checkout: ensure subdirs are deleted before parent dir (#601)

* checkout: ensure subdirs are deleted before parent dir

* Rename test function

Author: baleian

src/dvc_data/index/checkout.py

@@ -160,7 +160,8 @@ def _create_files(  # noqa: C901, PLR0912, PLR0913
 
 
 def _delete_dirs(entries, path, fs):
-    for entry in entries:
+    reversed_by_key = sorted(entries, key=lambda entry: entry.key, reverse=True)
+    for entry in reversed_by_key:
         try:
             fs.rmdir(fs.join(path, *entry.key))
         except OSError:

tests/index/test_checkout.py

@@ -103,3 +103,32 @@ def test_checkout_broken_dir(tmp_upath, odb, as_filesystem):
         (tmp_upath / "data" / "baz"),
     }
     assert not (tmp_upath / "broken").exists()
+
+
+def test_checkout_delete_nested_dir(tmp_upath, odb, as_filesystem):
+    old = DataIndex(
+        {
+            ("dir1",): DataIndexEntry(
+                key=("dir1",),
+                meta=Meta(isdir=True),
+            ),
+            ("dir1", "subdir1"): DataIndexEntry(
+                key=("dir1", "subdir1"),
+                meta=Meta(isdir=True),
+            ),
+        }
+    )
+    diff = compare(None, old)
+    apply(diff, str(tmp_upath), as_filesystem(tmp_upath.fs))
+
+    assert (tmp_upath / "dir1").exists()
+    assert (tmp_upath / "dir1").is_dir()
+    assert (tmp_upath / "dir1" / "subdir1").exists()
+    assert (tmp_upath / "dir1" / "subdir1").is_dir()
+
+    new = DataIndex({})
+    diff = compare(old, new, delete=True)
+    apply(diff, str(tmp_upath), as_filesystem(tmp_upath.fs))
+
+    assert not (tmp_upath / "dir1" / "subdir1").exists()
+    assert not (tmp_upath / "dir1").exists()