diff --git a/Lib/test/test_type_annotations.py b/Lib/test/test_type_annotations.py
index c98b99e98e9..2b95cabf2e4 100644
--- a/Lib/test/test_type_annotations.py
+++ b/Lib/test/test_type_annotations.py
@@ -1,5 +1,6 @@
 import annotationlib
 import inspect
+import itertools
 import textwrap
 import types
 import unittest
@@ -782,6 +783,21 @@ def test_non_name_annotations(self):
 
 
 class RegressionTests(unittest.TestCase):
+    # gh-154902
+    def test_conditional_annotations_rebound(self):
+        # user code can rebind __conditional_annotations__ to any object
+        lefts = ("__conditional_annotations__",
+                 'globals()["__conditional_annotations__"]')
+        values = ("0", "{}", "[]", "''", "object()", "frozenset()")
+        for left, value in itertools.product(lefts, values):
+            with self.subTest(left=left, value=value):
+                code = f"""
+                    {left} = {value}
+                    x: int
+                """
+                with self.assertRaises(TypeError):
+                    run_code(code)
+
     # gh-132479
     def test_complex_comprehension_inlining(self):
         # Test that the various repro cases from the issue don't crash
diff --git a/crates/vm/src/frame.rs b/crates/vm/src/frame.rs
index cc54ad6ee18..6080e4d851b 100644
--- a/crates/vm/src/frame.rs
+++ b/crates/vm/src/frame.rs
@@ -5587,10 +5587,10 @@ impl ExecutingFrame<'_> {
             Instruction::SetAdd { i } => {
                 let item = self.pop_value();
                 let obj = self.nth_value(i.get(arg) - 1);
-                let set: &Py<PySet> = unsafe {
-                    // SAFETY: trust compiler
-                    obj.downcast_unchecked_ref()
-                };
+                // Annotation tracking can load a user-rebound global here.
+                let set = obj.downcast_ref_if_exact::<PySet>(vm).ok_or_else(|| {
+                    vm.new_type_error(format!("'{}' object is not a set", obj.class().name()))
+                })?;
                 set.add(item, vm)?;
                 Ok(None)
             }
diff --git a/crates/vm/src/vm/mod.rs b/crates/vm/src/vm/mod.rs
index 7cc636b37e3..4a74479f43d 100644
--- a/crates/vm/src/vm/mod.rs
+++ b/crates/vm/src/vm/mod.rs
@@ -1514,9 +1514,7 @@ impl VirtualMachine {
 
                 // No stdio: set to None (embedding use case)
                 #[cfg(not(feature = "stdio"))]
-                let make_stdio = |_name: &str, _fd: i32, _write: bool| {
-                    Ok(crate::builtins::PyNone.into_pyobject(self))
-                };
+                let make_stdio = |_name: &str, _fd: i32, _write: bool| Ok(self.ctx.none());
 
                 let set_stdio = |name, fd, write| {
                     let stdio: PyObjectRef = make_stdio(name, fd, write)?;
@@ -3925,6 +3923,26 @@ pub fn resolve_frozen_alias(name: &str) -> &str {
 mod tests {
     use super::*;
 
+    #[cfg(not(feature = "stdio"))]
+    #[test]
+    fn no_stdio_streams_are_none_singleton() {
+        Interpreter::builder(Default::default())
+            .build()
+            .enter(|vm| {
+                for name in [
+                    "stdin",
+                    "stdout",
+                    "stderr",
+                    "__stdin__",
+                    "__stdout__",
+                    "__stderr__",
+                ] {
+                    let stream = vm.sys_module.get_attr(name, vm).unwrap();
+                    assert!(vm.is_none(&stream), "sys.{name} must be the None singleton");
+                }
+            });
+    }
+
     #[test]
     fn nested_frozen() {
         use rustpython_vm as vm;