diff --git a/lib/src/service/internal_key_event_handlers/enter_without_shift_in_text_node_handler.dart b/lib/src/service/internal_key_event_handlers/enter_without_shift_in_text_node_handler.dart
index 69c041007..e62d8e39d 100644
--- a/lib/src/service/internal_key_event_handlers/enter_without_shift_in_text_node_handler.dart
+++ b/lib/src/service/internal_key_event_handlers/enter_without_shift_in_text_node_handler.dart
@@ -77,15 +77,27 @@ ShortcutEventHandler enterWithoutShiftInTextNodesHandler =
   //  insert a empty text node before.
   if (selection.isCollapsed && selection.start.offset == 0) {
     if (textNode.toPlainText().isEmpty && textNode.subtype != null) {
+      final path =
+          textNode.path.length > 1 ? [++textNode.path.first] : textNode.path;
+
       final afterSelection = Selection.collapsed(
-        Position(path: textNode.path, offset: 0),
+        Position(path: path, offset: 0),
       );
-      final transaction = editorState.transaction
-        ..updateNode(textNode, {
-          BuiltInAttributeKey.subtype: null,
-          textNode.subtype!: null,
-        })
-        ..afterSelection = afterSelection;
+
+      final transaction = editorState.transaction;
+      if (textNode.path.length > 1) {
+        transaction
+          ..deleteNode(textNode)
+          ..insertNode(path, textNode)
+          ..afterSelection = afterSelection;
+      } else {
+        transaction
+          ..updateNode(textNode, {
+            BuiltInAttributeKey.subtype: null,
+            textNode.subtype!: null,
+          })
+          ..afterSelection = afterSelection;
+      }
       editorState.apply(transaction);
 
       final nextNode = textNode.next;
diff --git a/test/service/internal_key_event_handlers/enter_without_shift_in_text_node_handler_test.dart b/test/service/internal_key_event_handlers/enter_without_shift_in_text_node_handler_test.dart
index 5b7e8d84f..74605f86c 100644
--- a/test/service/internal_key_event_handlers/enter_without_shift_in_text_node_handler_test.dart
+++ b/test/service/internal_key_event_handlers/enter_without_shift_in_text_node_handler_test.dart
@@ -102,12 +102,23 @@ void main() async {
     testWidgets('Presses enter key in bulleted list', (tester) async {
       await _testStyleNeedToBeCopy(tester, BuiltInAttributeKey.bulletedList);
     });
+
     testWidgets('Presses enter key in numbered list', (tester) async {
       await _testStyleNeedToBeCopy(tester, BuiltInAttributeKey.numberList);
     });
+
     testWidgets('Presses enter key in checkbox styled text', (tester) async {
       await _testStyleNeedToBeCopy(tester, BuiltInAttributeKey.checkbox);
     });
+
+    testWidgets('Presses enter key in checkbox list indented', (tester) async {
+      await _testListOutdent(tester, BuiltInAttributeKey.checkbox);
+    });
+
+    testWidgets('Presses enter key in bulleted list indented', (tester) async {
+      await _testListOutdent(tester, BuiltInAttributeKey.bulletedList);
+    });
+
     testWidgets('Presses enter key in quoted text', (tester) async {
       await _testStyleNeedToBeCopy(tester, BuiltInAttributeKey.quote);
     });
@@ -203,6 +214,50 @@ Future<void> _testStyleNeedToBeCopy(WidgetTester tester, String style) async {
   }
 }
 
+Future<void> _testListOutdent(WidgetTester tester, String style) async {
+  const text = 'Welcome to Appflowy 😁';
+  final Attributes attributes = {
+    BuiltInAttributeKey.subtype: style,
+    style: true,
+  };
+
+  final editor = tester.editor
+    ..insertTextNode(text)
+    ..insertTextNode(text, attributes: attributes)
+    ..insertTextNode('', attributes: attributes);
+
+  await editor.startTesting();
+  await editor.updateSelection(
+    Selection.single(path: [2], startOffset: 0),
+  );
+  await editor.pressLogicKey(
+    key: LogicalKeyboardKey.tab,
+  );
+  expect(
+    editor.documentSelection,
+    Selection.single(path: [1, 0], startOffset: 0),
+  );
+
+  await editor.pressLogicKey(
+    key: LogicalKeyboardKey.enter,
+  );
+  expect(
+    editor.documentSelection,
+    Selection.single(path: [2], startOffset: 0),
+  );
+  expect(editor.nodeAtPath([2])?.subtype, style);
+
+  await editor.pressLogicKey(
+    key: LogicalKeyboardKey.enter,
+  );
+  expect(
+    editor.documentSelection,
+    Selection.single(path: [2], startOffset: 0),
+  );
+
+  expect(editor.nodeAtPath([2])?.subtype, null);
+}
+
 Future<void> _testMultipleSelection(
   WidgetTester tester,
   bool isBackwardSelection,