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 b9e00d5f544..3ee8ffab55f 100644
--- a/addons/web_editor/static/src/js/wysiwyg/widgets/link.js
+++ b/addons/web_editor/static/src/js/wysiwyg/widgets/link.js
@@ -59,6 +59,7 @@ const Link = Widget.extend({
             range.selectNodeContents(link);
             this.data.range = range;
             this.$link = $(link);
+            this.linkEl = link;
         } else {
             const selection = editable && editable.ownerDocument.getSelection();
             this.data.range = selection && selection.rangeCount && selection.getRangeAt(0);
@@ -66,6 +67,7 @@ const Link = Widget.extend({
 
         if (this.data.range) {
             this.$link = this.$link || $(OdooEditorLib.getInSelection(this.editable.ownerDocument, 'a'));
+            this.linkEl = this.$link[0];
             this.data.iniClassName = this.$link.attr('class') || '';
             this.colorCombinationClass = false;
             let $node = this.$link;
@@ -88,6 +90,10 @@ const Link = Widget.extend({
             this.data.content = this.data.content ? this.data.content.replace(/[ \t\r\n]+/g, ' ') : '';
         }
 
+        if (this.linkEl) {
+            this.data.isNewWindow = this.data.isNewWindow || this.linkEl.target === '_blank';
+        }
+
         const allBtnClassSuffixes = /(^|\s+)btn(-[a-z0-9_-]*)?/gi;
         const allBtnShapes = /\s*(rounded-circle|flat)\s*/gi;
         this.data.className = this.data.iniClassName
diff --git a/addons/web_editor/static/src/xml/wysiwyg.xml b/addons/web_editor/static/src/xml/wysiwyg.xml
index beadeffd48a..e63120f427d 100644
--- a/addons/web_editor/static/src/xml/wysiwyg.xml
+++ b/addons/web_editor/static/src/xml/wysiwyg.xml
@@ -641,7 +641,7 @@
             </we-select>
         </we-row>
         <we-row  t-if="!widget.isButton &amp;&amp; !widget.options.forceNewWindow">
-            <we-button class="o_we_user_value_widget o_we_checkbox_wrapper">
+            <we-button t-attf-class="o_we_user_value_widget o_we_checkbox_wrapper #{widget.data.isNewWindow ? 'active' : ''}">
                 <we-title class="o_long_title">⌙ Open in new window</we-title>
                     <div class="o_switch">
                         <we-checkbox name="is_new_window" t-att-checked="widget.data.isNewWindow ? 'checked' : undefined"/>