diff --git a/.github/ISSUE_TEMPLATE/webtestplan.md b/.github/ISSUE_TEMPLATE/webtestplan.md
index 3a3c94dc8bf34..4937c61de1c59 100644
--- a/.github/ISSUE_TEMPLATE/webtestplan.md
+++ b/.github/ISSUE_TEMPLATE/webtestplan.md
@@ -132,6 +132,8 @@ For each, test the invite, reset, and login flows
 - [ ] Verify that error message is shown if an invite/reset is expired/invalid
 - [ ] Verify that account is locked after several unsuccessful login attempts
 
+- [ ] Verify that after logging in, user is automatically redirected to the login page when the session expires.
+
 #### Auth Connectors
 
 For help with setting up auth connectors, check out the [Quick GitHub/SAML/OIDC Setup Tips]
diff --git a/web/packages/teleport/src/services/websession/websession.test.ts b/web/packages/teleport/src/services/websession/websession.test.ts
new file mode 100644
index 0000000000000..9a13dadc6d515
--- /dev/null
+++ b/web/packages/teleport/src/services/websession/websession.test.ts
@@ -0,0 +1,35 @@
+/**
+ * Teleport
+ * Copyright (C) 2024  Gravitational, Inc.
+ *
+ * This program is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU Affero General Public License as published by
+ * the Free Software Foundation, either version 3 of the License, or
+ * (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU Affero General Public License for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public License
+ * along with this program.  If not, see <http://www.gnu.org/licenses/>.
+ */
+
+import { waitFor } from '@testing-library/react';
+
+import history from 'teleport/services/history';
+
+import websession from '.';
+import api from '../api';
+
+test('user should be redirected to login even if session delete call fails', async () => {
+  jest.spyOn(console, 'error').mockImplementation();
+  jest.spyOn(api, 'delete').mockRejectedValue(new Error('some error'));
+  const goToLoginSpy = jest.spyOn(history, 'goToLogin').mockImplementation();
+  jest.spyOn(websession, 'clear').mockImplementation();
+
+  websession.logout();
+
+  await waitFor(() => expect(goToLoginSpy).toHaveBeenCalled());
+});
diff --git a/web/packages/teleport/src/services/websession/websession.ts b/web/packages/teleport/src/services/websession/websession.ts
index bea98b37ed9f2..c4b3bb0fb975b 100644
--- a/web/packages/teleport/src/services/websession/websession.ts
+++ b/web/packages/teleport/src/services/websession/websession.ts
@@ -36,14 +36,28 @@ let sesstionCheckerTimerId = null;
 
 const session = {
   logout(rememberLocation = false) {
-    api.delete(cfg.api.webSessionPath).then(response => {
-      this.clear();
-      if (response.samlSloUrl) {
-        window.open(response.samlSloUrl, '_self');
-      } else {
-        history.goToLogin({ rememberLocation });
-      }
-    });
+    let samlSloUrl = '';
+
+    api
+      .delete(cfg.api.webSessionPath)
+      .then(response => {
+        samlSloUrl = response?.samlSloUrl;
+      })
+      .catch(err => {
+        // This request can fail if the session is already expired, which isn't an issue, but we should still catch the error.
+        logger.error(
+          'Failed to delete session. This can happen if the session has already expired.',
+          err
+        );
+      })
+      .finally(() => {
+        this.clear();
+        if (samlSloUrl) {
+          window.open(samlSloUrl, '_self');
+        } else {
+          history.goToLogin({ rememberLocation });
+        }
+      });
   },
 
   logoutWithoutSlo({