diff --git a/python/ray/tune/tests/test_cluster_searcher.py b/python/ray/tune/tests/test_cluster_searcher.py
index 0ee908d00..ab1b9ef8e 100644
--- a/python/ray/tune/tests/test_cluster_searcher.py
+++ b/python/ray/tune/tests/test_cluster_searcher.py
@@ -76,7 +76,7 @@ def test_cluster_interrupt_searcher(start_connected_cluster, tmpdir, searcher):
     # The trainable returns every 0.5 seconds, so this should not miss
     # the checkpoint.
     trials = []
-    for i in range(50):
+    for i in range(100):
         if TrialRunner.checkpoint_exists(local_checkpoint_dir):
             # Inspect the internal trialrunner
             runner = TrialRunner(
@@ -105,7 +105,7 @@ def test_cluster_interrupt_searcher(start_connected_cluster, tmpdir, searcher):
 
     register_trainable("trainable", MyTrainableClass)
     reached = False
-    for i in range(50):
+    for i in range(100):
         if TrialRunner.checkpoint_exists(local_checkpoint_dir):
             # Inspect the internal trialrunner
             runner = TrialRunner(
diff --git a/python/ray/tune/tests/test_progress_reporter.py b/python/ray/tune/tests/test_progress_reporter.py
index 53746d34b..5624faf46 100644
--- a/python/ray/tune/tests/test_progress_reporter.py
+++ b/python/ray/tune/tests/test_progress_reporter.py
@@ -233,14 +233,23 @@ EXPECTED_SORT_RESULT_DESC = """Number of trials: 5 (1 PENDING, 1 RUNNING, 3 TERM
 VERBOSE_EXP_OUT_1 = "Number of trials: 3/3 (2 PENDING, 1 RUNNING)"
 VERBOSE_EXP_OUT_2 = "Number of trials: 3/3 (3 TERMINATED)"
 
-VERBOSE_TRIAL_NORM = (
-    "Trial train_xxxxx_00000 reported acc=5 with "
-    + """parameters={'do': 'complete'}. This trial completed.
+VERBOSE_TRIAL_NORM_1 = (
+    "Trial train_xxxxx_00000 reported acc=5 "
+    "with parameters={'do': 'complete'}. This trial completed.\n"
+)
+
+VERBOSE_TRIAL_NORM_2 = """
 Trial train_xxxxx_00001 reported _metric=6 with parameters={'do': 'once'}.
 Trial train_xxxxx_00001 completed. Last result: _metric=6
+"""
+
+VERBOSE_TRIAL_NORM_3 = """
 Trial train_xxxxx_00002 reported acc=7 with parameters={'do': 'twice'}.
-Trial train_xxxxx_00002 reported acc=8 with parameters={'do': 'twice'}. """
-    + "This trial completed."
+"""
+
+VERBOSE_TRIAL_NORM_4 = (
+    "Trial train_xxxxx_00002 reported acc=8 "
+    "with parameters={'do': 'twice'}. This trial completed.\n"
 )
 
 VERBOSE_TRIAL_DETAIL = """+-------------------+----------+-------------------+----------+
@@ -602,7 +611,10 @@ class ProgressReporterTest(unittest.TestCase):
             try:
                 self.assertNotIn(VERBOSE_EXP_OUT_1, output)
                 self.assertNotIn(VERBOSE_EXP_OUT_2, output)
-                self.assertNotIn(VERBOSE_TRIAL_NORM, output)
+                self.assertNotIn(VERBOSE_TRIAL_NORM_1, output)
+                self.assertNotIn(VERBOSE_TRIAL_NORM_2, output)
+                self.assertNotIn(VERBOSE_TRIAL_NORM_3, output)
+                self.assertNotIn(VERBOSE_TRIAL_NORM_4, output)
                 self.assertNotIn(VERBOSE_TRIAL_DETAIL, output)
             except Exception:
                 print("*** BEGIN OUTPUT ***")
@@ -615,7 +627,10 @@ class ProgressReporterTest(unittest.TestCase):
             try:
                 self.assertIn(VERBOSE_EXP_OUT_1, output)
                 self.assertIn(VERBOSE_EXP_OUT_2, output)
-                self.assertNotIn(VERBOSE_TRIAL_NORM, output)
+                self.assertNotIn(VERBOSE_TRIAL_NORM_1, output)
+                self.assertNotIn(VERBOSE_TRIAL_NORM_2, output)
+                self.assertNotIn(VERBOSE_TRIAL_NORM_3, output)
+                self.assertNotIn(VERBOSE_TRIAL_NORM_4, output)
                 self.assertNotIn(VERBOSE_TRIAL_DETAIL, output)
             except Exception:
                 print("*** BEGIN OUTPUT ***")
@@ -628,7 +643,10 @@ class ProgressReporterTest(unittest.TestCase):
             try:
                 self.assertIn(VERBOSE_EXP_OUT_1, output)
                 self.assertIn(VERBOSE_EXP_OUT_2, output)
-                self.assertIn(VERBOSE_TRIAL_NORM, output)
+                self.assertIn(VERBOSE_TRIAL_NORM_1, output)
+                self.assertIn(VERBOSE_TRIAL_NORM_2, output)
+                self.assertIn(VERBOSE_TRIAL_NORM_3, output)
+                self.assertIn(VERBOSE_TRIAL_NORM_4, output)
                 self.assertNotIn(VERBOSE_TRIAL_DETAIL, output)
             except Exception:
                 print("*** BEGIN OUTPUT ***")
@@ -641,7 +659,10 @@ class ProgressReporterTest(unittest.TestCase):
             try:
                 self.assertIn(VERBOSE_EXP_OUT_1, output)
                 self.assertIn(VERBOSE_EXP_OUT_2, output)
-                self.assertNotIn(VERBOSE_TRIAL_NORM, output)
+                self.assertNotIn(VERBOSE_TRIAL_NORM_1, output)
+                self.assertNotIn(VERBOSE_TRIAL_NORM_2, output)
+                self.assertNotIn(VERBOSE_TRIAL_NORM_3, output)
+                self.assertNotIn(VERBOSE_TRIAL_NORM_4, output)
                 self.assertIn(VERBOSE_TRIAL_DETAIL, output)
             except Exception:
                 print("*** BEGIN OUTPUT ***")
diff --git a/python/ray/tune/tests/test_ray_trial_executor.py b/python/ray/tune/tests/test_ray_trial_executor.py
index dfdd43db5..f9e78b125 100644
--- a/python/ray/tune/tests/test_ray_trial_executor.py
+++ b/python/ray/tune/tests/test_ray_trial_executor.py
@@ -341,7 +341,10 @@ class RayTrialExecutorTest(unittest.TestCase):
         os.environ["TUNE_FORCE_TRIAL_CLEANUP_S"] = "0"
         self._simulate_starting_trial(trial)
         self.assertEqual(Trial.RUNNING, trial.status)
-        time.sleep(1)
+        # This should be enough time for `trial._default_result_or_future`
+        # to return. Otherwise, PID won't show up in `trial.last_result`,
+        # which is asserted down below.
+        time.sleep(2)
         print("Stop trial")
         self.trial_executor.stop_trial(trial)
         print("Start trial cleanup")