diff --git a/Lib/test/test_os.py b/Lib/test/test_os.py
index d968aa87f..30a24e28d 100644
--- a/Lib/test/test_os.py
+++ b/Lib/test/test_os.py
@@ -1811,7 +1811,6 @@ class MakedirTests(unittest.TestCase):
         # Issue #25583: A drive root could raise PermissionError on Windows
         os.makedirs(os.path.abspath('/'), exist_ok=True)
 
-    @unittest.expectedFailureIfWindows('TODO: RUSTPYTHON; os.umask not implemented yet for all platforms')
     @unittest.skipIf(
         support.is_emscripten or support.is_wasi,
         "Emscripten's/WASI's umask is a stub."
@@ -4653,7 +4652,6 @@ class FDInheritanceTests(unittest.TestCase):
         os.set_inheritable(fd, False)
         self.assertEqual(os.get_inheritable(fd), False)
 
-    @unittest.expectedFailureIfWindows('TODO: RUSTPYTHON; os.get_inheritable not implemented yet for all platforms')
     def test_get_set_inheritable_badf(self):
         fd = os_helper.make_bad_fd()
 
diff --git a/crates/vm/src/function/fspath.rs b/crates/vm/src/function/fspath.rs
index 5e0108986..2bc331844 100644
--- a/crates/vm/src/function/fspath.rs
+++ b/crates/vm/src/function/fspath.rs
@@ -14,8 +14,26 @@ pub enum FsPath {
 }
 
 impl FsPath {
+    pub fn try_from_path_like(
+        obj: PyObjectRef,
+        check_for_nul: bool,
+        vm: &VirtualMachine,
+    ) -> PyResult<Self> {
+        Self::try_from(
+            obj,
+            check_for_nul,
+            "expected str, bytes or os.PathLike object",
+            vm,
+        )
+    }
+
     // PyOS_FSPath in CPython
-    pub fn try_from(obj: PyObjectRef, check_for_nul: bool, vm: &VirtualMachine) -> PyResult<Self> {
+    pub fn try_from(
+        obj: PyObjectRef,
+        check_for_nul: bool,
+        msg: &'static str,
+        vm: &VirtualMachine,
+    ) -> PyResult<Self> {
         let check_nul = |b: &[u8]| {
             if !check_for_nul || memchr::memchr(b'\0', b).is_none() {
                 Ok(())
@@ -41,13 +59,16 @@ impl FsPath {
             Ok(pathlike) => return Ok(pathlike),
             Err(obj) => obj,
         };
-        let method =
-            vm.get_method_or_type_error(obj.clone(), identifier!(vm, __fspath__), || {
-                format!(
-                    "should be string, bytes, os.PathLike or integer, not {}",
-                    obj.class().name()
-                )
-            })?;
+        let not_pathlike_error = || format!("{msg}, not {}", obj.class().name());
+        let method = vm.get_method_or_type_error(
+            obj.clone(),
+            identifier!(vm, __fspath__),
+            not_pathlike_error,
+        )?;
+        // If __fspath__ is explicitly set to None, treat it as if it doesn't have __fspath__
+        if vm.is_none(&method) {
+            return Err(vm.new_type_error(not_pathlike_error()));
+        }
         let result = method.call((), vm)?;
         match1(result)?.map_err(|result| {
             vm.new_type_error(format!(
@@ -125,6 +146,6 @@ impl TryFromObject for FsPath {
             }
             Err(_) => obj,
         };
-        Self::try_from(obj, true, vm)
+        Self::try_from_path_like(obj, true, vm)
     }
 }
diff --git a/crates/vm/src/ospath.rs b/crates/vm/src/ospath.rs
index 5083c1df5..add40f9b2 100644
--- a/crates/vm/src/ospath.rs
+++ b/crates/vm/src/ospath.rs
@@ -55,6 +55,14 @@ impl OsPath {
         Ok(Self { path, mode })
     }
 
+    /// Convert an object to OsPath using the os.fspath-style error message.
+    /// This is used by open() which should report "expected str, bytes or os.PathLike object, not"
+    /// instead of "should be string, bytes or os.PathLike, not".
+    pub(crate) fn try_from_fspath(obj: PyObjectRef, vm: &VirtualMachine) -> PyResult<Self> {
+        let fspath = FsPath::try_from_path_like(obj, true, vm)?;
+        Self::from_fspath(fspath, vm)
+    }
+
     pub fn as_path(&self) -> &Path {
         Path::new(&self.path)
     }
@@ -90,7 +98,12 @@ impl AsRef<Path> for OsPath {
 impl TryFromObject for OsPath {
     // TODO: path_converter with allow_fd=0 in CPython
     fn try_from_object(vm: &VirtualMachine, obj: PyObjectRef) -> PyResult<Self> {
-        let fspath = FsPath::try_from(obj, true, vm)?;
+        let fspath = FsPath::try_from(
+            obj,
+            true,
+            "should be string, bytes, os.PathLike or integer",
+            vm,
+        )?;
         Self::from_fspath(fspath, vm)
     }
 }
diff --git a/crates/vm/src/stdlib/io.rs b/crates/vm/src/stdlib/io.rs
index 39ea310c9..8efd52a29 100644
--- a/crates/vm/src/stdlib/io.rs
+++ b/crates/vm/src/stdlib/io.rs
@@ -4340,7 +4340,7 @@ mod fileio {
                     }
                     (fd, None)
                 } else {
-                    let path = OsPath::try_from_object(vm, name.clone())?;
+                    let path = OsPath::try_from_fspath(name.clone(), vm)?;
                     #[cfg(any(unix, target_os = "wasi"))]
                     let fd = crt_fd::open(&path.clone().into_cstring(vm)?, flags, 0o666);
                     #[cfg(windows)]
diff --git a/crates/vm/src/stdlib/os.rs b/crates/vm/src/stdlib/os.rs
index 378cffd83..0034b087a 100644
--- a/crates/vm/src/stdlib/os.rs
+++ b/crates/vm/src/stdlib/os.rs
@@ -1022,7 +1022,7 @@ pub(super) mod _os {
 
     #[pyfunction]
     fn fspath(path: PyObjectRef, vm: &VirtualMachine) -> PyResult<FsPath> {
-        FsPath::try_from(path, false, vm)
+        FsPath::try_from_path_like(path, false, vm)
     }
 
     #[pyfunction]