diff --git a/addons/web_editor/static/src/js/wysiwyg/wysiwyg.js b/addons/web_editor/static/src/js/wysiwyg/wysiwyg.js
index 5bb6c8b4b7e..bfdea46b331 100644
--- a/addons/web_editor/static/src/js/wysiwyg/wysiwyg.js
+++ b/addons/web_editor/static/src/js/wysiwyg/wysiwyg.js
@@ -1356,6 +1356,11 @@ const Wysiwyg = Widget.extend({
         const field = $editable.data('oe-field');
         const type = $editable.data('oe-type');
 
+        // The html_field value should not be updated while the mediaDialog is
+        // in use because if its value change, restoreSelection may fail since
+        // it has a reference to HTMLElements which are not in the DOM anymore.
+        this._shouldDelayBlur = true;
+
         this.mediaDialogWrapper = new ComponentWrapper(this, MediaDialogWrapper, {
             resModel: model,
             resId: $editable.data('oe-id'),
@@ -2445,8 +2450,9 @@ const Wysiwyg = Widget.extend({
         if (!e.target.classList.contains('o_editable_date_field_linked')) {
             this.$editable.find('.o_editable_date_field_linked').removeClass('o_editable_date_field_linked');
         }
-        if (e.target.closest('.oe-toolbar')) {
-            this._onToolbar = true;
+        const closestDialog = e.target.closest('.o_dialog, .o_web_editor_dialog');
+        if (e.target.closest('.oe-toolbar') || (closestDialog && closestDialog.querySelector('.o_select_media_dialog, .o_link_dialog'))) {
+            this._shouldDelayBlur = true;
         } else {
             if (this._pendingBlur && !e.target.closest('.o_wysiwyg_wrapper')) {
                 // todo: to remove when removing the legacy field_html
@@ -2454,11 +2460,11 @@ const Wysiwyg = Widget.extend({
                 this.options.onWysiwygBlur && this.options.onWysiwygBlur();
                 this._pendingBlur = false;
             }
-            this._onToolbar = false;
+            this._shouldDelayBlur = false;
         }
     },
     _onBlur: function () {
-        if (this._onToolbar) {
+        if (this._shouldDelayBlur) {
             this._pendingBlur = true;
         } else {
             // todo: to remove when removing the legacy field_html