diff --git a/src/app_model/expressions/_expressions.py b/src/app_model/expressions/_expressions.py
index e765ec9a..7035ad12 100644
--- a/src/app_model/expressions/_expressions.py
+++ b/src/app_model/expressions/_expressions.py
@@ -153,9 +153,6 @@ class Expr(ast.AST, Generic[T]):
     >>> new_expr.eval(dict(v2="hello!", myvar=8))
     'hello!'
 
-    you can also use keyword arguments.  This is *slightly* slower
-    >>> new_expr.eval(v2="hello!", myvar=4)
-
     serialize
     >>> str(new_expr)
     'myvar > 5 and v2'
@@ -184,6 +181,7 @@ def __init__(self, *args: Any, **kwargs: Any) -> None:
         if type(self).__name__ == "Expr":
             raise RuntimeError("Don't instantiate Expr. Use `Expr.parse`")
         super().__init__(*args, **kwargs)
+        self.eval = self.eval_with_callables  # type: ignore[method-assign]
         self._recompile()
 
     def _recompile(self) -> None:
@@ -191,21 +189,51 @@ def _recompile(self) -> None:
         self._code = compile(ast.Expression(body=self), "<Expr>", "eval")
         self._names = set(self._iter_names())
 
-    def eval(
-        self, context: Mapping[str, object] | None = None, **ctx_kwargs: object
-    ) -> T:
+    def eval(self, context: Mapping[str, object] | None = None) -> T:
+        """Evaluate this expression with names in `context`.
+
+        Parameters
+        ----------
+        context : Mapping[str, object] | None
+            Mapping of names to objects to evaluate the expression with.
+        """
+        # will have been replaced in __init__
+        raise NotImplementedError("This method should have been replaced.")
+
+    def eval_no_callables(self, context: Mapping[str, object] | None = None) -> T:
         """Evaluate this expression with names in `context`."""
         if context is None:
-            context = ctx_kwargs
-        elif ctx_kwargs:
-            context = {**context, **ctx_kwargs}
+            context = {}
         try:
-            return eval(self._code, {}, context)  # type: ignore
+            return eval(self._code, {}, context)  # type: ignore[no-any-return]
         except NameError as e:
-            miss = {k for k in self._names if k not in context}
-            raise NameError(
-                f"Names required to eval this expression are missing: {miss}"
-            ) from e
+            raise self._missing_names_error(context) from e
+
+    def eval_with_callables(self, context: Mapping[str, object] | None = None) -> T:
+        """Evaluate this expression with names in `context`, allowing callables."""
+        if context is None:
+            return self.eval_no_callables({})
+
+        # build a new context, evaluating any callables
+        # we only want to evaluate the callables if they are needed, so we
+        # build a new context with only the names in this expression.
+        ctx = {}
+        for name in self._names:
+            if name in context:
+                ctx[name] = val() if callable(val := context[name]) else val
+            else:
+                # early exit if we're missing names
+                raise self._missing_names_error(context)
+        return self.eval_no_callables(ctx)
+
+    def _missing_names_error(self, context: Mapping[str, object]) -> NameError:
+        """More informative error message when names are missing."""
+        miss = {k for k in self._names if k not in context}
+        num_keys = len(context)
+        return NameError(
+            f"Names required to eval expression '{self}' are missing: {miss}. "
+            f"Context has {num_keys} keys."
+        )
 
     @classmethod
     def parse(cls, expr: str) -> Expr:
diff --git a/tests/test_context/test_expressions.py b/tests/test_context/test_expressions.py
index a62d69fb..71d536df 100644
--- a/tests/test_context/test_expressions.py
+++ b/tests/test_context/test_expressions.py
@@ -236,12 +236,6 @@ def test_safe_eval():
         safe_eval("{1,2,3}")
 
 
-def test_eval_kwargs():
-    expr = parse_expression("a + b")
-    assert expr.eval(a=1, b=2) == 3
-    assert expr.eval({"a": 2}, b=2) == 4
-
-
 @pytest.mark.parametrize("expr", GOOD_EXPRESSIONS)
 def test_hash(expr):
     assert isinstance(hash(parse_expression(expr)), int)
diff --git a/tests/test_qt/test_qmenu.py b/tests/test_qt/test_qmenu.py
index cc28d34c..b6865c23 100644
--- a/tests/test_qt/test_qmenu.py
+++ b/tests/test_qt/test_qmenu.py
@@ -61,7 +61,9 @@ def test_menu(
     assert redo_action.isEnabled()
 
     # useful error when we forget a required name
-    with pytest.raises(NameError, match="Names required to eval this expression"):
+    with pytest.raises(
+        NameError, match="Names required to eval expression 'allow_undo_redo'"
+    ):
         menu.update_from_context({})
 
     menu._disconnect()