diff --git a/awx/main/scheduler/__init__.py b/awx/main/scheduler/__init__.py
index 8569fb5cfc..5221f340a6 100644
--- a/awx/main/scheduler/__init__.py
+++ b/awx/main/scheduler/__init__.py
@@ -240,6 +240,9 @@ class TaskManager():
                 dependencies.append(project_task)
                 # Inventory created 2 seconds behind job
 
+            '''
+            Inventory may have already been synced from a provision callback.
+            '''
             inventory_sources_already_updated = task.get_inventory_sources_already_updated()
 
             for inventory_source_task in self.graph.get_inventory_sources(task['inventory_id']):
diff --git a/awx/main/scheduler/dependency_graph.py b/awx/main/scheduler/dependency_graph.py
index 7b66a8fe1b..846a194b27 100644
--- a/awx/main/scheduler/dependency_graph.py
+++ b/awx/main/scheduler/dependency_graph.py
@@ -117,10 +117,6 @@ class DependencyGraph(object):
         if not latest_inventory_update:
             return True
 
-        # TODO: Other finished, failed cases? i.e. error ?
-        if latest_inventory_update['status'] in ['failed', 'canceled']:
-            return True
-
         '''
         This is a bit of fuzzy logic.
         If the latest inventory update has a created time == job_created_time-2
@@ -138,7 +134,11 @@ class DependencyGraph(object):
         timeout_seconds = timedelta(seconds=latest_inventory_update['inventory_source__update_cache_timeout'])
         if (latest_inventory_update['finished'] + timeout_seconds) < now:
             return True
-        
+
+        if latest_inventory_update['inventory_source__update_on_launch'] is True and \
+                latest_inventory_update['status'] in ['failed', 'canceled', 'error']:
+            return True
+
         return False
 
     def mark_system_job(self):
diff --git a/awx/main/scheduler/partial.py b/awx/main/scheduler/partial.py
index d16634f369..18c5c63d46 100644
--- a/awx/main/scheduler/partial.py
+++ b/awx/main/scheduler/partial.py
@@ -151,6 +151,7 @@ class InventoryUpdateLatestDict(InventoryUpdateDict):
     FIELDS = (
         'id', 'status', 'created', 'celery_task_id', 'inventory_source_id', 
         'finished', 'inventory_source__update_cache_timeout', 'launch_type',
+        'inventory_source__update_on_launch',
     )
     model = InventoryUpdate
 
diff --git a/awx/main/tests/unit/scheduler/test_scheduler_inventory_update.py b/awx/main/tests/unit/scheduler/test_scheduler_inventory_update.py
index 5e49eec729..eeace8243d 100644
--- a/awx/main/tests/unit/scheduler/test_scheduler_inventory_update.py
+++ b/awx/main/tests/unit/scheduler/test_scheduler_inventory_update.py
@@ -26,6 +26,22 @@ def successful_inventory_update_latest_cache_expired(inventory_update_latest_fac
     return iu
 
 
+@pytest.fixture
+def failed_inventory_update_latest_cache_zero(failed_inventory_update_latest):
+    iu = failed_inventory_update_latest
+    iu['inventory_source__update_cache_timeout'] = 0
+    iu['inventory_source__update_on_launch'] = True
+    iu['finished'] = iu['created'] + timedelta(seconds=2)
+    iu['status'] = 'failed'
+    return iu
+
+
+@pytest.fixture
+def failed_inventory_update_latest_cache_non_zero(failed_inventory_update_latest_cache_zero):
+    failed_inventory_update_latest_cache_zero['inventory_source__update_cache_timeout'] = 10000000
+    return failed_inventory_update_latest_cache_zero
+
+
 class TestStartInventoryUpdate():
     def test_pending(self, scheduler_factory, pending_inventory_update):
         scheduler = scheduler_factory(tasks=[pending_inventory_update])
@@ -79,9 +95,18 @@ class TestCreateDependentInventoryUpdate():
 
         scheduler.start_task.assert_called_with(waiting_inventory_update, [pending_job])
 
-    def test_last_update_failed(self, scheduler_factory, pending_job, failed_inventory_update, failed_inventory_update_latest, waiting_inventory_update, inventory_id_sources):
+    def test_last_update_timeout_zero_failed(self, scheduler_factory, pending_job, failed_inventory_update, failed_inventory_update_latest_cache_zero, waiting_inventory_update, inventory_id_sources):
         scheduler = scheduler_factory(tasks=[failed_inventory_update, pending_job], 
-                                      latest_inventory_updates=[failed_inventory_update_latest], 
+                                      latest_inventory_updates=[failed_inventory_update_latest_cache_zero], 
+                                      create_inventory_update=waiting_inventory_update,
+                                      inventory_sources=inventory_id_sources)
+        scheduler._schedule()
+
+        scheduler.start_task.assert_called_with(waiting_inventory_update, [pending_job])
+
+    def test_last_update_timeout_non_zero_failed(self, scheduler_factory, pending_job, failed_inventory_update, failed_inventory_update_latest_cache_non_zero, waiting_inventory_update, inventory_id_sources):
+        scheduler = scheduler_factory(tasks=[failed_inventory_update, pending_job], 
+                                      latest_inventory_updates=[failed_inventory_update_latest_cache_non_zero], 
                                       create_inventory_update=waiting_inventory_update,
                                       inventory_sources=inventory_id_sources)
         scheduler._schedule()