diff --git a/addons/web_editor/static/src/js/editor/summernote.js b/addons/web_editor/static/src/js/editor/summernote.js
index 06a282d0076..80ccd3d0c82 100644
--- a/addons/web_editor/static/src/js/editor/summernote.js
+++ b/addons/web_editor/static/src/js/editor/summernote.js
@@ -1792,6 +1792,7 @@ $.summernote.pluginEvents.indent = function (event, editor, layoutInfo, outdent)
     var flag = false;
     function indentUL(UL, start, end) {
         var next;
+        var previous;
         var tagName = UL.tagName;
         var node = UL.firstChild;
         var ul = document.createElement(tagName);
@@ -1808,7 +1809,15 @@ $.summernote.pluginEvents.indent = function (event, editor, layoutInfo, outdent)
         while (node) {
             if (flag === 1 || node === start || $.contains(node, start)) {
                 flag = true;
-                node.parentNode.insertBefore(li, node);
+                if (previous) {
+                    if (dom.isList(previous.lastChild)) {
+                        ul = previous.lastChild;
+                    } else {
+                        previous.appendChild(ul);
+                    }
+                } else {
+                    node.parentNode.insertBefore(li, node);
+                }
             }
             next = dom.nextElementSibling(node);
             if (flag) {
@@ -1818,6 +1827,7 @@ $.summernote.pluginEvents.indent = function (event, editor, layoutInfo, outdent)
                 flag = false;
                 break;
             }
+            previous = node;
             node = next;
         }
 
@@ -1855,14 +1865,22 @@ $.summernote.pluginEvents.indent = function (event, editor, layoutInfo, outdent)
             }
             next = dom.nextElementSibling(node);
             if (flag) {
+                var $succeeding = $(node).nextAll();
                 ul = node.parentNode;
-                li.parentNode.insertBefore(node, li);
+                if (dom.previousElementSibling(ul)) {
+                    dom.insertAfter(node, li);
+                } else {
+                    li.parentNode.insertBefore(node, li);
+                }
+                $succeeding.insertAfter(node);
                 if (!ul.children.length) {
-                    if (ul.parentNode.tagName === "LI") {
+                    if (ul.parentNode.tagName === "LI" && !dom.previousElementSibling(ul)) {
                         ul = ul.parentNode;
                     }
                     ul.parentNode.removeChild(ul);
                 }
+                flag = false;
+                break;
             }
 
             if (node === end || $.contains(node, end)) {
@@ -1894,9 +1912,13 @@ $.summernote.pluginEvents.indent = function (event, editor, layoutInfo, outdent)
     var $dom = $(ancestor);
 
     if (!dom.isList(ancestor)) {
-        // to indent a selection, we indent the child nodes of the common
-        // ancestor that contains this selection
-        $dom = $(dom.node(ancestor)).children();
+        if (dom.isList(ancestor.parentNode)) {
+            $dom = $(ancestor.parentNode);
+        } else {
+            // to indent a selection, we indent the child nodes of the common
+            // ancestor that contains this selection
+            $dom = $(dom.node(ancestor)).children();
+        }
     }
     if (!$dom.not('br').length) {
         // if selection is inside a list, we indent its list items