diff --git a/python/ray/autoscaler/_private/command_runner.py b/python/ray/autoscaler/_private/command_runner.py
index 3dd0b3d38..f328d4fd6 100644
--- a/python/ray/autoscaler/_private/command_runner.py
+++ b/python/ray/autoscaler/_private/command_runner.py
@@ -598,7 +598,8 @@ class DockerCommandRunner(CommandRunnerInterface):
             shutdown_after_run=False,
     ):
         if run_env == "auto":
-            run_env = "host" if cmd.find("docker") == 0 else "docker"
+            run_env = "host" if (not bool(cmd)
+                                 or cmd.find("docker") == 0) else "docker"
 
         if environment_variables:
             cmd = _with_environment_variables(cmd, environment_variables)
diff --git a/python/ray/tests/test_cli.py b/python/ray/tests/test_cli.py
index 1f940674a..57bf61419 100644
--- a/python/ray/tests/test_cli.py
+++ b/python/ray/tests/test_cli.py
@@ -319,6 +319,30 @@ def test_ray_attach(configure_lang, configure_aws, _unlink_test_ssh_key):
         _check_output_via_pattern("test_ray_attach.txt", result)
 
 
+@pytest.mark.skipif(
+    sys.platform == "darwin" and "travis" in os.environ.get("USER", ""),
+    reason=("Mac builds don't provide proper locale support"))
+@mock_ec2
+@mock_iam
+def test_ray_dashboard(configure_lang, configure_aws, _unlink_test_ssh_key):
+    def commands_mock(command, stdin):
+        # TODO(maximsmol): this is a hack since stdout=sys.stdout
+        #                  doesn't work with the mock for some reason
+        print("ubuntu@ip-.+:~$ exit")
+        return PopenBehaviour(stdout="ubuntu@ip-.+:~$ exit")
+
+    with _setup_popen_mock(commands_mock):
+        runner = CliRunner()
+        result = runner.invoke(scripts.up, [
+            DEFAULT_TEST_CONFIG_PATH, "--no-config-cache", "-y",
+            "--log-style=pretty", "--log-color", "False"
+        ])
+        _die_on_error(result)
+
+        result = runner.invoke(scripts.dashboard, [DEFAULT_TEST_CONFIG_PATH])
+        _check_output_via_pattern("test_ray_dashboard.txt", result)
+
+
 @pytest.mark.skipif(
     sys.platform == "darwin" and "travis" in os.environ.get("USER", ""),
     reason=("Mac builds don't provide proper locale support"))
diff --git a/python/ray/tests/test_cli_patterns/test_ray_dashboard.txt b/python/ray/tests/test_cli_patterns/test_ray_dashboard.txt
new file mode 100644
index 000000000..3f7aaf070
--- /dev/null
+++ b/python/ray/tests/test_cli_patterns/test_ray_dashboard.txt
@@ -0,0 +1,7 @@
+Attempting to establish dashboard locally at localhost:8265 connected to remote port 8265
+Loaded cached provider configuration
+If you experience issues with the cloud provider, try re-running the command with --no-config-cache.
+Fetched IP: .+
+Forwarding ports
+ubuntu@ip-.+:~\$ exit
+Successfully established connection.