diff --git a/src/app_model/backends/qt/_qaction.py b/src/app_model/backends/qt/_qaction.py
index 748e77f..49cb5bc 100644
--- a/src/app_model/backends/qt/_qaction.py
+++ b/src/app_model/backends/qt/_qaction.py
@@ -44,7 +44,10 @@ def __init__(
         self.triggered.connect(self._on_triggered)
 
     def _on_triggered(self, checked: bool) -> None:
-        self._app.commands.execute_command(self._command_id)
+        # execute_command returns a Future, for the sake of eventually being
+        # asynchronous without breaking the API.  For now, we call result()
+        # to raise any exceptions.
+        self._app.commands.execute_command(self._command_id).result()
 
 
 class QCommandRuleAction(QCommandAction):
@@ -80,10 +83,13 @@ def __init__(
             self.setToolTip(command_rule.tooltip)
         if command_rule.status_tip:
             self.setStatusTip(command_rule.status_tip)
+        self.setCheckable(command_rule.toggled is not None)
 
     def update_from_context(self, ctx: Mapping[str, object]) -> None:
         """Update the enabled state of this menu item from `ctx`."""
         self.setEnabled(expr.eval(ctx) if (expr := self._cmd_rule.enablement) else True)
+        if expr := self._cmd_rule.toggled:
+            self.setChecked(expr.eval(ctx))
 
 
 class QMenuItemAction(QCommandRuleAction):
diff --git a/src/app_model/types/_command_rule.py b/src/app_model/types/_command_rule.py
index 2b7aa42..dabf556 100644
--- a/src/app_model/types/_command_rule.py
+++ b/src/app_model/types/_command_rule.py
@@ -52,6 +52,11 @@ class CommandRule(_StrictModel):
         "the UI. Menus pick either `title` or `short_title` depending on the context "
         "in which they show commands.",
     )
+    toggled: Optional[expressions.Expr] = Field(
+        None,
+        description="(Optional) Condition under which the command should appear "
+        "in any GUI representation (like a menu).",
+    )
 
     def _as_command_rule(self) -> "CommandRule":
         """Simplify (subclasses) to a plain CommandRule."""
diff --git a/tests/conftest.py b/tests/conftest.py
index a814580..ed15e21 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -32,6 +32,7 @@ class Commands:
     REDO = "redo"
     COPY = "copy"
     PASTE = "paste"
+    TOGGLE_THING = "toggle_thing"
     OPEN_FROM_A = "open.from_a"
     OPEN_FROM_B = "open.from_b"
     UNIMPORTABLE = "unimportable"
@@ -195,6 +196,13 @@ def build_app(name: str = "complete_test_app") -> FullApp:
             title="Will raise an error",
             callback=_raise_an_error,
         ),
+        Action(
+            id=Commands.TOGGLE_THING,
+            title="Toggle Thing",
+            callback=lambda: None,
+            menus=[{"id": Menus.HELP}],
+            toggled="thing_toggled",
+        ),
     ]
     for action in actions:
         app.register_action(action)
diff --git a/tests/test_qt/test_qmenu.py b/tests/test_qt/test_qmenu.py
index d41a72a..b3996a2 100644
--- a/tests/test_qt/test_qmenu.py
+++ b/tests/test_qt/test_qmenu.py
@@ -127,3 +127,16 @@ def test_cache_action(full_app: "FullApp") -> None:
     a1 = QMenuItemAction(action, full_app)
     a2 = QMenuItemAction(action, full_app)
     assert a1 is a2
+
+
+def test_toggled_menu_item(qtbot: "QtBot", full_app: "FullApp") -> None:
+    app = full_app
+    menu = QModelMenu(app.Menus.HELP, app)
+    qtbot.addWidget(menu)
+
+    menu.update_from_context({"thing_toggled": True})
+    action = menu.findAction(app.Commands.TOGGLE_THING)
+    assert action.isChecked()
+
+    menu.update_from_context({"thing_toggled": False})
+    assert not action.isChecked()