diff --git a/tripleoclient/tests/v1/overcloud_deploy/test_overcloud_deploy.py b/tripleoclient/tests/v1/overcloud_deploy/test_overcloud_deploy.py
index e5cd63859..d866dfe0d 100644
--- a/tripleoclient/tests/v1/overcloud_deploy/test_overcloud_deploy.py
+++ b/tripleoclient/tests/v1/overcloud_deploy/test_overcloud_deploy.py
@@ -886,6 +886,20 @@ class TestDeployOvercloud(fakes.TestDeployOvercloud):
                           '/fake/path', mock.ANY, mock.ANY, mock.ANY,
                           mock.ANY, mock.ANY)
 
+    @mock.patch('tripleoclient.v1.overcloud_deploy.DeployOvercloud.'
+                '_heat_deploy', autospec=True)
+    def test_try_overcloud_deploy_show_missing_file(
+            self, mock_heat_deploy_func):
+        mock_heat_deploy_func.side_effect = [
+            six.moves.urllib.error.URLError('/fake/path not found')
+            for stack_file in constants.OVERCLOUD_YAML_NAMES]
+        try:
+            self.cmd._try_overcloud_deploy_with_compat_yaml(
+                '/fake/path', mock.ANY, mock.ANY, mock.ANY,
+                mock.ANY, mock.ANY)
+        except ValueError as value_error:
+            self.assertIn('/fake/path', str(value_error))
+
     @mock.patch('tripleoclient.utils.create_tempest_deployer_input',
                 autospec=True)
     @mock.patch('tripleoclient.utils.create_overcloudrc', autospec=True)
diff --git a/tripleoclient/v1/overcloud_deploy.py b/tripleoclient/v1/overcloud_deploy.py
index 5dcd80e0b..6ed44ccca 100644
--- a/tripleoclient/v1/overcloud_deploy.py
+++ b/tripleoclient/v1/overcloud_deploy.py
@@ -402,18 +402,17 @@ class DeployOvercloud(command.Command):
     def _try_overcloud_deploy_with_compat_yaml(self, tht_root, stack,
                                                stack_name, parameters,
                                                environments, timeout):
+        messages = ['The following errors occurred:']
         for overcloud_yaml_name in constants.OVERCLOUD_YAML_NAMES:
             overcloud_yaml = os.path.join(tht_root, overcloud_yaml_name)
             try:
                 self._heat_deploy(stack, stack_name, overcloud_yaml,
                                   parameters, environments, timeout)
-            except six.moves.urllib.error.URLError:
-                pass
+            except six.moves.urllib.error.URLError as e:
+                messages.append(str(e.reason))
             else:
                 return
-        message = "The files {0} not found in the {1} directory".format(
-            constants.OVERCLOUD_YAML_NAMES, tht_root)
-        raise ValueError(message)
+        raise ValueError('\n'.join(messages))
 
     def _is_tls_enabled(self, overcloud_endpoint):
         return overcloud_endpoint.startswith('https')