diff --git a/fill_resistance/config.py b/fill_resistance/config.py
index 43c8b07..8976f1b 100644
--- a/fill_resistance/config.py
+++ b/fill_resistance/config.py
@@ -2,6 +2,9 @@
 
 A future version may read overrides from <project>/fill_res_config.json.
 """
+from __future__ import annotations   # KiCad's macOS Python is 3.9: without
+                                     # this, `float | None` annotations are
+                                     # evaluated at import and crash there
 
 # --- Grid sizing ---
 # Benchmarked on the VOUT+ plane (147x59 mm): R changes < 0.3% from
diff --git a/tests/test_py39_compat.py b/tests/test_py39_compat.py
new file mode 100644
index 0000000..eb9cd47
--- /dev/null
+++ b/tests/test_py39_compat.py
@@ -0,0 +1,51 @@
+"""Python 3.9 compatibility tripwire.
+
+KiCad's macOS builds bundle Python 3.9 and build the plugin venv with
+it (README: Platform notes), while the dev environment runs a current
+Python - so nothing else in the suite notices a construct that only
+breaks on 3.9. The first real Mac run died at import: a module-level
+`float | None` annotation in config.py, evaluated at runtime because
+the file lacked the future import (PEP 604 unions need Python 3.10
+unless annotations are deferred).
+"""
+import ast
+from pathlib import Path
+
+ROOT = Path(__file__).resolve().parent.parent
+SHIPPED = sorted((ROOT / "fill_resistance").glob("*.py"))
+SHIPPED.append(ROOT / "fill_res_action.py")
+
+
+def _has_future_annotations(tree: ast.Module) -> bool:
+    return any(isinstance(node, ast.ImportFrom)
+               and node.module == "__future__"
+               and any(alias.name == "annotations" for alias in node.names)
+               for node in tree.body)
+
+
+def _uses_annotations(tree: ast.Module) -> bool:
+    for node in ast.walk(tree):
+        if isinstance(node, ast.AnnAssign):
+            return True
+        if isinstance(node, (ast.FunctionDef, ast.AsyncFunctionDef)):
+            if node.returns is not None:
+                return True
+            a = node.args
+            args = (a.posonlyargs + a.args + a.kwonlyargs
+                    + ([a.vararg] if a.vararg else [])
+                    + ([a.kwarg] if a.kwarg else []))
+            if any(arg.annotation is not None for arg in args):
+                return True
+    return False
+
+
+def test_annotated_modules_defer_annotations():
+    offenders = []
+    for path in SHIPPED:
+        tree = ast.parse(path.read_text(encoding="utf-8"), filename=str(path))
+        if _uses_annotations(tree) and not _has_future_annotations(tree):
+            offenders.append(path.name)
+    assert not offenders, (
+        f"{offenders} use annotations without 'from __future__ import "
+        f"annotations': they are evaluated at import time and PEP 604 "
+        f"unions crash on KiCad's macOS Python 3.9.")