diff --git a/core/modules/outside_in/js/outside_in.es6.js b/core/modules/outside_in/js/outside_in.es6.js
index dc5d8852728..f36bb835f24 100644
--- a/core/modules/outside_in/js/outside_in.es6.js
+++ b/core/modules/outside_in/js/outside_in.es6.js
@@ -23,6 +23,14 @@
    * @listens event:drupalContextualLinkAdded
    */
   $(document).on('drupalContextualLinkAdded', (event, data) => {
+    // When the first contextual link is added to the page set Edit Mode.
+    $('body').once('outside_in.edit_mode_init').each(() => {
+      const editMode = localStorage.getItem('Drupal.contextualToolbar.isViewing') === 'false';
+      if (editMode) {
+        setEditModeState(true);
+      }
+    });
+
     // Bind Ajax behaviors to all items showing the class.
     // @todo Fix contextual links to work with use-ajax links in
     //    https://www.drupal.org/node/2764931.
@@ -183,23 +191,6 @@
     $('.edit-mode-inactive').toggleClass('visually-hidden', editMode);
   }
 
-  /**
-   * Attaches contextual's edit toolbar tab behavior.
-   *
-   * @type {Drupal~behavior}
-   *
-   * @prop {Drupal~behaviorAttach} attach
-   *   Attaches contextual toolbar behavior on a contextualToolbar-init event.
-   */
-  Drupal.behaviors.outsideInEdit = {
-    attach() {
-      const editMode = localStorage.getItem('Drupal.contextualToolbar.isViewing') === 'false';
-      if (editMode) {
-        setEditModeState(true);
-      }
-    },
-  };
-
   /**
    * Toggle the js-outside-edit-mode class on items that we want to disable while in edit mode.
    *
diff --git a/core/modules/outside_in/js/outside_in.js b/core/modules/outside_in/js/outside_in.js
index b97d9599189..dc949c7bd79 100644
--- a/core/modules/outside_in/js/outside_in.js
+++ b/core/modules/outside_in/js/outside_in.js
@@ -13,6 +13,13 @@
   var quickEditItemSelector = '[data-quickedit-entity-id]';
 
   $(document).on('drupalContextualLinkAdded', function (event, data) {
+    $('body').once('outside_in.edit_mode_init').each(function () {
+      var editMode = localStorage.getItem('Drupal.contextualToolbar.isViewing') === 'false';
+      if (editMode) {
+        setEditModeState(true);
+      }
+    });
+
     Drupal.attachBehaviors(data.$el[0]);
 
     data.$el.find(blockConfigureSelector).on('click.outsidein', function () {
@@ -112,15 +119,6 @@
     $('.edit-mode-inactive').toggleClass('visually-hidden', editMode);
   }
 
-  Drupal.behaviors.outsideInEdit = {
-    attach: function attach() {
-      var editMode = localStorage.getItem('Drupal.contextualToolbar.isViewing') === 'false';
-      if (editMode) {
-        setEditModeState(true);
-      }
-    }
-  };
-
   Drupal.behaviors.toggleEditMode = {
     attach: function attach() {
       $(toggleEditSelector).once('outsidein').on('click.outsidein', toggleEditMode);
diff --git a/core/modules/outside_in/tests/src/FunctionalJavascript/OutsideInBlockFormTest.php b/core/modules/outside_in/tests/src/FunctionalJavascript/OutsideInBlockFormTest.php
index 4e519f6f8b5..daf3d1f7378 100644
--- a/core/modules/outside_in/tests/src/FunctionalJavascript/OutsideInBlockFormTest.php
+++ b/core/modules/outside_in/tests/src/FunctionalJavascript/OutsideInBlockFormTest.php
@@ -238,6 +238,9 @@ class OutsideInBlockFormTest extends OutsideInJavascriptTestBase {
     // to open the off-canvas dialog in edit mode.
     $contextual_link = $this->assertSession()->waitForElement('css', "$contextual_link_container .contextual-links a");
     $this->assertNotEmpty($contextual_link);
+    // When page first loads Edit Mode is not triggered until first contextual
+    // link is added.
+    $this->assertElementVisibleAfterWait('css', '.dialog-off-canvas__main-canvas.js-outside-in-edit-mode');
     // Ensure that all other Ajax activity is completed.
     $this->assertSession()->assertWaitOnAjaxRequest();
     $this->click($block_selector);