diff --git a/Lib/test/test_bool.py b/Lib/test/test_bool.py
index 09eefd422..34ecb45f1 100644
--- a/Lib/test/test_bool.py
+++ b/Lib/test/test_bool.py
@@ -46,8 +46,6 @@ class BoolTest(unittest.TestCase):
         self.assertEqual(complex(True), 1+0j)
         self.assertEqual(complex(True), True)
 
-    # TODO: RUSTPYTHON
-    @unittest.expectedFailure
     def test_math(self):
         self.assertEqual(+False, 0)
         self.assertIsNot(+False, False)
diff --git a/vm/src/vm/vm_ops.rs b/vm/src/vm/vm_ops.rs
index 09f849a1a..5235393a6 100644
--- a/vm/src/vm/vm_ops.rs
+++ b/vm/src/vm/vm_ops.rs
@@ -1,4 +1,5 @@
 use super::VirtualMachine;
+use crate::stdlib::warnings;
 use crate::{
     builtins::{PyInt, PyIntRef, PyStr, PyStrRef},
     object::{AsObject, PyObject, PyObjectRef, PyResult},
@@ -469,6 +470,17 @@ impl VirtualMachine {
     }
 
     pub fn _invert(&self, a: &PyObject) -> PyResult {
+        const STR: &str = "Bitwise inversion '~' on bool is deprecated and will be removed in Python 3.16. \
+            This returns the bitwise inversion of the underlying int object and is usually not what you expect from negating a bool. \
+            Use the 'not' operator for boolean negation or ~int(x) if you really want the bitwise inversion of the underlying int.";
+        if a.fast_isinstance(self.ctx.types.bool_type) {
+            warnings::warn(
+                self.ctx.exceptions.deprecation_warning,
+                STR.to_owned(),
+                1,
+                self,
+            )?;
+        }
         self.get_special_method(a, identifier!(self, __invert__))?
             .ok_or_else(|| self.new_unsupported_unary_error(a, "unary ~"))?
             .invoke((), self)