diff --git a/crates/vm/src/vm/mod.rs b/crates/vm/src/vm/mod.rs
index a26ab3761..28e59a2f4 100644
--- a/crates/vm/src/vm/mod.rs
+++ b/crates/vm/src/vm/mod.rs
@@ -23,8 +23,8 @@ mod vm_ops;
 use crate::{
     AsObject, Py, PyObject, PyObjectRef, PyPayload, PyRef, PyResult,
     builtins::{
-        self, PyBaseExceptionRef, PyDict, PyDictRef, PyInt, PyList, PyModule, PyStr, PyStrInterned,
-        PyStrRef, PyTypeRef, PyUtf8Str, PyUtf8StrInterned, PyWeak,
+        self, PyBaseExceptionRef, PyBaseObject, PyDict, PyDictRef, PyInt, PyList, PyModule, PyStr,
+        PyStrInterned, PyStrRef, PyTypeRef, PyUtf8Str, PyUtf8StrInterned, PyWeak,
         code::PyCode,
         dict::{PyDictItems, PyDictKeys, PyDictValues},
         pystr::AsPyStr,
@@ -42,6 +42,7 @@ use crate::{
     scope::Scope,
     signal::{self, SignalHandlers},
     stdlib,
+    types::{GetattroFunc, fn_addr},
     warn::WarningsState,
 };
 use alloc::{borrow::Cow, collections::BTreeMap};
@@ -2854,8 +2855,14 @@ impl VirtualMachine {
         attr_name: impl AsPyStr<'a>,
     ) -> PyResult<Option<PyObjectRef>> {
         let attr_name = attr_name.as_pystr(&self.ctx);
-        match obj.get_attr_inner(attr_name, self) {
-            Ok(attr) => Ok(Some(attr)),
+        let getattro = obj.class().slots.getattro.load().unwrap();
+        let result = if fn_addr(getattro) == fn_addr(PyBaseObject::getattro as GetattroFunc) {
+            obj.generic_getattr_opt(attr_name, None, self)
+        } else {
+            obj.get_attr_inner(attr_name, self).map(Some)
+        };
+        match result {
+            Ok(attr) => Ok(attr),
             Err(e) if e.fast_isinstance(self.ctx.exceptions.attribute_error) => Ok(None),
             Err(e) => Err(e),
         }
diff --git a/extra_tests/snippets/builtin_optional_attr.py b/extra_tests/snippets/builtin_optional_attr.py
new file mode 100644
index 000000000..3e501b3cd
--- /dev/null
+++ b/extra_tests/snippets/builtin_optional_attr.py
@@ -0,0 +1,126 @@
+def assert_raises(exc_type, func, *args):
+    try:
+        func(*args)
+    except exc_type:
+        return
+    except BaseException as exc:
+        raise AssertionError(
+            f"expected {exc_type.__name__}, got {type(exc).__name__}"
+        ) from exc
+    raise AssertionError(f"expected {exc_type.__name__}")
+
+
+class Plain:
+    class_attr = "class"
+
+
+plain = Plain()
+plain.instance_attr = "instance"
+sentinel = object()
+
+assert hasattr(plain, "class_attr")
+assert hasattr(plain, "instance_attr")
+assert not hasattr(plain, "missing")
+assert getattr(plain, "class_attr", sentinel) == "class"
+assert getattr(plain, "instance_attr", sentinel) == "instance"
+assert getattr(plain, "missing", sentinel) is sentinel
+assert_raises(AttributeError, getattr, plain, "missing")
+assert_raises(TypeError, hasattr, plain, 1)
+assert_raises(TypeError, getattr, plain, 1, sentinel)
+
+
+getattribute_calls = []
+
+
+class CustomGetattribute:
+    def __getattribute__(self, name):
+        getattribute_calls.append(name)
+        if name == "missing":
+            raise AttributeError("custom miss")
+        if name == "bad":
+            raise ValueError("custom error")
+        return f"value:{name}"
+
+
+custom_getattribute = CustomGetattribute()
+assert not hasattr(custom_getattribute, "missing")
+assert getattr(custom_getattribute, "missing", sentinel) is sentinel
+assert getattribute_calls == ["missing", "missing"]
+assert getattr(custom_getattribute, "present", sentinel) == "value:present"
+assert_raises(ValueError, hasattr, custom_getattribute, "bad")
+
+
+getattr_calls = []
+
+
+class CustomGetattr:
+    def __getattr__(self, name):
+        getattr_calls.append(name)
+        if name == "present":
+            return "fallback value"
+        if name == "bad":
+            raise SystemExit("custom error")
+        raise AttributeError(name)
+
+
+custom_getattr = CustomGetattr()
+assert getattr(custom_getattr, "present", sentinel) == "fallback value"
+assert not hasattr(custom_getattr, "missing")
+assert getattr_calls == ["present", "missing"]
+assert_raises(SystemExit, hasattr, custom_getattr, "bad")
+
+
+class AttributeErrorSubclass(AttributeError):
+    pass
+
+
+class AttributeErrorDescriptor:
+    def __get__(self, obj, owner):
+        raise AttributeError("descriptor miss")
+
+
+class AttributeErrorSubclassDescriptor:
+    def __get__(self, obj, owner):
+        raise AttributeErrorSubclass("descriptor miss")
+
+
+class ValueErrorDescriptor:
+    def __get__(self, obj, owner):
+        raise ValueError("descriptor error")
+
+
+class DescriptorContainer:
+    attribute_error = AttributeErrorDescriptor()
+    attribute_error_subclass = AttributeErrorSubclassDescriptor()
+    value_error = ValueErrorDescriptor()
+
+
+descriptor_container = DescriptorContainer()
+assert not hasattr(descriptor_container, "attribute_error")
+assert getattr(descriptor_container, "attribute_error", sentinel) is sentinel
+assert not hasattr(descriptor_container, "attribute_error_subclass")
+assert getattr(descriptor_container, "attribute_error_subclass", sentinel) is sentinel
+assert_raises(ValueError, hasattr, descriptor_container, "value_error")
+
+
+class Dynamic:
+    pass
+
+
+dynamic = Dynamic()
+assert not hasattr(dynamic, "missing")
+dynamic_calls = []
+
+
+def dynamic_getattribute(self, name):
+    dynamic_calls.append(name)
+    if name == "missing":
+        raise AttributeError(name)
+    return object.__getattribute__(self, name)
+
+
+Dynamic.__getattribute__ = dynamic_getattribute
+assert not hasattr(dynamic, "missing")
+del Dynamic.__getattribute__
+assert not hasattr(dynamic, "missing")
+assert dynamic_calls == ["missing"]