diff --git a/ouroboros/tools/registry.py b/ouroboros/tools/registry.py
index 17822a11..dc3e9399 100644
--- a/ouroboros/tools/registry.py
+++ b/ouroboros/tools/registry.py
@@ -964,8 +964,7 @@ class ToolRegistry:
                                 resolved = pathlib.Path(candidate).resolve(strict=False)
                             except Exception:
                                 continue
-                            if any(resolved.is_relative_to(allowed_root) for allowed_root in allowed_data_roots):
-                                continue
+                            if any(resolved.is_relative_to(allowed_root) for allowed_root in allowed_data_roots): continue
                             for protected_path in protected_paths:
                                 try:
                                     resolved.relative_to(protected_path)
@@ -979,6 +978,7 @@ class ToolRegistry:
                                 if not pro_workspace_passthrough:
                                     return "⚠️ WORKSPACE_SHELL_BLOCKED: write-like shell commands may not target absolute paths outside the active workspace."
                             continue
+                        if any(path_text_is_inside(candidate, root) for root in allowed_data_roots): continue
                         for protected_path in protected_paths:
                             if path_text_is_inside(candidate, protected_path):
                                 return "⚠️ WORKSPACE_SHELL_BLOCKED: write-like shell command mentions Ouroboros system/data paths."
diff --git a/tests/test_headless_cli.py b/tests/test_headless_cli.py
index 6354e1c8..7b671844 100644
--- a/tests/test_headless_cli.py
+++ b/tests/test_headless_cli.py
@@ -769,7 +769,7 @@ def test_workspace_shell_keeps_symlinked_workspace_absolute_paths_allowed(tmp_pa
     registry.set_context(ctx)
 
     target = workspace_link / "inside.txt"
-    result = registry.execute("run_command", {"cmd": f"touch {target}"})
+    result = registry.execute("run_command", {"cmd": [sys.executable, "-c", f"open({str(target)!r}, 'w').write('ok')"]})
 
     assert "WORKSPACE_SHELL_BLOCKED" not in result, result
     assert (real_workspace / "inside.txt").exists()