diff --git a/src/cleveragents/skills/inline_executor.py b/src/cleveragents/skills/inline_executor.py
index b85b69378..b10ce08d2 100644
--- a/src/cleveragents/skills/inline_executor.py
+++ b/src/cleveragents/skills/inline_executor.py
@@ -263,13 +263,15 @@ class InlineToolExecutor:
                 try:
                     resolved = Path(value).resolve()
                     sandbox_resolved = sandbox_path.resolve()
-                    if not str(resolved).startswith(str(sandbox_resolved)):
-                        return (
-                            f"Path '{value}' for key '{key}' escapes sandbox "
-                            f"root '{sandbox_path}'"
-                        )
-                except (OSError, ValueError):
-                    return f"Invalid path '{value}' for key '{key}'"
+                except OSError as exc:
+                    return f"Invalid path '{value}' for key '{key}': {exc}"
+                try:
+                    resolved.relative_to(sandbox_resolved)
+                except ValueError:
+                    return (
+                        f"Path '{value}' for key '{key}' escapes sandbox "
+                        f"root '{sandbox_path}'"
+                    )
         return None
 
     def _run_with_timeout(