diff --git a/darwin/dataset/remote_dataset_v2.py b/darwin/dataset/remote_dataset_v2.py
index b55d60d6d..ce94c4985 100644
--- a/darwin/dataset/remote_dataset_v2.py
+++ b/darwin/dataset/remote_dataset_v2.py
@@ -986,6 +986,8 @@ def _find_files_to_upload_as_single_file_items(
                 local_path = str(
                     found_file.relative_to(source_files[0]).parent.as_posix()
                 )
+                if local_path == ".":
+                    local_path = "/"
         uploading_files.append(
             LocalFile(
                 found_file,
diff --git a/tests/darwin/dataset/remote_dataset_test.py b/tests/darwin/dataset/remote_dataset_test.py
index a69aa65d0..01707996c 100644
--- a/tests/darwin/dataset/remote_dataset_test.py
+++ b/tests/darwin/dataset/remote_dataset_test.py
@@ -22,6 +22,7 @@
 from darwin.dataset.release import Release, ReleaseStatus
 from darwin.dataset.remote_dataset_v2 import (
     RemoteDatasetV2,
+    _find_files_to_upload_as_single_file_items,
     _find_files_to_upload_as_multi_file_items,
 )
 from darwin.dataset.upload_manager import (
@@ -846,6 +847,24 @@ def test_raises_if_incompatible_args_with_item_merge_mode(
                     **args,  # type: ignore
                 )
 
+    @pytest.mark.usefixtures("setup_zip")
+    def test_files_in_root_push_directoies_are_given_correct_remote_path(
+        self, setup_zip
+    ):
+        directory = setup_zip / "push_test_dir" / "topdir" / "subdir_1"
+        local_files = _find_files_to_upload_as_single_file_items(
+            [directory],
+            [],
+            [],
+            path="",
+            fps=1,
+            as_frames=False,
+            extract_views=False,
+            preserve_folders=True,
+        )
+        assert local_files[0].data["path"] == "/"
+        assert local_files[1].data["path"] == "/"
+
 
 @pytest.mark.usefixtures("setup_zip")
 class TestPushMultiSlotItem: