diff --git a/Lib/test/test_weakref.py b/Lib/test/test_weakref.py
index 74f937014..5b5b50eff 100644
--- a/Lib/test/test_weakref.py
+++ b/Lib/test/test_weakref.py
@@ -403,7 +403,6 @@ class ReferencesTestCase(TestBase):
         p2 = makeref(o)
         self.assertIs(p1, p2, "callbacks were None, NULL in the C API")
 
-    @unittest.expectedFailure  # TODO: RUSTPYTHON
     def test_callable_proxy(self):
         o = Callable()
         ref1 = weakref.proxy(o)
diff --git a/crates/vm/src/builtins/mod.rs b/crates/vm/src/builtins/mod.rs
index f08a2b467..cb5ee93c7 100644
--- a/crates/vm/src/builtins/mod.rs
+++ b/crates/vm/src/builtins/mod.rs
@@ -90,7 +90,7 @@ pub use traceback::PyTraceback;
 pub(crate) mod tuple;
 pub use tuple::{PyTuple, PyTupleRef};
 pub(crate) mod weakproxy;
-pub use weakproxy::PyWeakProxy;
+pub use weakproxy::{PyWeakCallableProxy, PyWeakProxy};
 pub(crate) mod weakref;
 pub use weakref::PyWeak;
 pub(crate) mod zip;
diff --git a/crates/vm/src/builtins/weakproxy.rs b/crates/vm/src/builtins/weakproxy.rs
index 35871c07b..7f39044b4 100644
--- a/crates/vm/src/builtins/weakproxy.rs
+++ b/crates/vm/src/builtins/weakproxy.rs
@@ -8,8 +8,8 @@ use crate::{
     protocol::{PyIter, PyIterReturn, PyMappingMethods, PyNumberMethods, PySequenceMethods},
     stdlib::builtins::reversed,
     types::{
-        AsMapping, AsNumber, AsSequence, Comparable, Constructor, GetAttr, Hashable, IterNext,
-        Iterable, PyComparisonOp, Representable, SetAttr,
+        AsMapping, AsNumber, AsSequence, Callable, Comparable, Constructor, GetAttr, Hashable,
+        IterNext, Iterable, PyComparisonOp, Representable, SetAttr,
     },
 };
 
@@ -67,7 +67,11 @@ impl PyWeakProxy {
         callback: Option<PyObjectRef>,
         vm: &VirtualMachine,
     ) -> PyResult<PyRef<PyWeak>> {
-        let typ = vm.ctx.types.weakproxy_type.to_owned();
+        let typ = if referent.is_callable() {
+            vm.ctx.types.weakcallableproxy_type.to_owned()
+        } else {
+            vm.ctx.types.weakproxy_type.to_owned()
+        };
         referent.downgrade_with_typ(callback, typ, vm)
     }
 
@@ -77,6 +81,28 @@ impl PyWeakProxy {
     }
 }
 
+#[pyclass(
+    module = false,
+    name = "weakcallableproxy",
+    base = PyWeakProxy,
+    ctx = "weakcallableproxy_type",
+    unhashable = true
+)]
+#[derive(Debug)]
+#[repr(transparent)]
+pub struct PyWeakCallableProxy(PyWeakProxy);
+
+#[pyclass(with(Callable))]
+impl PyWeakCallableProxy {}
+
+impl Callable for PyWeakCallableProxy {
+    type Args = FuncArgs;
+
+    fn call(zelf: &Py<Self>, args: FuncArgs, vm: &VirtualMachine) -> PyResult {
+        zelf.0.try_upgrade(vm)?.call(args, vm)
+    }
+}
+
 #[pyclass(with(
     GetAttr,
     SetAttr,
@@ -371,6 +397,7 @@ impl Representable for PyWeakProxy {
 
 pub(crate) fn init(context: &'static Context) {
     PyWeakProxy::extend_class(context, context.types.weakproxy_type);
+    PyWeakCallableProxy::extend_class(context, context.types.weakcallableproxy_type);
 }
 
 impl Hashable for PyWeakProxy {
diff --git a/crates/vm/src/object/core.rs b/crates/vm/src/object/core.rs
index b0ebfb186..be9eef29b 100644
--- a/crates/vm/src/object/core.rs
+++ b/crates/vm/src/object/core.rs
@@ -771,10 +771,12 @@ impl WeakRefList {
             Some(candidate) => {
                 let node = unsafe { candidate.as_ref() };
                 let has_callback = unsafe { (&*node.0.payload.callback.get()).is_some() };
+                let node_cls = node.class();
                 // PyWeakref_CheckProxy: the basic-proxy slot is reserved for
                 // the canonical proxy type; subclasses and callback-less ref
                 // subclasses must not be mistaken for it.
-                let is_proxy = node.class().is(crate::builtins::PyWeakProxy::static_type());
+                let is_proxy = node_cls.is(crate::builtins::PyWeakProxy::static_type())
+                    || node_cls.is(crate::builtins::PyWeakCallableProxy::static_type());
                 if has_callback || !is_proxy {
                     ptr::null_mut()
                 } else {
@@ -1602,7 +1604,8 @@ impl PyObject {
             None
         };
         let cls_is_weakref = typ.is(vm.ctx.types.weakref_type);
-        let cls_is_weakproxy = typ.is(vm.ctx.types.weakproxy_type);
+        let cls_is_weakproxy =
+            typ.is(vm.ctx.types.weakproxy_type) || typ.is(vm.ctx.types.weakcallableproxy_type);
         let wrl = self.weak_ref_list().ok_or_else(|| {
             vm.new_type_error(format!(
                 "cannot create weak reference to '{}' object",
diff --git a/crates/vm/src/stdlib/_weakref.rs b/crates/vm/src/stdlib/_weakref.rs
index 4db8970ba..ee8f1153b 100644
--- a/crates/vm/src/stdlib/_weakref.rs
+++ b/crates/vm/src/stdlib/_weakref.rs
@@ -35,7 +35,7 @@ mod _weakref {
 
     #[pyattr(name = "CallableProxyType")]
     fn callable_proxy_type(vm: &VirtualMachine) -> PyTypeRef {
-        vm.ctx.types.weakproxy_type.to_owned()
+        vm.ctx.types.weakcallableproxy_type.to_owned()
     }
 
     #[pyfunction]
diff --git a/crates/vm/src/types/zoo.rs b/crates/vm/src/types/zoo.rs
index c8667050b..49afa928a 100644
--- a/crates/vm/src/types/zoo.rs
+++ b/crates/vm/src/types/zoo.rs
@@ -86,6 +86,7 @@ pub struct TypeZoo {
     pub bound_method_type: &'static Py<PyType>,
     pub weakref_type: &'static Py<PyType>,
     pub weakproxy_type: &'static Py<PyType>,
+    pub weakcallableproxy_type: &'static Py<PyType>,
     pub mappingproxy_type: &'static Py<PyType>,
     pub traceback_type: &'static Py<PyType>,
     pub object_type: &'static Py<PyType>,
@@ -198,6 +199,7 @@ impl TypeZoo {
             traceback_type: traceback::PyTraceback::init_builtin_type(),
             tuple_iterator_type: tuple::PyTupleIterator::init_builtin_type(),
             weakproxy_type: weakproxy::PyWeakProxy::init_builtin_type(),
+            weakcallableproxy_type: weakproxy::PyWeakCallableProxy::init_builtin_type(),
             method_descriptor_type: descriptor::PyMethodDescriptor::init_builtin_type(),
             none_type: singletons::PyNone::init_builtin_type(),
             typing_no_default_type: crate::stdlib::_typing::NoDefault::init_builtin_type(),