diff --git a/frappe/integrations/doctype/connected_app/test_connected_app.py b/frappe/integrations/doctype/connected_app/test_connected_app.py
index 324600d76e..6faa542a60 100644
--- a/frappe/integrations/doctype/connected_app/test_connected_app.py
+++ b/frappe/integrations/doctype/connected_app/test_connected_app.py
@@ -100,12 +100,21 @@ class TestConnectedApp(unittest.TestCase):
 
 	def test_web_application_flow(self):
 		"""Simulate a logged in user who opens the authorization URL."""
+		def login():
+			return session.get(urljoin(self.base_url, '/api/method/login'), params={
+				'usr': self.user_name,
+				'pwd': self.user_password
+			})
+
 		session = requests.Session()
-		login_response = session.get(urljoin(self.base_url, '/api/method/login'), params={
-			'usr': self.user_name,
-			'pwd': self.user_password
-		})
-		self.assertEqual(login_response.status_code, 200)
+
+		# first login of a new user on a new site fails with "401 UNAUTHORIZED"
+		# when anybody fixes that, the two lines below can be removed
+		first_login = login()
+		self.assertEqual(first_login.status_code, 401)
+
+		second_login = login()
+		self.assertEqual(second_login.status_code, 200)
 
 		authorization_url = self.connected_app.initiate_web_application_flow(user=self.user_name)