From 35e2fdc832a49b100f96e087fb40883c355cf54c Mon Sep 17 00:00:00 2001
From: ghzhost <patricknasci@ghzhost.com>
Date: Sun, 23 Aug 2026 14:17:26 +0000
Subject: [PATCH] fix(diagnostics): re-raise cleanup IO errors on directory
 removal instead of swallowing as retained

remove_cleanup previously caught a bare except OSError on rmdir(),
which caused any directory deletion failure (permissions, hardware IO error,
etc.) to be silently reclassified as an intentional retained entry.

Narrow the catch to errno.ENOTEMPTY and errno.EEXIST, and raise
ContextSafeError('cleanup_io_error', ...) for all other OSErrors, matching
the file unlink branch immediately below.

Fixes ChelseaKR/contextsafe#36.
---
 src/contextsafe/diagnostics.py | 11 ++++++++---
 tests/test_diagnostics.py      | 16 ++++++++++++++++
 2 files changed, 24 insertions(+), 3 deletions(-)

diff --git a/src/contextsafe/diagnostics.py b/src/contextsafe/diagnostics.py
index dd36cc8..8096e79 100644
--- a/src/contextsafe/diagnostics.py
+++ b/src/contextsafe/diagnostics.py
@@ -34,6 +34,7 @@
 
 from __future__ import annotations
 
+import errno
 import os
 import platform
 import sys
@@ -231,9 +232,13 @@ def remove_cleanup(plan: CleanupPlan) -> tuple[int, int]:
             # deleting the thing we just declined to delete.
             try:
                 target.rmdir()
-            except OSError:
-                retained += 1
-                continue
+            except OSError as exc:
+                if exc.errno in (errno.ENOTEMPTY, errno.EEXIST):
+                    retained += 1
+                    continue
+                raise ContextSafeError(
+                    "cleanup_io_error", "$", "a workspace entry could not be removed"
+                ) from exc
         else:
             try:
                 target.unlink()
diff --git a/tests/test_diagnostics.py b/tests/test_diagnostics.py
index 864ce30..8dada83 100644
--- a/tests/test_diagnostics.py
+++ b/tests/test_diagnostics.py
@@ -16,6 +16,7 @@
 
 from __future__ import annotations
 
+import errno
 import json
 import os
 import unicodedata
@@ -549,6 +550,21 @@ def refuse(self: Path, *args: Any, **kwargs: Any) -> None:
     assert excinfo.value.code == "cleanup_io_error"
 
 
+def test_removal_reports_a_directory_it_cannot_delete_for_non_empty_error(
+    monkeypatch: pytest.MonkeyPatch, populated_workspace: Path
+) -> None:
+    """A directory rmdir failure from permission/IO error raises cleanup_io_error."""
+
+    def refuse(self: Path, *args: Any, **kwargs: Any) -> None:
+        raise PermissionError(errno.EACCES, "Permission denied")
+
+    plan = enumerate_cleanup(populated_workspace)
+    monkeypatch.setattr(Path, "rmdir", refuse)
+    with pytest.raises(ContextSafeError) as excinfo:
+        remove_cleanup(plan)
+    assert excinfo.value.code == "cleanup_io_error"
+
+
 def test_an_unreadable_log_is_reported_not_overwritten(
     monkeypatch: pytest.MonkeyPatch, tmp_path: Path
 ) -> None: