diff --git a/addons/web_editor/static/src/js/editor/snippets.editor.js b/addons/web_editor/static/src/js/editor/snippets.editor.js
index 340aed502f8..deeec7a9c79 100644
--- a/addons/web_editor/static/src/js/editor/snippets.editor.js
+++ b/addons/web_editor/static/src/js/editor/snippets.editor.js
@@ -2214,7 +2214,7 @@ var SnippetsMenu = Widget.extend({
             }).parent().addClass('o_default_snippet_text');
     },
     /**
-     * Changes the content of the left panel and selects a tab.
+     * Changes the content of the right panel and selects a tab.
      *
      * @private
      * @param {htmlString | Element | Text | Array | jQuery} [content]
diff --git a/addons/web_editor/static/src/js/editor/snippets.options.js b/addons/web_editor/static/src/js/editor/snippets.options.js
index fd9e1dbe725..fd5560d1374 100644
--- a/addons/web_editor/static/src/js/editor/snippets.options.js
+++ b/addons/web_editor/static/src/js/editor/snippets.options.js
@@ -3408,7 +3408,6 @@ const ImageHandlerOption = SnippetOptionWidget.extend({
         await this._rerenderXML();
         this._getImg().dataset.resizeWidth = this.optimizedWidth;
         await this._applyOptions();
-        await this.updateUI();
     },
     /**
      * Returns the image that is currently being modified.
@@ -3491,6 +3490,8 @@ registry.ImageOptimize = ImageHandlerOption.extend({
     async _onImageChanged(ev) {
         this.trigger_up('snippet_edition_request', {exec: async () => {
             await this._autoOptimizeImage();
+            await this.updateChangesInWysiwyg();
+            await this.updateUI();
             this.trigger_up('cover_update');
         }});
     },
diff --git a/addons/web_editor/static/src/js/wysiwyg/wysiwyg.js b/addons/web_editor/static/src/js/wysiwyg/wysiwyg.js
index c62fadfd4af..586a26b8478 100644
--- a/addons/web_editor/static/src/js/wysiwyg/wysiwyg.js
+++ b/addons/web_editor/static/src/js/wysiwyg/wysiwyg.js
@@ -715,10 +715,12 @@ var Wysiwyg = Widget.extend({
         const node = nodes[0];
         let $baseNode;
 
-        if (nodes.length === 1){
+        if (nodes.length === 1) {
             if (node instanceof JWEditorLib.FontAwesomeNode || node instanceof JWEditorLib.OdooVideoNode) {
-                const $originalDomNode = this.editorHelpers.getDomNodes(node).filter(dom => dom.nodeType === Node.ELEMENT_NODE);
-                $baseNode = $($originalDomNode).clone();
+                const originalDomNode = this.editorHelpers.getDomNodes(node).filter(dom => dom.nodeType === Node.ELEMENT_NODE);
+                $baseNode = $(originalDomNode).clone();
+            } else if (node instanceof JWEditorLib.ImageNode) {
+                $baseNode = $(this.editorHelpers.getDomNodes(node).filter(dom => dom.nodeType === Node.ELEMENT_NODE));
             }
             if (node instanceof JWEditorLib.FontAwesomeNode) {
                 params.htmlClass = [...$baseNode[0].classList].filter((className) => {
@@ -733,8 +735,13 @@ var Wysiwyg = Widget.extend({
         let mediaDialog = new weWidgets.MediaDialog(this, params, $baseNode);
         mediaDialog.open();
         mediaDialog.on('save', this, async (element) => {
-            if (params.htmlClass) element.className += " " + params.htmlClass;
-            return this.editor.execCommand('insertMedia', { element: element });
+            // If we're not _replacing_ a media (done by media dialog), insert it.
+            if (!$baseNode || $baseNode.length !== 1 || !$(element).is($baseNode[0].nodeName)) {
+                if (params.htmlClass) {
+                    element.className += " " + params.htmlClass;
+                }
+                await this.editor.execCommand('insertMedia', { element: element });
+            }
         });
     },
     async saveContent(context = this.editor) {