diff --git a/x-pack/test/functional/page_objects/security_page.ts b/x-pack/test/functional/page_objects/security_page.ts
index 2f0da92a2a6be..8ff8b58f44caf 100644
--- a/x-pack/test/functional/page_objects/security_page.ts
+++ b/x-pack/test/functional/page_objects/security_page.ts
@@ -16,7 +16,11 @@ interface LoginOptions {
   expectForbidden?: boolean;
 }
 
-type LoginExpectedResult = 'spaceSelector' | 'error' | 'chrome';
+type LoginExpectedResult =
+  | 'spaceSelector'
+  | 'error'
+  | 'chrome'
+  | (() => unknown | Promise<unknown>);
 
 export class SecurityPageObject extends FtrService {
   private readonly browser = this.ctx.getService('browser');
@@ -77,7 +81,13 @@ export class SecurityPageObject extends FtrService {
   });
 
   public loginSelector = Object.freeze({
-    login: async (providerType: string, providerName: string, options?: Record<string, any>) => {
+    login: async (
+      providerType: string,
+      providerName: string,
+      options?: Omit<Record<string, any>, 'expectedLoginResult'> & {
+        expectedLoginResult?: LoginExpectedResult;
+      }
+    ) => {
       this.log.debug(`Starting login flow for ${providerType}/${providerName}`);
 
       await this.loginSelector.verifyLoginSelectorIsVisible();
@@ -97,7 +107,7 @@ export class SecurityPageObject extends FtrService {
         await this.testSubjects.click('loginSubmit');
       }
 
-      await this.waitForLoginResult('chrome');
+      await this.waitForLoginResult(options?.expectedLoginResult ?? 'chrome');
 
       this.log.debug(`Finished login process currentUrl = ${await this.browser.getCurrentUrl()}`);
     },
@@ -211,6 +221,13 @@ export class SecurityPageObject extends FtrService {
       await this.find.byCssSelector('[data-test-subj="userMenuButton"]', 20000);
       this.log.debug(`Finished login process currentUrl = ${await this.browser.getCurrentUrl()}`);
     }
+
+    if (expectedResult instanceof Function) {
+      await expectedResult();
+      this.log.debug(
+        `Finished login process, await for custom condition. currentUrl = ${await this.browser.getCurrentUrl()}`
+      );
+    }
   }
 
   async initTests() {
diff --git a/x-pack/test/security_functional/fixtures/common/test_endpoints/public/plugin.tsx b/x-pack/test/security_functional/fixtures/common/test_endpoints/public/plugin.tsx
index 2796d64c01a58..b0264998db17d 100644
--- a/x-pack/test/security_functional/fixtures/common/test_endpoints/public/plugin.tsx
+++ b/x-pack/test/security_functional/fixtures/common/test_endpoints/public/plugin.tsx
@@ -11,10 +11,13 @@ import React from 'react';
 
 export class TestEndpointsPlugin implements Plugin {
   public setup(core: CoreSetup) {
+    // Prevent auto-logout on server `401` errors.
+    core.http.anonymousPaths.register('/authentication/app');
     core.application.register({
       id: 'authentication_app',
       title: 'Authentication app',
       appRoute: '/authentication/app',
+      chromeless: true,
       async mount({ element }) {
         ReactDOM.render(
           <div data-test-subj="testEndpointsAuthenticationApp">Authenticated!</div>,
diff --git a/x-pack/test/security_functional/tests/login_selector/basic_functionality.ts b/x-pack/test/security_functional/tests/login_selector/basic_functionality.ts
index 1eba7a4df31d8..b8c0859541eb9 100644
--- a/x-pack/test/security_functional/tests/login_selector/basic_functionality.ts
+++ b/x-pack/test/security_functional/tests/login_selector/basic_functionality.ts
@@ -17,8 +17,7 @@ export default function ({ getService, getPageObjects }: FtrProviderContext) {
   const deployment = getService('deployment');
   const PageObjects = getPageObjects(['security', 'common']);
 
-  // Failing: See https://github.com/elastic/kibana/issues/98562
-  describe.skip('Basic functionality', function () {
+  describe('Basic functionality', function () {
     this.tags('includeFirefox');
 
     const testCredentials = { username: 'admin_user', password: 'change_me' };
@@ -121,7 +120,10 @@ export default function ({ getService, getPageObjects }: FtrProviderContext) {
         .post('/authentication/app/setup')
         .send({ simulateUnauthorized: false })
         .expect(200);
-      await PageObjects.security.loginSelector.login('basic', 'basic1');
+      await PageObjects.security.loginSelector.login('basic', 'basic1', {
+        // By default, login waits till chrome appears, but the test authentication app is a chromeless app.
+        expectedLoginResult: () => testSubjects.waitForEnabled('testEndpointsAuthenticationApp'),
+      });
 
       const currentURL = parse(await browser.getCurrentUrl());
       expect(currentURL.path).to.eql('/authentication/app?one=two');
@@ -129,16 +131,14 @@ export default function ({ getService, getPageObjects }: FtrProviderContext) {
 
     it('can login after `Unauthorized` error during request authentication preserving original URL', async () => {
       // 1. Navigate to Kibana to make sure user is properly authenticated.
-      await PageObjects.common.navigateToUrl('management', 'security/users', {
-        ensureCurrentUrl: false,
-        shouldLoginIfPrompted: false,
-        shouldUseHashForSubUrl: false,
-      });
+      await browser.get(`${deployment.getHostPort()}/authentication/app?one=two`);
       await PageObjects.security.loginSelector.verifyLoginSelectorIsVisible();
-      await PageObjects.security.loginSelector.login('basic', 'basic1', testCredentials);
-      expect(parse(await browser.getCurrentUrl()).pathname).to.eql(
-        '/app/management/security/users'
-      );
+      await PageObjects.security.loginSelector.login('basic', 'basic1', {
+        ...testCredentials,
+        // By default, login waits till chrome appears, but the test authentication app is a chromeless app.
+        expectedLoginResult: () => testSubjects.waitForEnabled('testEndpointsAuthenticationApp'),
+      });
+      expect(parse(await browser.getCurrentUrl()).pathname).to.eql('/authentication/app');
 
       // 2. Now disable user and try to refresh page causing authentication to fail.
       await security.user.disable(testCredentials.username);
@@ -150,10 +150,12 @@ export default function ({ getService, getPageObjects }: FtrProviderContext) {
 
       // 3. Re-enable user and try to login again.
       await security.user.enable(testCredentials.username);
-      await PageObjects.security.loginSelector.login('basic', 'basic1', testCredentials);
-      expect(parse(await browser.getCurrentUrl()).pathname).to.eql(
-        '/app/management/security/users'
-      );
+      await PageObjects.security.loginSelector.login('basic', 'basic1', {
+        ...testCredentials,
+        // By default, login waits till chrome appears, but the test authentication app is a chromeless app.
+        expectedLoginResult: () => testSubjects.waitForEnabled('testEndpointsAuthenticationApp'),
+      });
+      expect(parse(await browser.getCurrentUrl()).pathname).to.eql('/authentication/app');
     });
 
     it('should show toast with error if SSO fails', async () => {