diff --git a/netbox/netbox/middleware.py b/netbox/netbox/middleware.py
index 4a36c2d98..a9ee93fc6 100644
--- a/netbox/netbox/middleware.py
+++ b/netbox/netbox/middleware.py
@@ -10,7 +10,9 @@ from django.db import ProgrammingError, connection
 from django.db.utils import InternalError
 from django.http import Http404, HttpResponseRedirect
 from django.middleware.common import CommonMiddleware as DjangoCommonMiddleware
+from django.utils.translation import gettext_lazy as _
 from django_prometheus import middleware
+from social_django.middleware import SocialAuthExceptionMiddleware as SocialAuthExceptionMiddleware_
 
 from netbox.config import clear_config, get_config
 from netbox.metrics import Metrics
@@ -26,6 +28,7 @@ __all__ = (
     'PrometheusAfterMiddleware',
     'PrometheusBeforeMiddleware',
     'RemoteUserMiddleware',
+    'SocialAuthExceptionMiddleware',
 )
 
 
@@ -286,3 +289,13 @@ class MaintenanceModeMiddleware:
             messages.error(request, error_message)
             return HttpResponseRedirect(request.path_info)
         return None
+
+
+class SocialAuthExceptionMiddleware(SocialAuthExceptionMiddleware_):
+    """
+    Subclass of python-social-auth's exception middleware which surfaces a generic, user-friendly
+    message rather than exposing the raw social_core exception text to (typically unauthenticated)
+    users when an SSO/SAML login fails.
+    """
+    def get_message(self, request, exception):
+        return _("Single sign-on failed. Please try again or contact your administrator.")
diff --git a/netbox/netbox/settings.py b/netbox/netbox/settings.py
index e449d0688..cd5fb2e4e 100644
--- a/netbox/netbox/settings.py
+++ b/netbox/netbox/settings.py
@@ -516,6 +516,7 @@ MIDDLEWARE = [
     'netbox.middleware.RemoteUserMiddleware',
     'netbox.middleware.CoreMiddleware',
     'netbox.middleware.MaintenanceModeMiddleware',
+    'netbox.middleware.SocialAuthExceptionMiddleware',
 ]
 
 if DEBUG:
@@ -725,6 +726,13 @@ SOCIAL_AUTH_PIPELINE = (
     'social_core.pipeline.user.user_details',
 )
 
+# Redirect users back to the login page (surfacing the error via the messages framework) when an
+# SSO/SAML authentication failure occurs, rather than raising an HTTP 500. Full exceptions are still
+# raised when DEBUG is enabled. LOGIN_URL is an absolute path which respects BASE_PATH; the social
+# auth middleware passes this value directly to an HttpResponseRedirect without reversing it.
+SOCIAL_AUTH_LOGIN_ERROR_URL = LOGIN_URL
+SOCIAL_AUTH_RAISE_EXCEPTIONS = DEBUG
+
 # Load all SOCIAL_AUTH_* settings from the user configuration
 for param in dir(configuration):
     if param.startswith('SOCIAL_AUTH_'):
diff --git a/netbox/netbox/tests/test_authentication.py b/netbox/netbox/tests/test_authentication.py
index 55298cb2f..5221fe4b8 100644
--- a/netbox/netbox/tests/test_authentication.py
+++ b/netbox/netbox/tests/test_authentication.py
@@ -1,13 +1,16 @@
 import datetime
 
 from django.conf import settings
-from django.test import Client
+from django.contrib.messages.storage.fallback import FallbackStorage
+from django.test import Client, RequestFactory, SimpleTestCase
 from django.test.utils import override_settings
 from django.urls import reverse
 from rest_framework.test import APIClient
+from social_core.exceptions import AuthFailed
 
 from core.models import ObjectType
 from dcim.models import Rack, Site
+from netbox.middleware import SocialAuthExceptionMiddleware
 from users.constants import TOKEN_PREFIX
 from users.models import Group, ObjectPermission, Token, User
 from utilities.testing import TestCase
@@ -697,3 +700,56 @@ class ObjectPermissionAPIViewTestCase(TestCase):
         url = reverse('dcim-api:rack-detail', kwargs={'pk': self.racks[0].pk})
         response = self.client.delete(url, format='json', **self.header)
         self.assertEqual(response.status_code, 204)
+
+
+class SocialAuthExceptionMiddlewareTestCase(SimpleTestCase):
+    """
+    Verify that SSO/SAML authentication failures are surfaced as a login-page message rather than
+    bubbling up as an HTTP 500 (see #22346).
+    """
+    GENERIC_MESSAGE = "Single sign-on failed. Please try again or contact your administrator."
+
+    class FakeStrategy:
+        # Mirror social_core's DjangoStrategy.setting(), which reads SOCIAL_AUTH_<NAME> from Django
+        # settings. This ensures the test exercises the real configured values (e.g.
+        # SOCIAL_AUTH_LOGIN_ERROR_URL) rather than hardcoded stand-ins.
+        def setting(self, name, default=None, backend=None):
+            return getattr(settings, f'SOCIAL_AUTH_{name}', default)
+
+    class FakeBackend:
+        name = 'saml'
+
+    def setUp(self):
+        self.factory = RequestFactory()
+        self.middleware = SocialAuthExceptionMiddleware(lambda request: None)
+
+    def _make_request(self):
+        request = self.factory.get('/')
+        request.social_strategy = self.FakeStrategy()
+        request.backend = self.FakeBackend()
+        # Attach message storage (normally provided by MessageMiddleware)
+        setattr(request, 'session', {})
+        request._messages = FallbackStorage(request)
+        return request
+
+    def test_generic_message(self):
+        """
+        The raw exception text should never be surfaced to the user.
+        """
+        request = self._make_request()
+        exception = AuthFailed(self.FakeBackend(), 'raw internal SAML detail')
+        self.assertEqual(self.middleware.get_message(request, exception), self.GENERIC_MESSAGE)
+
+    def test_redirect_on_failure(self):
+        """
+        A SocialAuthBaseException should redirect to the login page with the generic message set.
+        """
+        request = self._make_request()
+        exception = AuthFailed(self.FakeBackend(), 'raw internal SAML detail')
+        response = self.middleware.process_exception(request, exception)
+
+        self.assertEqual(response.status_code, 302)
+        self.assertEqual(response.url, settings.SOCIAL_AUTH_LOGIN_ERROR_URL)
+        self.assertEqual(response.url, settings.LOGIN_URL)
+        messages = [str(m) for m in request._messages]
+        self.assertEqual(messages, [self.GENERIC_MESSAGE])