diff --git a/tests/test_dummy.py b/_archive/retired-tests/test_dummy.py
similarity index 100%
rename from tests/test_dummy.py
rename to _archive/retired-tests/test_dummy.py
diff --git a/src/api_contract_guardian/cli.py b/src/api_contract_guardian/cli.py
index 248e4a2..390dc95 100644
--- a/src/api_contract_guardian/cli.py
+++ b/src/api_contract_guardian/cli.py
@@ -65,6 +65,23 @@ def _validate_output_format(
     return format_name
 
 
+def _stderr_console() -> Any:
+    """A Rich console bound to stderr (errors must never pollute stdout,
+    which CI pipes consume for --format json/yaml output)."""
+    from rich.console import Console
+
+    return Console(stderr=True)
+
+
+def _write_output(output: str, content: str) -> None:
+    """Write CLI --output content, creating missing parent directories
+    instead of crashing with an unhandled FileNotFoundError traceback."""
+    out_path = Path(output)
+    if out_path.parent and not out_path.parent.exists():
+        out_path.parent.mkdir(parents=True, exist_ok=True)
+    out_path.write_text(content, encoding="utf-8")
+
+
 app = typer.Typer(
     name="api-contract-guardian",
     help="Detect breaking changes in OpenAPI specs and gate CI pipelines.",
@@ -111,9 +128,7 @@ def _load_and_validate(path: str) -> dict:
         validate_openapi_version(spec)
         return spec
     except SpecLoadError as e:
-        from rich.console import Console
-
-        Console().print(f"[red]Error loading: {e}[/red]")
+        _stderr_console().print(f"[red]Error loading: {e}[/red]")
         raise typer.Exit(code=1) from e
 
 
@@ -194,7 +209,7 @@ def diff(
     if format == "json":
         output_data = json.dumps(result.to_dict(), indent=2)
         if output:
-            Path(output).write_text(output_data, encoding="utf-8")
+            _write_output(output, output_data)
             console.print(f"Written to {output}")
         else:
             console.print(output_data)
@@ -203,14 +218,14 @@ def diff(
             result.to_dict(), sort_keys=False, default_flow_style=False
         )
         if output:
-            Path(output).write_text(output_data, encoding="utf-8")
+            _write_output(output, output_data)
             console.print(f"Written to {output}")
         else:
             console.print(output_data)
     elif format == "markdown":
         guide = generate_migration_guide(result)
         if output:
-            Path(output).write_text(guide, encoding="utf-8")
+            _write_output(output, guide)
             console.print(f"Written to {output}")
         else:
             console.print(guide)
@@ -218,7 +233,7 @@ def diff(
         _print_result(result)
         if output:
             output_data = json.dumps(result.to_dict(), indent=2)
-            Path(output).write_text(output_data, encoding="utf-8")
+            _write_output(output, output_data)
             console.print(f"\nJSON output written to {output}")
 
 
@@ -302,7 +317,7 @@ def check(
             )
         else:
             output_data = json.dumps(payload, indent=2)
-        Path(output).write_text(output_data, encoding="utf-8")
+        _write_output(output, output_data)
         console.print(f"\nWritten to {output}")
 
     raise typer.Exit(code=gate_result.exit_code)
@@ -343,7 +358,7 @@ def migrate(
         content = generate_migration_guide(result)
 
     if output:
-        Path(output).write_text(content, encoding="utf-8")
+        _write_output(output, content)
         console.print(f"Migration guide written to {output}")
     else:
         console.print(content)
diff --git a/tests/test_cli.py b/tests/test_cli.py
index ec6f322..dd41202 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -128,3 +128,22 @@ def test_migrate_valid_specs(self, tmp_path) -> None:
         assert out.exists()
         text = out.read_text(encoding="utf-8")
         assert "Migration Guide" in text
+
+
+class TestErrorObservability:
+    """Errors go to stderr and --output creates missing parent dirs."""
+
+    def test_load_error_goes_to_stderr(self) -> None:
+        result = _run("diff", "does-not-exist.yaml", "also-missing.yaml")
+        assert result.returncode == 1
+        assert "Error loading" in result.stderr
+        assert "Error" not in result.stdout
+
+    def test_diff_output_creates_parent_dirs(self, tmp_path: Path) -> None:
+        out = tmp_path / "nested" / "dir" / "report.json"
+        result = _run(
+            "diff", str(SPEC_V1), str(SPEC_V2), "--format", "json", "--output", str(out)
+        )
+        assert result.returncode == 0
+        assert out.exists()
+        assert "Written to" in result.stdout