reverted:
--- b/core/modules/contextual/js/toolbar/views/AuralView.js
+++ a/core/modules/contextual/js/toolbar/views/AuralView.js
@@ -55,11 +55,8 @@
       var tabbingContext = this.model.get('tabbingContext');
       // Always release an existing tabbing context.
       if (tabbingContext) {
-        // Only announce release when the context was active.
-        if (tabbingContext.active) {
-          Drupal.announce(this.options.strings.tabbingReleased);
-        }
         tabbingContext.release();
+        Drupal.announce(this.options.strings.tabbingReleased);
       }
       // Create a new tabbing context when edit mode is enabled.
       if (!this.model.get('isViewing')) {
reverted:
--- b/core/modules/contextual/tests/src/FunctionalJavascript/EditModeTest.php
+++ /dev/null
@@ -1,97 +0,0 @@
-<?php
-
-namespace Drupal\Tests\contextual\FunctionalJavascript;
-
-use Drupal\FunctionalJavascriptTests\JavascriptTestBase;
-
-/**
- * Tests edit mode.
- *
- * @group contextual
- */
-class EditModeTest extends JavascriptTestBase {
-
-  const ANNOUNCE_SELECTOR = '#drupal-live-announce';
-
-  const EDIT_BUTTON_SELECTOR = '#toolbar-bar div.contextual-toolbar-tab button';
-
-  /**
-   * {@inheritdoc}
-   */
-  public static $modules = [
-    'node',
-    'block',
-    'user',
-    'system',
-    'breakpoint',
-    'toolbar',
-    'contextual',
-  ];
-
-  /**
-   * {@inheritdoc}
-   */
-  protected function setUp() {
-    parent::setUp();
-    $user = $this->createUser([
-      'administer blocks',
-      'access contextual links',
-      'access toolbar',
-    ]);
-    $this->drupalLogin($user);
-    $this->placeBlock('system_powered_by_block', ['id' => 'powered']);
-  }
-
-  /**
-   * Test Drupal.announce messages appear.
-   */
-  public function testAnnounceEditMode() {
-    $web_assert = $this->assertSession();
-    $this->drupalGet('user');
-
-    // After the page loaded we need to additionally wait until the settings
-    // tray Ajax activity is done.
-    $web_assert->assertWaitOnAjaxRequest();
-
-    $this->pressToolbarEditButton();
-    $this->assertAnnounceEditMode();
-    $this->pressToolbarEditButton();
-    $this->assertAnnounceLeaveEditMode();
-    $this->pressToolbarEditButton();
-    $this->assertAnnounceEditMode();
-  }
-
-  /**
-   * Press the toolbar edit mode.
-   */
-  protected function pressToolbarEditButton() {
-    $edit_button = $this->getSession()->getPage()->find('css', static::EDIT_BUTTON_SELECTOR);
-    $edit_button->press();
-  }
-
-  /**
-   * Assert that the correct message was announced when entering edit mode.
-   */
-  protected function assertAnnounceEditMode() {
-    $web_assert = $this->assertSession();
-    // Wait for contextual trigger button.
-    $web_assert->waitForElementVisible('css', '.contextual trigger');
-    $web_assert->elementContains('css', static::ANNOUNCE_SELECTOR, 'Tabbing is constrained to a set of');
-    $web_assert->elementNotContains('css', static::ANNOUNCE_SELECTOR, 'Tabbing is no longer constrained by the Contextual module.');
-  }
-
-  /**
-   * Assert that the correct message was announced when leaving edit mode.
-   */
-  protected function assertAnnounceLeaveEditMode() {
-    $web_assert = $this->assertSession();
-    $page = $this->getSession()->getPage();
-    // Wait till all the contextual links are hidden.
-    $page->waitFor(1, function () use ($page, $web_assert) {
-      return empty($page->find('css', '.contextual .trigger.visually-hidden'));
-    });
-    $web_assert->elementContains('css', static::ANNOUNCE_SELECTOR, 'Tabbing is no longer constrained by the Contextual module.');
-    $web_assert->elementNotContains('css', static::ANNOUNCE_SELECTOR, 'Tabbing is constrained to a set of');
-  }
-
-}
only in patch2:
unchanged:
--- a/core/modules/contextual/tests/src/FunctionalJavascript/EditModeTest.php
+++ b/core/modules/contextual/tests/src/FunctionalJavascript/EditModeTest.php
@@ -53,11 +53,16 @@ public function testAnnounceEditMode() {
     // tray Ajax activity is done.
     $web_assert->assertWaitOnAjaxRequest();
 
+    // Enable edit mode.
     $this->pressToolbarEditButton();
     $this->assertAnnounceEditMode();
+    // Disable edit mode.
     $this->pressToolbarEditButton();
     $this->assertAnnounceLeaveEditMode();
+    // Enable edit mode again.
     $this->pressToolbarEditButton();
+    // Finally assert that the 'edit mode enabled' announcement is still correct
+    // after toggling the edit mode at least once.
     $this->assertAnnounceEditMode();
   }