diff --git a/Lib/test/test_types.py b/Lib/test/test_types.py
index 7e9b28236..4200cb8ee 100644
--- a/Lib/test/test_types.py
+++ b/Lib/test/test_types.py
@@ -838,8 +838,6 @@ class UnionTests(unittest.TestCase):
         self.assertEqual((list[T] | list[S])[int, T], list[int] | list[T])
         self.assertEqual((list[T] | list[S])[int, int], list[int])
 
-    # TODO: RUSTPYTHON
-    @unittest.expectedFailure
     def test_union_parameter_substitution(self):
         def eq(actual, expected, typed=True):
             self.assertEqual(actual, expected)
diff --git a/crates/vm/src/builtins/type.rs b/crates/vm/src/builtins/type.rs
index 4f150d925..bc567cd09 100644
--- a/crates/vm/src/builtins/type.rs
+++ b/crates/vm/src/builtins/type.rs
@@ -1963,7 +1963,7 @@ pub(crate) fn call_slot_new(
     slot_new(subtype, args, vm)
 }
 
-pub(super) fn or_(zelf: PyObjectRef, other: PyObjectRef, vm: &VirtualMachine) -> PyObjectRef {
+pub(crate) fn or_(zelf: PyObjectRef, other: PyObjectRef, vm: &VirtualMachine) -> PyObjectRef {
     if !union_::is_unionable(zelf.clone(), vm) || !union_::is_unionable(other.clone(), vm) {
         return vm.ctx.not_implemented();
     }
diff --git a/crates/vm/src/builtins/union.rs b/crates/vm/src/builtins/union.rs
index 8310201a1..83e1316d0 100644
--- a/crates/vm/src/builtins/union.rs
+++ b/crates/vm/src/builtins/union.rs
@@ -8,6 +8,7 @@ use crate::{
     convert::{ToPyObject, ToPyResult},
     function::PyComparisonValue,
     protocol::{PyMappingMethods, PyNumberMethods},
+    stdlib::typing::TypeAliasType,
     types::{AsMapping, AsNumber, Comparable, GetAttr, Hashable, PyComparisonOp, Representable},
 };
 use std::fmt;
@@ -152,10 +153,12 @@ impl PyUnion {
 }
 
 pub fn is_unionable(obj: PyObjectRef, vm: &VirtualMachine) -> bool {
-    obj.class().is(vm.ctx.types.none_type)
+    let cls = obj.class();
+    cls.is(vm.ctx.types.none_type)
         || obj.downcastable::<PyType>()
-        || obj.class().is(vm.ctx.types.generic_alias_type)
-        || obj.class().is(vm.ctx.types.union_type)
+        || cls.fast_issubclass(vm.ctx.types.generic_alias_type)
+        || cls.is(vm.ctx.types.union_type)
+        || obj.downcast_ref::<TypeAliasType>().is_some()
 }
 
 fn make_parameters(args: &Py<PyTuple>, vm: &VirtualMachine) -> PyTupleRef {
@@ -195,7 +198,7 @@ fn dedup_and_flatten_args(args: &Py<PyTuple>, vm: &VirtualMachine) -> PyTupleRef
         if !new_args.iter().any(|param| {
             param
                 .rich_compare_bool(arg, PyComparisonOp::Eq, vm)
-                .expect("types are always comparable")
+                .unwrap_or_default()
         }) {
             new_args.push(arg.clone());
         }
diff --git a/crates/vm/src/stdlib/typing.rs b/crates/vm/src/stdlib/typing.rs
index 469a75b01..f11acce34 100644
--- a/crates/vm/src/stdlib/typing.rs
+++ b/crates/vm/src/stdlib/typing.rs
@@ -36,9 +36,11 @@ pub(crate) fn make_module(vm: &VirtualMachine) -> PyRef<PyModule> {
 pub(crate) mod decl {
     use crate::{
         Py, PyObjectRef, PyPayload, PyResult, VirtualMachine,
-        builtins::{PyStrRef, PyTupleRef, PyType, PyTypeRef, pystr::AsPyStr},
+        builtins::{PyStrRef, PyTupleRef, PyType, PyTypeRef, pystr::AsPyStr, type_},
+        convert::ToPyResult,
         function::{FuncArgs, IntoFuncArgs},
-        types::{Constructor, Representable},
+        protocol::PyNumberMethods,
+        types::{AsNumber, Constructor, Representable},
     };
 
     pub(crate) fn _call_typing_func_object<'a>(
@@ -109,7 +111,7 @@ pub(crate) mod decl {
         // compute_value: PyObjectRef,
         // module: PyObjectRef,
     }
-    #[pyclass(with(Constructor, Representable), flags(BASETYPE))]
+    #[pyclass(with(Constructor, Representable, AsNumber), flags(BASETYPE))]
     impl TypeAliasType {
         pub const fn new(name: PyStrRef, type_params: PyTupleRef, value: PyObjectRef) -> Self {
             Self {
@@ -183,6 +185,16 @@ pub(crate) mod decl {
         }
     }
 
+    impl AsNumber for TypeAliasType {
+        fn as_number() -> &'static PyNumberMethods {
+            static AS_NUMBER: PyNumberMethods = PyNumberMethods {
+                or: Some(|a, b, vm| type_::or_(a.to_owned(), b.to_owned(), vm).to_pyresult(vm)),
+                ..PyNumberMethods::NOT_IMPLEMENTED
+            };
+            &AS_NUMBER
+        }
+    }
+
     // impl AsMapping for Generic {
     //     fn as_mapping() -> &'static PyMappingMethods {
     //         static AS_MAPPING: Lazy<PyMappingMethods> = Lazy::new(|| PyMappingMethods {
diff --git a/extra_tests/snippets/stdlib_typing.py b/extra_tests/snippets/stdlib_typing.py
index ddc30b684..681790abd 100644
--- a/extra_tests/snippets/stdlib_typing.py
+++ b/extra_tests/snippets/stdlib_typing.py
@@ -8,3 +8,7 @@ def abort_signal_handler(
     fn: Callable[[], Awaitable[T]], on_abort: Callable[[], None] | None = None
 ) -> T:
     pass
+
+
+# Ensure PEP 604 unions work with typing.Callable aliases.
+TracebackFilter = bool | Callable[[int], int]