diff --git a/Lib/test/test_str.py b/Lib/test/test_str.py
index 15cee0d3a..56fccea7d 100644
--- a/Lib/test/test_str.py
+++ b/Lib/test/test_str.py
@@ -2414,7 +2414,6 @@ class StrTest(string_tests.StringLikeTest,
         else:
             self.fail("Should have raised UnicodeDecodeError")
 
-    @unittest.expectedFailure  # TODO: RUSTPYTHON; AssertionError: <class 'str'> is not <class 'test.test_str.StrSubclass'>
     def test_conversion(self):
         # Make sure __str__() works properly
         class StrWithStr(str):
diff --git a/crates/vm/src/builtins/str.rs b/crates/vm/src/builtins/str.rs
index b94893fe9..40c9905c1 100644
--- a/crates/vm/src/builtins/str.rs
+++ b/crates/vm/src/builtins/str.rs
@@ -406,6 +406,18 @@ impl Constructor for PyStr {
         }
 
         let args: Self::Args = func_args.bind(vm)?;
+
+        // CPython parity: when cls is exactly str, return the __str__ / __repr__
+        // result as-is so any str subclass type the user returned is preserved
+        // (matches unicode_new_impl which only invokes unicode_subtype_new when
+        // type != &PyUnicode_Type).
+        if cls.is(vm.ctx.types.str_type)
+            && args.encoding.is_missing()
+            && let OptionalArg::Present(input) = &args.object
+        {
+            return Ok(input.str(vm)?.into());
+        }
+
         let payload = Self::py_new(&cls, args, vm)?;
         payload.into_ref_with_type(vm, cls).map(Into::into)
     }