diff --git a/cura/API/Account.py b/cura/API/Account.py
index 8a8b708cfa..30401454b3 100644
--- a/cura/API/Account.py
+++ b/cura/API/Account.py
@@ -76,6 +76,9 @@ class Account(QObject):
                 self._error_message.hide()
             self._error_message = Message(error_message, title = i18n_catalog.i18nc("@info:title", "Login failed"))
             self._error_message.show()
+            self._logged_in = False
+            self.loginStateChanged.emit(False)
+            return
 
         if self._logged_in != logged_in:
             self._logged_in = logged_in
diff --git a/cura/OAuth2/AuthorizationService.py b/cura/OAuth2/AuthorizationService.py
index a76e8cf304..355db1f1a0 100644
--- a/cura/OAuth2/AuthorizationService.py
+++ b/cura/OAuth2/AuthorizationService.py
@@ -9,12 +9,16 @@ import requests.exceptions
 
 
 from UM.Logger import Logger
+from UM.Message import Message
 from UM.Signal import Signal
 
 from cura.OAuth2.LocalAuthorizationServer import LocalAuthorizationServer
 from cura.OAuth2.AuthorizationHelpers import AuthorizationHelpers, TOKEN_TIMESTAMP_FORMAT
 from cura.OAuth2.Models import AuthenticationResponse
 
+from UM.i18n import i18nCatalog
+i18n_catalog = i18nCatalog("cura")
+
 if TYPE_CHECKING:
     from cura.OAuth2.Models import UserProfile, OAuth2Settings
     from UM.Preferences import Preferences
@@ -41,6 +45,14 @@ class AuthorizationService:
         self._preferences = preferences
         self._server = LocalAuthorizationServer(self._auth_helpers, self._onAuthStateChanged, daemon=True)
 
+        self._unable_to_get_data_message = None
+
+        self.onAuthStateChanged.connect(self._authChanged)
+
+    def _authChanged(self, logged_in):
+        if logged_in and self._unable_to_get_data_message is not None:
+            self._unable_to_get_data_message.hide()
+
     def initialize(self, preferences: Optional["Preferences"] = None) -> None:
         if preferences is not None:
             self._preferences = preferences
@@ -162,7 +174,18 @@ class AuthorizationService:
             preferences_data = json.loads(self._preferences.getValue(self._settings.AUTH_DATA_PREFERENCE_KEY))
             if preferences_data:
                 self._auth_data = AuthenticationResponse(**preferences_data)
-                self.onAuthStateChanged.emit(logged_in=True)
+                # Also check if we can actually get the user profile information.
+                user_profile = self.getUserProfile()
+                if user_profile is not None:
+                    self.onAuthStateChanged.emit(logged_in=True)
+                else:
+                    if self._unable_to_get_data_message is not None:
+                        self._unable_to_get_data_message.hide()
+
+                    self._unable_to_get_data_message = Message(i18n_catalog.i18nc("@info", "Unable to reach the Ultimaker account server."), title = i18n_catalog.i18nc("@info:title", "Warning"))
+                    self._unable_to_get_data_message.addAction("retry", i18n_catalog.i18nc("@action:button", "Retry"), "[no_icon]", "[no_description]")
+                    self._unable_to_get_data_message.actionTriggered.connect(self._onMessageActionTriggered)
+                    self._unable_to_get_data_message.show()
         except ValueError:
             Logger.logException("w", "Could not load auth data from preferences")
 
@@ -179,3 +202,7 @@ class AuthorizationService:
         else:
             self._user_profile = None
             self._preferences.resetPreference(self._settings.AUTH_DATA_PREFERENCE_KEY)
+
+    def _onMessageActionTriggered(self, _, action):
+        if action == "retry":
+            self.loadAuthDataFromPreferences()