diff --git a/semantica/context/agent_memory.py b/semantica/context/agent_memory.py
index 5456e30c..2f2b8995 100644
--- a/semantica/context/agent_memory.py
+++ b/semantica/context/agent_memory.py
@@ -1867,10 +1867,19 @@ class AgentMemory:
                 try:
                     candidate_exists = candidate.exists()
                 except OSError as exc:
-                    raise OSError(
+                    error_message = (
                         "Failed to inspect possible Markdown import "
-                        f"path: {candidate}"
-                    ) from exc
+                        f"path {candidate}: {exc.strerror or str(exc)}"
+                    )
+                    if exc.errno is None:
+                        error = OSError(error_message)
+                    else:
+                        error = OSError(
+                            exc.errno,
+                            error_message,
+                            exc.filename or str(candidate),
+                        )
+                    raise error from exc
 
                 if candidate_exists:
                     documents = self._read_markdown_path(candidate)
diff --git a/tests/context/test_agent_memory_markdown.py b/tests/context/test_agent_memory_markdown.py
index 9bb6c290..fb9158ed 100644
--- a/tests/context/test_agent_memory_markdown.py
+++ b/tests/context/test_agent_memory_markdown.py
@@ -1,3 +1,4 @@
+import errno
 from copy import deepcopy
 from datetime import datetime, timedelta, timezone
 from unittest.mock import MagicMock, patch
@@ -676,18 +677,25 @@ def test_markdown_string_path_read_errors_are_not_treated_as_content(tmp_path):
 
 def test_markdown_string_path_inspection_errors_are_actionable():
     memory = AgentMemory()
+    original_error = PermissionError(
+        errno.EACCES,
+        "inspection denied",
+        "blocked-memory.md",
+    )
 
     with patch(
         "semantica.context.agent_memory.Path.exists",
-        side_effect=PermissionError("inspection denied"),
+        side_effect=original_error,
     ):
         with pytest.raises(
             OSError, match="Failed to inspect possible Markdown import path"
         ) as exc_info:
             memory.import_data("memory.md", format="markdown")
 
-    assert isinstance(exc_info.value.__cause__, PermissionError)
-    assert "inspection denied" in str(exc_info.value.__cause__)
+    assert exc_info.value.errno == errno.EACCES
+    assert exc_info.value.filename == "blocked-memory.md"
+    assert "inspection denied" in str(exc_info.value)
+    assert exc_info.value.__cause__ is original_error
 
 
 def test_legacy_dict_import_behavior_is_unchanged():