diff --git a/python/ray/autoscaler/commands.py b/python/ray/autoscaler/commands.py
index be1b5a144..25544c3bd 100644
--- a/python/ray/autoscaler/commands.py
+++ b/python/ray/autoscaler/commands.py
@@ -379,7 +379,7 @@ def exec_cluster(config_file, cmd, docker, screen, tmux, stop, start,
             cmd,
             screen,
             tmux,
-            expect_error=stop,
+            expect_error=True,
             port_forward=port_forward)
 
         if tmux or screen:
diff --git a/python/ray/autoscaler/updater.py b/python/ray/autoscaler/updater.py
index 9ddf9b56f..f34d4d600 100644
--- a/python/ray/autoscaler/updater.py
+++ b/python/ray/autoscaler/updater.py
@@ -291,12 +291,20 @@ class NodeUpdater(object):
                 "-L", "{}:localhost:{}".format(port_forward, port_forward)
             ]
 
-        self.get_caller(expect_error)(
-            ssh + ssh_opt + get_default_ssh_options(
-                self.ssh_private_key, connect_timeout, self.ssh_control_path) +
-            ["{}@{}".format(self.ssh_user, self.ssh_ip), cmd],
-            stdout=redirect or sys.stdout,
-            stderr=redirect or sys.stderr)
+        final_cmd = ssh + ssh_opt + get_default_ssh_options(
+            self.ssh_private_key, connect_timeout, self.ssh_control_path) + [
+                "{}@{}".format(self.ssh_user, self.ssh_ip), cmd
+            ]
+
+        try:
+            self.get_caller(expect_error)(
+                final_cmd,
+                stdout=redirect or sys.stdout,
+                stderr=redirect or sys.stderr)
+        except subprocess.CalledProcessError:
+            logger.error("Command failed: \n\n  {}\n".format(
+                " ".join(final_cmd)))
+            sys.exit(1)
 
 
 class NodeUpdaterThread(NodeUpdater, Thread):