diff --git a/frontend/app_flowy/packages/flowy_editor/lib/operation/operation.dart b/frontend/app_flowy/packages/flowy_editor/lib/operation/operation.dart
index 487844af14..eafa4a31da 100644
--- a/frontend/app_flowy/packages/flowy_editor/lib/operation/operation.dart
+++ b/frontend/app_flowy/packages/flowy_editor/lib/operation/operation.dart
@@ -128,6 +128,8 @@ Path transformPath(Path preInsertPath, Path b, [int delta = 1]) {
   final bAtIndex = b[preInsertPath.length - 1];
   if (preInsertLast <= bAtIndex) {
     prefix.add(bAtIndex + delta);
+  } else {
+    prefix.add(bAtIndex);
   }
   prefix.addAll(suffix);
   return prefix;
diff --git a/frontend/app_flowy/packages/flowy_editor/test/operation_test.dart b/frontend/app_flowy/packages/flowy_editor/test/operation_test.dart
index 683b6df58e..176f00b734 100644
--- a/frontend/app_flowy/packages/flowy_editor/test/operation_test.dart
+++ b/frontend/app_flowy/packages/flowy_editor/test/operation_test.dart
@@ -19,6 +19,7 @@ void main() {
     test("transform path not changed", () {
       expect(transformPath([0, 1, 2], [0, 0, 7, 8, 9]), [0, 0, 7, 8, 9]);
       expect(transformPath([0, 1, 2], [0, 1]), [0, 1]);
+      expect(transformPath([1, 1], [1, 0]), [1, 0]);
     });
     test("transform path delta", () {
       expect(transformPath([0, 1], [0, 1], 5), [0, 6]);