TestWidgetService_SecondRealtimeJobFailureRollsBackMessage(t *testing.T) {
 	db, svc := setupWidgetServiceTest(t)
 	seedWidgetInbox(t, db)
 	pool := worker.NewWorkerPool(db, nil)
@@ -217,9 +217,11 @@ func TestWidgetService_RealtimeJobFailureRollsBackMessage(t *testing.T) {
 
 	initResp, err := svc.Init(context.Background(), WidgetInitRequest{WebsiteToken: "test_ws_token_123"})
 	require.NoError(t, err)
-	failBackgroundJobCreate(t, db)
+	require.NoError(t, db.Exec(`CREATE TRIGGER fail_token_realtime_job BEFORE INSERT ON background_jobs
+		WHEN CAST(NEW.payload AS TEXT) LIKE '%"target":"pubsub_token"%'
+		BEGIN SELECT RAISE(FAIL, 'forced second realtime job insert failure'); END`).Error)
 	_, err = svc.SendMessage(context.Background(), WidgetSendMessageRequest{WidgetToken: initResp.WidgetToken, Content: "must roll back"})
-	require.ErrorContains(t, err, "forced background job insert failure")
+	require.ErrorContains(t, err, "forced second realtime job insert failure")
 
 	var messages, jobs int64
 	require.NoError(t, db.Model(&model.Message{}).Where("content = ?", "must roll back").Count(&messages).Error)
diff --git a/backend/internal/ws/event_publisher_test.go b/backend/internal/ws/event_publisher_test.go
index 02db3066..7923149f 100644
--- a/backend/internal/ws/event_publisher_test.go
+++ b/backend/internal/ws/event_publisher_test.go
@@ -758,6 +758,32 @@ func TestEventPublisher_WidgetEvent_PubsubTokenRoomDelivery(t *testing.T) {
 	assert.Equal(t, uint(1), roomMsg.AccountID)
 }
 
+func TestEventPublisher_DurableEnqueueKeepsEarlierTargetWhenSecondInsertFails(t *testing.T) {
+	db, err := gorm.Open(sqlite.Open("file:"+t.Name()+"?mode=memory&cache=shared"), &gorm.Config{})
+	require.NoError(t, err)
+	require.NoError(t, db.AutoMigrate(&model.BackgroundJob{}))
+
+	publisher := NewEventPublisherLocal(nil, nil)
+	publisher.SetWorkerPool(worker.NewWorkerPool(db))
+	require.NoError(t, publisher.PublishEvent(1, EventConversationUpdated, map[string]any{"id": 7}))
+
+	var jobs []model.BackgroundJob
+	require.NoError(t, db.Where("job_type = ?", taskTypeRealtimeEventPublish).Find(&jobs).Error)
+	require.Len(t, jobs, 1, "PublishEvent must enqueue its account target")
+	require.NoError(t, db.Exec("DELETE FROM background_jobs").Error)
+	require.NoError(t, db.Exec(`CREATE TRIGGER fail_token_realtime_job BEFORE INSERT ON background_jobs
+		WHEN CAST(NEW.payload AS TEXT) LIKE '%"target":"pubsub_token"%'
+		BEGIN SELECT RAISE(FAIL, 'forced second realtime job insert failure'); END`).Error)
+
+	err = publisher.PublishWidgetEvent(1, "visitor", EventConversationUpdated, map[string]any{"id": 8})
+	require.ErrorContains(t, err, "forced second realtime job insert failure")
+	require.NoError(t, db.Where("job_type = ?", taskTypeRealtimeEventPublish).Find(&jobs).Error)
+	require.Len(t, jobs, 1, "the successful account target must remain durable")
+	var persisted realtimeEventPublishJob
+	require.NoError(t, json.Unmarshal(jobs[0].Payload, &persisted))
+	require.Equal(t, realtimeTargetAccount, persisted.Target)
+}
+
 func TestEventPublisher_DurableWidgetPublishRetriesPartialFailure(t *testing.T) {
 	db, err := gorm.Open(sqlite.Open("file:"+t.Name()+"?mode=memory&cache=shared"), &gorm.Config{})
 	require.NoError(t, err)