diff --git a/x-pack/test/functional/page_objects/security_page.ts b/x-pack/test/functional/page_objects/security_page.ts
index 081bd9f297503..5b0a9a679840a 100644
--- a/x-pack/test/functional/page_objects/security_page.ts
+++ b/x-pack/test/functional/page_objects/security_page.ts
@@ -168,7 +168,7 @@ export class SecurityPageObject extends FtrService {
     );
   }
 
-  private async isLoginFormVisible() {
+  public async isLoginFormVisible() {
     return await this.testSubjects.exists('loginForm');
   }
 
@@ -323,7 +323,14 @@ export class SecurityPageObject extends FtrService {
         if (alert?.accept) {
           await alert.accept();
         }
-        return !(await this.browser.getCurrentUrl()).includes('/logout');
+
+        if (this.config.get('serverless')) {
+          // Logout might trigger multiple redirects, but in the end we expect the Cloud login page
+          this.log.debug('Wait 5 sec for Cloud login page to be displayed');
+          return await this.find.existsByDisplayedByCssSelector('.login-form-password', 5000);
+        } else {
+          return !(await this.browser.getCurrentUrl()).includes('/logout');
+        }
       });
     }
   }
diff --git a/x-pack/test_serverless/functional/page_objects/svl_common_page.ts b/x-pack/test_serverless/functional/page_objects/svl_common_page.ts
index cf96bfd274eb9..7762bf92d046a 100644
--- a/x-pack/test_serverless/functional/page_objects/svl_common_page.ts
+++ b/x-pack/test_serverless/functional/page_objects/svl_common_page.ts
@@ -10,16 +10,90 @@ import { FtrProviderContext } from '../ftr_provider_context';
 export function SvlCommonPageProvider({ getService, getPageObjects }: FtrProviderContext) {
   const testSubjects = getService('testSubjects');
   const config = getService('config');
-  const pageObjects = getPageObjects(['security']);
+  const pageObjects = getPageObjects(['security', 'common']);
+  const retry = getService('retry');
+  const deployment = getService('deployment');
+  const log = getService('log');
+  const browser = getService('browser');
+
+  const delay = (ms: number) =>
+    new Promise((resolve) => {
+      setTimeout(resolve, ms);
+    });
 
   return {
+    async navigateToLoginForm() {
+      const url = deployment.getHostPort() + '/login';
+      await browser.get(url);
+      // ensure welcome screen won't be shown. This is relevant for environments which don't allow
+      // to use the yml setting, e.g. cloud
+      await browser.setLocalStorageItem('home:welcome:show', 'false');
+
+      log.debug('Waiting for Login Form to appear.');
+      await retry.waitForWithTimeout('login form', 10_000, async () => {
+        return await pageObjects.security.isLoginFormVisible();
+      });
+    },
+
     async login() {
       await pageObjects.security.forceLogout({ waitForLoginPage: false });
-      return await pageObjects.security.login(config.get('servers.kibana.username'));
+
+      // adding sleep to settle down logout
+      await pageObjects.common.sleep(2500);
+
+      await retry.waitForWithTimeout(
+        'Waiting for successful authentication',
+        90_000,
+        async () => {
+          if (!(await testSubjects.exists('loginUsername', { timeout: 1000 }))) {
+            await this.navigateToLoginForm();
+
+            await testSubjects.setValue('loginUsername', config.get('servers.kibana.username'));
+            await testSubjects.setValue('loginPassword', config.get('servers.kibana.password'));
+            await testSubjects.click('loginSubmit');
+          }
+
+          if (await testSubjects.exists('userMenuButton', { timeout: 10_000 })) {
+            log.debug('userMenuButton is found, logged in passed');
+            return true;
+          } else {
+            throw new Error(`Failed to login to Kibana via UI`);
+          }
+        },
+        async () => {
+          // Sometimes authentication fails and user is redirected to Cloud login page
+          // [plugins.security.authentication] Authentication attempt failed: UNEXPECTED_SESSION_ERROR
+          const currentUrl = await browser.getCurrentUrl();
+          if (currentUrl.startsWith('https://cloud.elastic.co')) {
+            log.debug(
+              'Probably authentication attempt failed, we are at Cloud login page. Retrying from scratch'
+            );
+          } else {
+            const authError = await testSubjects.exists('promptPage', { timeout: 2500 });
+            if (authError) {
+              log.debug('Probably SAML callback page, doing logout again');
+              await pageObjects.security.forceLogout({ waitForLoginPage: false });
+            } else {
+              const isOnLoginPage = await testSubjects.exists('loginUsername', { timeout: 1000 });
+              if (isOnLoginPage) {
+                log.debug(
+                  'Probably ES user profile activation failed, waiting 2 seconds and pressing Login button again'
+                );
+                await delay(2000);
+                await testSubjects.click('loginSubmit');
+              } else {
+                log.debug('New behaviour, trying to navigate and login again');
+              }
+            }
+          }
+        }
+      );
+      log.debug('Logged in successfully');
     },
 
     async forceLogout() {
       await pageObjects.security.forceLogout({ waitForLoginPage: false });
+      log.debug('Logged out successfully');
     },
 
     async assertProjectHeaderExists() {