diff --git a/x-pack/test/functional/apps/upgrade_assistant/upgrade_assistant.ts b/x-pack/test/functional/apps/upgrade_assistant/upgrade_assistant.ts
index 57b8fb23613b..9e742ca5463a 100644
--- a/x-pack/test/functional/apps/upgrade_assistant/upgrade_assistant.ts
+++ b/x-pack/test/functional/apps/upgrade_assistant/upgrade_assistant.ts
@@ -4,6 +4,7 @@
  * you may not use this file except in compliance with the Elastic License.
  */
 
+import expect from '@kbn/expect';
 import { FtrProviderContext } from '../../ftr_provider_context';
 
 export default function upgradeAssistantFunctionalTests({
@@ -14,6 +15,7 @@ export default function upgradeAssistantFunctionalTests({
   const PageObjects = getPageObjects(['upgradeAssistant', 'common']);
   const security = getService('security');
   const log = getService('log');
+  const retry = getService('retry');
 
   describe('Upgrade Checkup', function () {
     this.tags('includeFirefox');
@@ -24,41 +26,52 @@ export default function upgradeAssistantFunctionalTests({
     });
 
     after(async () => {
-      await PageObjects.upgradeAssistant.expectTelemetryHasFinish();
+      await PageObjects.upgradeAssistant.waitForTelemetryHidden();
       await esArchiver.unload('empty_kibana');
       await security.testUser.restoreDefaults();
     });
 
     it('allows user to navigate to upgrade checkup', async () => {
       await PageObjects.upgradeAssistant.navigateToPage();
-      await PageObjects.upgradeAssistant.expectUpgradeAssistant();
     });
 
     it('allows user to toggle deprecation logging', async () => {
-      await PageObjects.upgradeAssistant.navigateToPage();
       log.debug('expect initial state to be ON');
-      await PageObjects.upgradeAssistant.expectDeprecationLoggingLabel('On');
-      log.debug('Now toggle to off');
-      await PageObjects.upgradeAssistant.toggleDeprecationLogging();
-      await PageObjects.common.sleep(2000);
-      log.debug('expect state to be OFF after toggle');
-      await PageObjects.upgradeAssistant.expectDeprecationLoggingLabel('Off');
-      await PageObjects.upgradeAssistant.toggleDeprecationLogging();
-      await PageObjects.common.sleep(2000);
-      log.debug('expect state to be ON after toggle');
-      await PageObjects.upgradeAssistant.expectDeprecationLoggingLabel('On');
+      expect(await PageObjects.upgradeAssistant.deprecationLoggingEnabledLabel()).to.be('On');
+      expect(await PageObjects.upgradeAssistant.isDeprecationLoggingEnabled()).to.be(true);
+
+      await retry.try(async () => {
+        log.debug('Now toggle to off');
+        await PageObjects.upgradeAssistant.toggleDeprecationLogging();
+
+        log.debug('expect state to be OFF after toggle');
+        expect(await PageObjects.upgradeAssistant.isDeprecationLoggingEnabled()).to.be(false);
+        expect(await PageObjects.upgradeAssistant.deprecationLoggingEnabledLabel()).to.be('Off');
+      });
+
+      log.debug('Now toggle back on.');
+      await retry.try(async () => {
+        await PageObjects.upgradeAssistant.toggleDeprecationLogging();
+        log.debug('expect state to be ON after toggle');
+        expect(await PageObjects.upgradeAssistant.isDeprecationLoggingEnabled()).to.be(true);
+        expect(await PageObjects.upgradeAssistant.deprecationLoggingEnabledLabel()).to.be('On');
+      });
     });
 
     it('allows user to open cluster tab', async () => {
       await PageObjects.upgradeAssistant.navigateToPage();
       await PageObjects.upgradeAssistant.clickTab('cluster');
-      await PageObjects.upgradeAssistant.expectIssueSummary('You have no cluster issues.');
+      expect(await PageObjects.upgradeAssistant.issueSummaryText()).to.be(
+        'You have no cluster issues.'
+      );
     });
 
     it('allows user to open indices tab', async () => {
       await PageObjects.upgradeAssistant.navigateToPage();
       await PageObjects.upgradeAssistant.clickTab('indices');
-      await PageObjects.upgradeAssistant.expectIssueSummary('You have no index issues.');
+      expect(await PageObjects.upgradeAssistant.issueSummaryText()).to.be(
+        'You have no index issues.'
+      );
     });
   });
 }
diff --git a/x-pack/test/functional/page_objects/upgrade_assistant_page.ts b/x-pack/test/functional/page_objects/upgrade_assistant_page.ts
index 3fe60747505a..739b796c5a62 100644
--- a/x-pack/test/functional/page_objects/upgrade_assistant_page.ts
+++ b/x-pack/test/functional/page_objects/upgrade_assistant_page.ts
@@ -4,7 +4,6 @@
  * you may not use this file except in compliance with the Elastic License.
  */
 
-import expect from '@kbn/expect';
 import { FtrProviderContext } from '../ftr_provider_context';
 
 export function UpgradeAssistantPageProvider({ getPageObjects, getService }: FtrProviderContext) {
@@ -24,34 +23,32 @@ export function UpgradeAssistantPageProvider({ getPageObjects, getService }: Ftr
       return await retry.try(async () => {
         await common.navigateToApp('settings');
         await testSubjects.click('upgrade_assistant');
-      });
-    }
-
-    async expectUpgradeAssistant() {
-      return await retry.try(async () => {
-        log.debug(`expectUpgradeAssistant()`);
-        expect(await testSubjects.exists('upgradeAssistantRoot')).to.equal(true);
-        const url = await browser.getCurrentUrl();
-        expect(url).to.contain(`/upgrade_assistant`);
+        retry.waitFor('url to contain /upgrade_assistant', async () => {
+          const url = await browser.getCurrentUrl();
+          return url.includes('/upgrade_assistant');
+        });
       });
     }
 
     async toggleDeprecationLogging() {
-      return await retry.try(async () => {
-        log.debug('toggleDeprecationLogging()');
-        await testSubjects.click('upgradeAssistantDeprecationToggle');
-      });
+      log.debug('toggleDeprecationLogging()');
+      await testSubjects.click('upgradeAssistantDeprecationToggle');
     }
 
-    async expectDeprecationLoggingLabel(labelText: string) {
-      return await retry.try(async () => {
-        log.debug('expectDeprecationLoggingLabel()');
-        const label = await find.byCssSelector(
-          '[data-test-subj="upgradeAssistantDeprecationToggle"] ~ span'
-        );
-        const value = await label.getVisibleText();
-        expect(value).to.equal(labelText);
-      });
+    async isDeprecationLoggingEnabled() {
+      const isDeprecationEnabled = await testSubjects.getAttribute(
+        'upgradeAssistantDeprecationToggle',
+        'aria-checked'
+      );
+      log.debug(`Deprecation enabled == ${isDeprecationEnabled}`);
+      return isDeprecationEnabled === 'true';
+    }
+
+    async deprecationLoggingEnabledLabel() {
+      const loggingEnabledLabel = await find.byCssSelector(
+        '[data-test-subj="upgradeAssistantDeprecationToggle"] ~ span'
+      );
+      return await loggingEnabledLabel.getVisibleText();
     }
 
     async clickTab(tabId: string) {
@@ -61,22 +58,20 @@ export function UpgradeAssistantPageProvider({ getPageObjects, getService }: Ftr
       });
     }
 
-    async expectIssueSummary(summary: string) {
-      return await retry.try(async () => {
-        log.debug('expectIssueSummary()');
-        const summaryElText = await testSubjects.getVisibleText('upgradeAssistantIssueSummary');
-        expect(summaryElText).to.eql(summary);
+    async waitForTelemetryHidden() {
+      const self = this;
+      retry.waitFor('Telemetry to disappear.', async () => {
+        return (await self.isTelemetryExists()) === false;
       });
     }
 
-    async expectTelemetryHasFinish() {
-      return await retry.try(async () => {
-        log.debug('expectTelemetryHasFinish');
-        const isTelemetryFinished = !(await testSubjects.exists(
-          'upgradeAssistantTelemetryRunning'
-        ));
-        expect(isTelemetryFinished).to.equal(true);
-      });
+    async issueSummaryText() {
+      log.debug('expectIssueSummary()');
+      return await testSubjects.getVisibleText('upgradeAssistantIssueSummary');
+    }
+
+    async isTelemetryExists() {
+      return await testSubjects.exists('upgradeAssistantTelemetryRunning');
     }
   }