diff --git a/addons/web_editor/static/lib/odoo-editor/src/OdooEditor.js b/addons/web_editor/static/lib/odoo-editor/src/OdooEditor.js
index ab4ba780854..1ee442858d7 100644
--- a/addons/web_editor/static/lib/odoo-editor/src/OdooEditor.js
+++ b/addons/web_editor/static/lib/odoo-editor/src/OdooEditor.js
@@ -209,6 +209,7 @@ export class OdooEditor extends EventTarget {
                         return closestElement(selection.anchorNode, 'P, DIV');
                     }
                 },
+                preHistoryUndo: () => {},
                 isHintBlacklisted: () => false,
                 filterMutationRecords: (records) => records,
                 direction: 'ltr',
@@ -809,6 +810,7 @@ export class OdooEditor extends EventTarget {
      * "consumed": The position has been undone and is considered consumed.
      */
     historyUndo() {
+        this.options.preHistoryUndo();
         // The last step is considered an uncommited draft so always revert it.
         const lastStep = this._currentStep;
         this.historyRevert(lastStep);
diff --git a/addons/web_editor/static/src/js/wysiwyg/widgets/link.js b/addons/web_editor/static/src/js/wysiwyg/widgets/link.js
index 6c00e81ba9c..0573494e273 100644
--- a/addons/web_editor/static/src/js/wysiwyg/widgets/link.js
+++ b/addons/web_editor/static/src/js/wysiwyg/widgets/link.js
@@ -19,6 +19,7 @@ const Link = Widget.extend({
         'input': '_onAnyChange',
         'change': '_onAnyChange',
         'input input[name="url"]': '_onURLInput',
+        'change input[name="url"]': '_onURLInputChange',
     },
 
     /**
@@ -142,6 +143,7 @@ const Link = Widget.extend({
             var match = /mailto:(.+)/.exec(this.data.url);
             this.$('input[name="url"]').val(match ? match[1] : this.data.url);
             this._onURLInput();
+            this._savedURLInputOnDestroy = false;
         }
 
         this._updateOptionsUI();
@@ -152,6 +154,15 @@ const Link = Widget.extend({
 
         return this._super.apply(this, arguments);
     },
+    /**
+     * @override
+     */
+    destroy () {
+        if (this._savedURLInputOnDestroy) {
+            this._adaptPreview();
+        }
+        this._super(...arguments);
+    },
 
     //--------------------------------------------------------------------------
     // Public
@@ -458,19 +469,26 @@ const Link = Widget.extend({
     /**
      * @private
      */
-    _onAnyChange: function () {
-        this._adaptPreview();
+    _onAnyChange: function (e) {
+        if (!e.target.closest('input[type="text"]')) {
+            this._adaptPreview();
+        }
     },
     /**
      * @private
      */
     _onURLInput: function () {
+        this._savedURLInputOnDestroy = true;
         var $linkUrlInput = this.$('#o_link_dialog_url_input');
         let value = $linkUrlInput.val();
         let isLink = value.indexOf('@') < 0;
         this.$('input[name="is_new_window"]').closest('.form-group').toggleClass('d-none', !isLink);
         this.$('.o_strip_domain').toggleClass('d-none', value.indexOf(window.location.origin) !== 0);
     },
+    _onURLInputChange: function () {
+        this._adaptPreview();
+        this._savedURLInputOnDestroy = false;
+    },
 });
 
 /**
diff --git a/addons/web_editor/static/src/js/wysiwyg/widgets/link_tools.js b/addons/web_editor/static/src/js/wysiwyg/widgets/link_tools.js
index e7abba60cf7..08631fcb1b8 100644
--- a/addons/web_editor/static/src/js/wysiwyg/widgets/link_tools.js
+++ b/addons/web_editor/static/src/js/wysiwyg/widgets/link_tools.js
@@ -45,31 +45,28 @@ const LinkTools = Link.extend({
      * @override
      */
     start: function () {
-        this.$link.addClass('oe_edited_link');
-        this.$button.addClass('active');
+        this._addHintClasses();
         return this._super(...arguments);
     },
     destroy: function () {
         if (!this.el) {
             return this._super(...arguments);
         }
-        $(this.options.wysiwyg.odooEditor.document).find('.oe_edited_link').removeClass('oe_edited_link');
         const $contents = this.$link.contents();
         if (!this.$link.attr('href') && !this.colorCombinationClass) {
             $contents.unwrap();
         }
-        this.$button.removeClass('active');
-        this.applyLinkToDom(this._getData());
-        if (!this.options.wysiwyg.odooEditor.isDestroyed) {
-            this.options.wysiwyg.odooEditor.historyStep();
-        }
         this._observer.disconnect();
         this._super(...arguments);
+        this._removeHintClasses();
     },
 
     applyLinkToDom() {
         this._observer.disconnect();
+        this._removeHintClasses();
         this._super(...arguments);
+        this.options.wysiwyg.odooEditor.historyStep();
+        this._addHintClasses();
         this._observer.observe(this._link, {subtree: true, childList: true, characterData: true});
     },
 
@@ -97,7 +94,6 @@ const LinkTools = Link.extend({
         if (data === null) {
             return;
         }
-        data.classes += ' oe_edited_link';
         this.applyLinkToDom(data);
     },
     /**
@@ -323,6 +319,24 @@ const LinkTools = Link.extend({
             $colorPreview.css('background-image', isColorGradient(color) ? color : '');
         }
     },
+    /**
+     * Add hint to the classes of the link and button.
+     */
+    _addHintClasses () {
+        this.options.wysiwyg.odooEditor.observerUnactive("hint_classes");
+        this.$link.addClass('oe_edited_link');
+        this.$button.addClass('active');
+        this.options.wysiwyg.odooEditor.observerActive("hint_classes");
+    },
+    /**
+     * Remove hint to the classes of the link and button.
+     */
+    _removeHintClasses () {
+        this.options.wysiwyg.odooEditor.observerUnactive("hint_classes");
+        $(this.options.wysiwyg.odooEditor.document).find('.oe_edited_link').removeClass('oe_edited_link');
+        this.$button.removeClass('active');
+        this.options.wysiwyg.odooEditor.observerActive("hint_classes");
+    },
 
     //--------------------------------------------------------------------------
     // Handlers
diff --git a/addons/web_editor/static/src/js/wysiwyg/wysiwyg.js b/addons/web_editor/static/src/js/wysiwyg/wysiwyg.js
index cadf73a20fe..10b8b95f5ed 100644
--- a/addons/web_editor/static/src/js/wysiwyg/wysiwyg.js
+++ b/addons/web_editor/static/src/js/wysiwyg/wysiwyg.js
@@ -163,6 +163,12 @@ const Wysiwyg = Widget.extend({
                     return !(record.target.classList && record.target.classList.contains('o_header_standard'));
                 });
             },
+            preHistoryUndo: () => {
+                if (this.linkTools) {
+                    this.linkTools.destroy();
+                    this.linkTools = undefined;
+                }
+            },
             commands: commands,
             plugins: options.editorPlugins,
             direction: localization.direction || 'ltr',