diff --git a/src/cleveragents/skills/inline_executor.py b/src/cleveragents/skills/inline_executor.py
index b85b69378..f6aaf7666 100644
--- a/src/cleveragents/skills/inline_executor.py
+++ b/src/cleveragents/skills/inline_executor.py
@@ -263,7 +263,8 @@ class InlineToolExecutor:
                 try:
                     resolved = Path(value).resolve()
                     sandbox_resolved = sandbox_path.resolve()
-                    if not str(resolved).startswith(str(sandbox_resolved)):
+                    rel = os.path.relpath(str(resolved), str(sandbox_resolved))
+                    if rel.startswith(".."):
                         return (
                             f"Path '{value}' for key '{key}' escapes sandbox "
                             f"root '{sandbox_path}'"