diff -u b/core/modules/outside_in/js/outside_in.js b/core/modules/outside_in/js/outside_in.js
--- b/core/modules/outside_in/js/outside_in.js
+++ b/core/modules/outside_in/js/outside_in.js
@@ -10,6 +10,7 @@
   var blockConfigureSelector = '[data-dialog-renderer="offcanvas"]';
   var toggleEditSelector = '[data-drupal-outsidein="toggle"]';
   var itemsToToggleSelector = '#main-canvas, #toolbar-bar, [data-drupal-outsidein="editable"] a, [data-drupal-outsidein="editable"] button';
+  var contextualItemsSelector = '[data-contextual-id] a, [data-contextual-id] button';
 
   /**
    * Reacts to contextual links being added.
@@ -45,8 +46,7 @@
    *   Items that should be toggled.
    */
   function getItemsToToggle() {
-    return $(itemsToToggleSelector)
-      .not('[data-contextual-id] a, [data-contextual-id] button');
+    return $(itemsToToggleSelector).not(contextualItemsSelector);
   }
 
   /**
@@ -65,6 +65,10 @@
     setEditModeState(!isInEditMode());
   }
 
+  function preventClick(event) {
+    event.preventDefault();
+  }
+
   /**
    *  Helper to switch edit mode state.
    *
@@ -74,6 +78,7 @@
   function setEditModeState(editMode) {
     editMode = !!editMode;
     var $editButton = $(toggleEditSelector);
+    var $editables;
     // Turn on edit mode.
     if (editMode) {
       $editButton.text(Drupal.t('Editing'));
@@ -81,9 +86,34 @@
       if ($('#toolbar-item-administration-tray').hasClass('is-active')) {
         $('#toolbar-item-administration').trigger('click');
       }
+
+      $editables = $('[data-drupal-outsidein="editable"]').once('outsidein');
+      if ($editables.length) {
+        // Use event capture to prevent clicks on links.
+        document.addEventListener('click', preventClick, true);
+
+        // When a click occurs try and find the outside-in edit link
+        // and click it.
+        $editables
+          .not(contextualItemsSelector)
+          .on('click.outsidein', function (e) {
+            // @todo check if we can't use currentTarget too.
+            if ($(e.target).parent().hasClass('contextual') || !localStorage.getItem('Drupal.contextualToolbar.isViewing')) {
+              return;
+            }
+
+            $(e.currentTarget).find(blockConfigureSelector).trigger('click');
+          });
+      }
     }
     // Disable edit mode.
     else {
+      $editables = $('[data-drupal-outsidein="editable"]').removeOnce('outsidein');
+      if ($editables.length) {
+        document.removeEventListener('click', preventClick, true);
+        $editables.off('.outsidein');
+      }
+
       $editButton.text(Drupal.t('Edit'));
       // Close/remove offcanvas.
       $('.ui-dialog-offcanvas .ui-dialog-titlebar-close').trigger('click');
@@ -123,29 +153,4 @@
       $(toggleEditSelector).once('outsidein').on('click.outsidein', toggleEditMode);
 
-      var $editables = $('[data-drupal-outsidein="editable"]').once('outsidein');
-      if ($editables.length) {
-
-        // Bind an event listener to the editable div and stops default actions
-        // of those elements.
-        $editables.on('click.outsidein', '.js-outside-in-edit-mode', function (e) {
-          if (isInEditMode()) {
-            e.preventDefault();
-          }
-        });
-
-        // When a click occurs try and find the outside-in edit link
-        // and click it.
-        $editables
-          .not('[data-contextual-id] a, [data-contextual-id] button')
-          .on('click.outsidein', function (e) {
-            // @todo check if we can't use currentTarget too.
-            if ($(e.target).parent().hasClass('contextual') || !localStorage.getItem('Drupal.contextualToolbar.isViewing')) {
-              return;
-            }
-
-            $(e.currentTarget).find(blockConfigureSelector).trigger('click');
-          });
-      }
-
       var search = Drupal.ajax.WRAPPER_FORMAT + '=drupal_dialog';
       var replace = Drupal.ajax.WRAPPER_FORMAT + '=drupal_dialog_offcanvas';