diff --git a/addons/web_editor/static/src/js/wysiwyg/plugin/keyboard.js b/addons/web_editor/static/src/js/wysiwyg/plugin/keyboard.js
index 3ab6a5f0317..94ec9306f7d 100644
--- a/addons/web_editor/static/src/js/wysiwyg/plugin/keyboard.js
+++ b/addons/web_editor/static/src/js/wysiwyg/plugin/keyboard.js
@@ -296,6 +296,7 @@ var KeyboardPlugin = AbstractPlugin.extend({
         var next = this.context.invoke('HelperPlugin.splitTree', ancestor, point, {
             isSkipPaddingBlankHTML: !this.context.invoke('HelperPlugin.isNodeBlockType', point.node.parentNode) && !!point.node.parentNode.nextSibling
         });
+        $(next).removeClass('o_checked');
         while (next.firstChild) {
             next = next.firstChild;
         }
diff --git a/addons/web_editor/static/tests/wysiwyg_keyboard_tests.js b/addons/web_editor/static/tests/wysiwyg_keyboard_tests.js
index 56ceb27a025..28a8106234c 100644
--- a/addons/web_editor/static/tests/wysiwyg_keyboard_tests.js
+++ b/addons/web_editor/static/tests/wysiwyg_keyboard_tests.js
@@ -1179,6 +1179,30 @@ var keyboardTestsEnter = [{
             start: "br->0",
         },
     },
+    {
+        name: "in ul.o_checklist > li.o_checked > p: ENTER at end",
+        content: '<ul class="o_checklist"><li class="o_checked"><p>test</p></li></ul>',
+        steps: [{
+            start: "p:contents()[0]->4",
+            key: 'ENTER',
+        }],
+        test: {
+            content: '<ul class="o_checklist"><li class="o_checked"><p>test</p></li><li><p><br></p></li></ul>',
+            start: "br->0",
+        },
+    },
+    {
+        name: "in ul.o_checklist > li.o_checked > p > b: ENTER within text",
+        content: '<ul class="o_checklist"><li class="o_checked"><p><b>test</b></p></li></ul>',
+        steps: [{
+            start: "b:contents()[0]->2",
+            key: 'ENTER',
+        }],
+        test: {
+            content: '<ul class="o_checklist"><li class="o_checked"><p><b>te</b></p></li><li><p><b>st</b></p></li></ul>',
+            start: "b:eq(1):contents()[0]->0",
+        },
+    },
 
     // end list UL / OL