diff --git a/tom_observations/cadences/retry_failed_observations.py b/tom_observations/cadences/retry_failed_observations.py
index fc15217bb..264ad736b 100644
--- a/tom_observations/cadences/retry_failed_observations.py
+++ b/tom_observations/cadences/retry_failed_observations.py
@@ -23,33 +23,57 @@ class RetryFailedObservationsStrategy(CadenceStrategy):
     form = RetryFailedObservationsForm
 
     def run(self):
-        failed_observations = [obsr for obsr
-                               in self.dynamic_cadence.observation_group.observation_records.all()
-                               if obsr.failed]
+        records = self.dynamic_cadence.observation_group.observation_records.all().order_by('-created')
+        last_obs = records.first()
+
+        if not last_obs:
+            return
+
+        facility_class = get_service_class(last_obs.facility)
+        facility = facility_class()
+        facility.update_observation_status(last_obs.observation_id)
+        last_obs.refresh_from_db()
+
+        if not last_obs.terminal:
+            return
+        elif last_obs.status == 'COMPLETED':
+            self.dynamic_cadence.active = False
+            self.dynamic_cadence.save()
+            return
+
+        if not last_obs.failed:
+            return
+
+        observation_payload = last_obs.parameters.copy()
+
+        start_keyword, end_keyword = facility.get_start_end_keywords()
+        observation_payload = self.advance_window(
+            observation_payload, start_keyword=start_keyword, end_keyword=end_keyword
+        )
+
+        obs_type = observation_payload.get('observation_type')
+        form = facility.get_form(obs_type)(observation_payload)
+
+        if not form.is_valid():
+            return
+
+        observation_ids = facility.submit_observation(form.observation_payload())
         new_observations = []
-        for obs in failed_observations:
-            observation_payload = obs.parameters
-            facility = get_service_class(obs.facility)()
-            start_keyword, end_keyword = facility.get_start_end_keywords()
-            observation_payload = self.advance_window(
-                observation_payload, start_keyword=start_keyword, end_keyword=end_keyword
+
+        for observation_id in observation_ids:
+            record = ObservationRecord.objects.create(
+                target=last_obs.target,
+                facility=facility.name,
+                parameters=observation_payload,
+                observation_id=observation_id
             )
-            obs_type = obs.parameters.get('observation_type', None)
-            form = facility.get_form(obs_type)(data=observation_payload)
-            form.is_valid()
-            observation_ids = facility.submit_observation(form.observation_payload())
-
-            for observation_id in observation_ids:
-                # Create Observation record
-                record = ObservationRecord.objects.create(
-                    target=obs.target,
-                    facility=facility.name,
-                    parameters=observation_payload,
-                    observation_id=observation_id
-                )
-                self.dynamic_cadence.observation_group.observation_records.add(record)
-                self.dynamic_cadence.observation_group.save()
-                new_observations.append(record)
+            self.dynamic_cadence.observation_group.observation_records.add(record)
+            new_observations.append(record)
+
+        self.dynamic_cadence.observation_group.save()
+
+        for obsr in new_observations:
+            facility.update_observation_status(obsr.observation_id)
 
         return new_observations
 
diff --git a/tom_observations/tests/test_cadence.py b/tom_observations/tests/test_cadence.py
index 66cf49511..a106168ae 100644
--- a/tom_observations/tests/test_cadence.py
+++ b/tom_observations/tests/test_cadence.py
@@ -59,7 +59,9 @@ def setUp(self):
             cadence_strategy='Test Strategy', cadence_parameters={'cadence_frequency': 72}, active=True,
             observation_group=self.group)
 
-    def test_retry_when_failed_cadence(self, patch1, patch2, patch3, patch4):
+    @patch('tom_observations.facilities.lco.LCOFacility.get_observation_status', return_value={'state': 'CANCELED',
+           'scheduled_start': None, 'scheduled_end': None})
+    def test_retry_when_failed_cadence(self, patch1, patch2, patch3, patch4, mock_get_obs_status):
         num_records = self.group.observation_records.count()
         observing_record = self.group.observation_records.first()
         observing_record.status = 'CANCELED'