diff --git a/native/Cargo.lock b/native/Cargo.lock
index 4ca4809c..0ba138ea 100644
--- a/native/Cargo.lock
+++ b/native/Cargo.lock
@@ -355,9 +355,9 @@ dependencies = [
 
 [[package]]
 name = "once_cell"
-version = "1.16.0"
+version = "1.21.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "86f0b0d4bf799edbc74508c1e8bf170ff5f41238e5f8225603ca7caaae2b7860"
+checksum = "42f5e15c9953c5e4ccceeb2e7382a716482c34515315f7b03532b8b4e8393d2d"
 
 [[package]]
 name = "oorandom"
@@ -443,9 +443,9 @@ dependencies = [
 
 [[package]]
 name = "pyo3"
-version = "0.25.1"
+version = "0.26.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8970a78afe0628a3e3430376fc5fd76b6b45c4d43360ffd6cdd40bdde72b682a"
+checksum = "7ba0117f4212101ee6544044dae45abe1083d30ce7b29c4b5cbdfa2354e07383"
 dependencies = [
  "indoc",
  "libc",
@@ -460,19 +460,18 @@ dependencies = [
 
 [[package]]
 name = "pyo3-build-config"
-version = "0.25.1"
+version = "0.26.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "458eb0c55e7ece017adeba38f2248ff3ac615e53660d7c71a238d7d2a01c7598"
+checksum = "4fc6ddaf24947d12a9aa31ac65431fb1b851b8f4365426e182901eabfb87df5f"
 dependencies = [
- "once_cell",
  "target-lexicon",
 ]
 
 [[package]]
 name = "pyo3-ffi"
-version = "0.25.1"
+version = "0.26.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7114fe5457c61b276ab77c5055f206295b812608083644a5c5b2640c3102565c"
+checksum = "025474d3928738efb38ac36d4744a74a400c901c7596199e20e45d98eb194105"
 dependencies = [
  "libc",
  "pyo3-build-config",
@@ -480,9 +479,9 @@ dependencies = [
 
 [[package]]
 name = "pyo3-macros"
-version = "0.25.1"
+version = "0.26.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a8725c0a622b374d6cb051d11a0983786448f7785336139c3c94f5aa6bef7e50"
+checksum = "2e64eb489f22fe1c95911b77c44cc41e7c19f3082fc81cce90f657cdc42ffded"
 dependencies = [
  "proc-macro2",
  "pyo3-macros-backend",
@@ -492,9 +491,9 @@ dependencies = [
 
 [[package]]
 name = "pyo3-macros-backend"
-version = "0.25.1"
+version = "0.26.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4109984c22491085343c05b0dbc54ddc405c3cf7b4374fc533f5c3313a572ccc"
+checksum = "100246c0ecf400b475341b8455a9213344569af29a3c841d29270e53102e0fcf"
 dependencies = [
  "heck",
  "proc-macro2",
diff --git a/native/libcst/Cargo.toml b/native/libcst/Cargo.toml
index d65a60cc..4fb029ca 100644
--- a/native/libcst/Cargo.toml
+++ b/native/libcst/Cargo.toml
@@ -36,7 +36,7 @@ trace = ["peg/trace"]
 
 [dependencies]
 paste = "1.0.15"
-pyo3 = { version = "0.25.1", optional = true }
+pyo3 = { version = "0.26", optional = true }
 thiserror = "2.0.12"
 peg = "0.8.5"
 annotate-snippets = "0.11.5"
diff --git a/native/libcst/src/nodes/expression.rs b/native/libcst/src/nodes/expression.rs
index 961eee9f..c72d301d 100644
--- a/native/libcst/src/nodes/expression.rs
+++ b/native/libcst/src/nodes/expression.rs
@@ -2670,8 +2670,8 @@ mod py {
     use crate::nodes::traits::py::TryIntoPy;
 
     // TODO: this could be a derive helper attribute to override the python class name
-    impl<'a> TryIntoPy<pyo3::PyObject> for Element<'a> {
-        fn try_into_py(self, py: pyo3::Python) -> pyo3::PyResult<pyo3::PyObject> {
+    impl<'a> TryIntoPy<pyo3::Py<pyo3::PyAny>> for Element<'a> {
+        fn try_into_py(self, py: pyo3::Python) -> pyo3::PyResult<pyo3::Py<pyo3::PyAny>> {
             match self {
                 Self::Starred(s) => s.try_into_py(py),
                 Self::Simple { value, comma } => {
@@ -2699,8 +2699,8 @@ mod py {
     }
 
     // TODO: this could be a derive helper attribute to override the python class name
-    impl<'a> TryIntoPy<pyo3::PyObject> for DictElement<'a> {
-        fn try_into_py(self, py: pyo3::Python) -> pyo3::PyResult<pyo3::PyObject> {
+    impl<'a> TryIntoPy<pyo3::Py<pyo3::PyAny>> for DictElement<'a> {
+        fn try_into_py(self, py: pyo3::Python) -> pyo3::PyResult<pyo3::Py<pyo3::PyAny>> {
             match self {
                 Self::Starred(s) => s.try_into_py(py),
                 Self::Simple {
diff --git a/native/libcst/src/nodes/macros.rs b/native/libcst/src/nodes/macros.rs
index c9ed49c1..11028b8c 100644
--- a/native/libcst/src/nodes/macros.rs
+++ b/native/libcst/src/nodes/macros.rs
@@ -17,8 +17,8 @@ macro_rules! py_import {
     ( $module_name:expr, $member_name:expr, $getter_fn:ident ) => {
         paste::paste! {
             static [<IMPORT_CELL_ $getter_fn:snake:upper>]
-                : pyo3::once_cell::GILOnceCell<pyo3::PyResult<pyo3::PyObject>>
-                = pyo3::once_cell::GILOnceCell::new();
+                : pyo3::once_cell::PyOnceLock<pyo3::PyResult<pyo3::Py<pyo3::PyAny>>>
+                = pyo3::once_cell::PyOnceLock::new();
 
             fn $getter_fn<'py>(py: pyo3::Python<'py>) -> pyo3::PyResult<&'py pyo3::PyAny> {
                 Ok([<IMPORT_CELL_ $getter_fn:snake:upper>].get_or_init(py, || {
diff --git a/native/libcst/src/nodes/parser_config.rs b/native/libcst/src/nodes/parser_config.rs
index c10d86d5..e274d8df 100644
--- a/native/libcst/src/nodes/parser_config.rs
+++ b/native/libcst/src/nodes/parser_config.rs
@@ -29,12 +29,12 @@ impl BaseWhitespaceParserConfig {
     }
 
     #[getter]
-    fn get_lines(&self, py: Python) -> PyObject {
+    fn get_lines(&self, py: Python) -> Py<PyAny> {
         self.lines.to_object(py)
     }
 
     #[getter]
-    fn get_default_newline(&self, py: Python) -> PyObject {
+    fn get_default_newline(&self, py: Python) -> Py<PyAny> {
         self.default_newline.to_object(py)
     }
 }
@@ -62,23 +62,23 @@ impl BaseWhitespaceParserConfig {
     }
 }
 
-// These fields are private and PyObject, since we don't currently care about using them from
+// These fields are private and Py<PyAny>, since we don't currently care about using them from
 // within rust.
 #[pyclass(extends=BaseWhitespaceParserConfig, module="libcst_native.parser_config")]
 #[text_signature = "(*, lines, encoding, default_indent, default_newline, has_trailing_newline, version, future_imports)"]
 pub struct ParserConfig {
     // lines is inherited
     #[pyo3(get)]
-    encoding: PyObject,
+    encoding: Py<PyAny>,
     #[pyo3(get)]
-    default_indent: PyObject,
+    default_indent: Py<PyAny>,
     // default_newline is inherited
     #[pyo3(get)]
-    has_trailing_newline: PyObject,
+    has_trailing_newline: Py<PyAny>,
     #[pyo3(get)]
-    version: PyObject,
+    version: Py<PyAny>,
     #[pyo3(get)]
-    future_imports: PyObject,
+    future_imports: Py<PyAny>,
 }
 
 #[pymethods]
@@ -86,12 +86,12 @@ impl ParserConfig {
     #[new]
     fn new(
         lines: &PySequence,
-        encoding: PyObject,
-        default_indent: PyObject,
+        encoding: Py<PyAny>,
+        default_indent: Py<PyAny>,
         default_newline: &PyString,
-        has_trailing_newline: PyObject,
-        version: PyObject,
-        future_imports: PyObject,
+        has_trailing_newline: Py<PyAny>,
+        version: Py<PyAny>,
+        future_imports: Py<PyAny>,
     ) -> PyResult<(Self, BaseWhitespaceParserConfig)> {
         Ok((
             Self {
diff --git a/native/libcst/src/nodes/py_cached.rs b/native/libcst/src/nodes/py_cached.rs
index d2398051..307082da 100644
--- a/native/libcst/src/nodes/py_cached.rs
+++ b/native/libcst/src/nodes/py_cached.rs
@@ -7,11 +7,11 @@ use pyo3::prelude::*;
 use std::convert::AsRef;
 use std::ops::Deref;
 
-/// An immutable wrapper around a rust type T and it's PyObject equivalent. Caches the conversion
-/// to and from the PyObject.
+/// An immutable wrapper around a rust type T and its Py<PyAny> equivalent. Caches the conversion
+/// to and from the Py<PyAny>.
 pub struct PyCached<T> {
     native: T,
-    py_object: PyObject,
+    py_object: Py<PyAny>,
 }
 
 impl<T> PyCached<T>
@@ -31,7 +31,7 @@ where
     T: FromPyObject<'source>,
 {
     fn extract(ob: &'source PyAny) -> PyResult<Self> {
-        Python::with_gil(|py| {
+        Python::attach(|py| {
             Ok(PyCached {
                 native: ob.extract()?,
                 py_object: ob.to_object(py),
@@ -40,14 +40,14 @@ where
     }
 }
 
-impl<T> IntoPy<PyObject> for PyCached<T> {
-    fn into_py(self, _py: Python) -> PyObject {
+impl<T> IntoPy<Py<PyAny>> for PyCached<T> {
+    fn into_py(self, _py: Python) -> Py<PyAny> {
         self.py_object
     }
 }
 
 impl<T> ToPyObject for PyCached<T> {
-    fn to_object(&self, py: Python) -> PyObject {
+    fn to_object(&self, py: Python) -> Py<PyAny> {
         self.py_object.clone_ref(py)
     }
 }
@@ -71,6 +71,6 @@ where
     T: ToPyObject,
 {
     fn from(val: T) -> Self {
-        Python::with_gil(|py| Self::new(py, val))
+        Python::attach(|py| Self::new(py, val))
     }
 }
diff --git a/native/libcst/src/nodes/traits.rs b/native/libcst/src/nodes/traits.rs
index df61538b..c15a60e1 100644
--- a/native/libcst/src/nodes/traits.rs
+++ b/native/libcst/src/nodes/traits.rs
@@ -118,7 +118,7 @@ impl<'a, T: Inflate<'a>> Inflate<'a> for Vec<T> {
 }
 #[cfg(feature = "py")]
 pub mod py {
-    use pyo3::{types::PyTuple, IntoPyObjectExt, PyObject, PyResult, Python};
+    use pyo3::{types::PyTuple, IntoPyObjectExt, Py, PyAny, PyResult, Python};
 
     // TODO: replace with upstream implementation once
     // https://github.com/PyO3/pyo3/issues/1813 is resolved
@@ -133,26 +133,26 @@ pub mod py {
     //     }
     // }
 
-    impl TryIntoPy<PyObject> for bool {
-        fn try_into_py(self, py: Python) -> PyResult<PyObject> {
+    impl TryIntoPy<Py<PyAny>> for bool {
+        fn try_into_py(self, py: Python) -> PyResult<Py<PyAny>> {
             self.into_py_any(py)
         }
     }
 
-    impl<T: TryIntoPy<PyObject>> TryIntoPy<PyObject> for Box<T>
+    impl<T: TryIntoPy<Py<PyAny>>> TryIntoPy<Py<PyAny>> for Box<T>
     where
-        T: TryIntoPy<PyObject>,
+        T: TryIntoPy<Py<PyAny>>,
     {
-        fn try_into_py(self, py: Python) -> PyResult<PyObject> {
+        fn try_into_py(self, py: Python) -> PyResult<Py<PyAny>> {
             (*self).try_into_py(py)
         }
     }
 
-    impl<T> TryIntoPy<PyObject> for Option<T>
+    impl<T> TryIntoPy<Py<PyAny>> for Option<T>
     where
-        T: TryIntoPy<PyObject>,
+        T: TryIntoPy<Py<PyAny>>,
     {
-        fn try_into_py(self, py: Python) -> PyResult<PyObject> {
+        fn try_into_py(self, py: Python) -> PyResult<Py<PyAny>> {
             Ok(match self {
                 None => py.None(),
                 Some(x) => x.try_into_py(py)?,
@@ -160,11 +160,11 @@ pub mod py {
         }
     }
 
-    impl<T> TryIntoPy<PyObject> for Vec<T>
+    impl<T> TryIntoPy<Py<PyAny>> for Vec<T>
     where
-        T: TryIntoPy<PyObject>,
+        T: TryIntoPy<Py<PyAny>>,
     {
-        fn try_into_py(self, py: Python) -> PyResult<PyObject> {
+        fn try_into_py(self, py: Python) -> PyResult<Py<PyAny>> {
             let converted = self
                 .into_iter()
                 .map(|x| x.try_into_py(py))
@@ -174,8 +174,8 @@ pub mod py {
         }
     }
 
-    impl<'a> TryIntoPy<PyObject> for &'a str {
-        fn try_into_py(self, py: Python) -> PyResult<PyObject> {
+    impl<'a> TryIntoPy<Py<PyAny>> for &'a str {
+        fn try_into_py(self, py: Python) -> PyResult<Py<PyAny>> {
             self.into_py_any(py)
         }
     }
diff --git a/native/libcst/src/parser/errors.rs b/native/libcst/src/parser/errors.rs
index 8237cd0b..7fb3b740 100644
--- a/native/libcst/src/parser/errors.rs
+++ b/native/libcst/src/parser/errors.rs
@@ -35,7 +35,7 @@ mod py_error {
 
     impl<'a> From<ParserError<'a>> for PyErr {
         fn from(e: ParserError) -> Self {
-            Python::with_gil(|py| {
+            Python::attach(|py| {
                 let lines = match &e {
                     ParserError::TokenizerError(_, text) | ParserError::ParserError(_, text) => {
                         text.lines().collect::<Vec<_>>()
diff --git a/native/libcst/src/py.rs b/native/libcst/src/py.rs
index 57da11e7..68c03744 100644
--- a/native/libcst/src/py.rs
+++ b/native/libcst/src/py.rs
@@ -11,21 +11,21 @@ use pyo3::prelude::*;
 pub fn libcst_native(_py: Python, m: &Bound<PyModule>) -> PyResult<()> {
     #[pyfn(m)]
     #[pyo3(signature = (source, encoding=None))]
-    fn parse_module(source: String, encoding: Option<&str>) -> PyResult<PyObject> {
+    fn parse_module(source: String, encoding: Option<&str>) -> PyResult<Py<PyAny>> {
         let m = crate::parse_module(source.as_str(), encoding)?;
-        Python::with_gil(|py| m.try_into_py(py))
+        Python::attach(|py| m.try_into_py(py))
     }
 
     #[pyfn(m)]
-    fn parse_expression(source: String) -> PyResult<PyObject> {
+    fn parse_expression(source: String) -> PyResult<Py<PyAny>> {
         let expr = crate::parse_expression(source.as_str())?;
-        Python::with_gil(|py| expr.try_into_py(py))
+        Python::attach(|py| expr.try_into_py(py))
     }
 
     #[pyfn(m)]
-    fn parse_statement(source: String) -> PyResult<PyObject> {
+    fn parse_statement(source: String) -> PyResult<Py<PyAny>> {
         let stm = crate::parse_statement(source.as_str())?;
-        Python::with_gil(|py| stm.try_into_py(py))
+        Python::attach(|py| stm.try_into_py(py))
     }
 
     Ok(())