diff --git a/.github/CONTRIBUTING.md b/.github/CONTRIBUTING.md
index ad79743953f..f5a08e2d787 100644
--- a/.github/CONTRIBUTING.md
+++ b/.github/CONTRIBUTING.md
@@ -135,7 +135,7 @@ The valid options are:
 * Use `-G` and the name of a generator to use something different. `cmake
   --help` lists the generators available.
       - On Unix, setting `CMAKE_GENERATER=Ninja` in your environment will give
-        you automatic mulithreading on all your CMake projects!
+        you automatic multithreading on all your CMake projects!
 * Open the `CMakeLists.txt` with QtCreator to generate for that IDE.
 * You can use `-DCMAKE_EXPORT_COMPILE_COMMANDS=ON` to generate the `.json` file
   that some tools expect.
diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index f4f392c8c73..f9be10badad 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -32,13 +32,13 @@ repos:
 
 # Black, the code formatter, natively supports pre-commit
 - repo: https://github.com/psf/black-pre-commit-mirror
-  rev: "23.7.0" # Keep in sync with blacken-docs
+  rev: "23.9.1" # Keep in sync with blacken-docs
   hooks:
   - id: black
 
 # Ruff, the Python auto-correcting linter written in Rust
 - repo: https://github.com/astral-sh/ruff-pre-commit
-  rev: v0.0.287
+  rev: v0.0.292
   hooks:
   - id: ruff
     args: ["--fix", "--show-fixes"]
@@ -126,7 +126,7 @@ repos:
 # Use tools/codespell_ignore_lines_from_errors.py
 # to rebuild .codespell-ignore-lines
 - repo: https://github.com/codespell-project/codespell
-  rev: "v2.2.5"
+  rev: "v2.2.6"
   hooks:
   - id: codespell
     exclude: ".supp$"
@@ -134,7 +134,7 @@ repos:
 
 # Check for common shell mistakes
 - repo: https://github.com/shellcheck-py/shellcheck-py
-  rev: "v0.9.0.5"
+  rev: "v0.9.0.6"
   hooks:
   - id: shellcheck
 
@@ -144,12 +144,12 @@ repos:
   - id: disallow-caps
     name: Disallow improper capitalization
     language: pygrep
-    entry: PyBind|Numpy|Cmake|CCache|PyTest
+    entry: PyBind|\bNumpy\b|Cmake|CCache|PyTest
     exclude: ^\.pre-commit-config.yaml$
 
 # PyLint has native support - not always usable, but works for us
 - repo: https://github.com/PyCQA/pylint
-  rev: "v3.0.0a7"
+  rev: "v3.0.0"
   hooks:
   - id: pylint
     files: ^pybind11
diff --git a/CMakeLists.txt b/CMakeLists.txt
index 7b349508cc6..6321d6b144f 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -5,6 +5,11 @@
 # All rights reserved. Use of this source code is governed by a
 # BSD-style license that can be found in the LICENSE file.
 
+# Propagate this policy (FindPythonInterp removal) so it can be detected later
+if(NOT CMAKE_VERSION VERSION_LESS "3.27")
+  cmake_policy(GET CMP0148 _pybind11_cmp0148)
+endif()
+
 cmake_minimum_required(VERSION 3.5)
 
 # The `cmake_minimum_required(VERSION 3.5...3.26)` syntax does not work with
@@ -16,6 +21,11 @@ else()
   cmake_policy(VERSION 3.26)
 endif()
 
+if(_pybind11_cmp0148)
+  cmake_policy(SET CMP0148 ${_pybind11_cmp0148})
+  unset(_pybind11_cmp0148)
+endif()
+
 # Avoid infinite recursion if tests include this as a subdirectory
 if(DEFINED PYBIND11_MASTER_PROJECT)
   return()
diff --git a/include/pybind11/cast.h b/include/pybind11/cast.h
index f6ab98e49e5..bfc2680225c 100644
--- a/include/pybind11/cast.h
+++ b/include/pybind11/cast.h
@@ -817,7 +817,7 @@ class tuple_caster {
     }
 
     static constexpr auto name
-        = const_name("Tuple[") + concat(make_caster<Ts>::name...) + const_name("]");
+        = const_name("tuple[") + concat(make_caster<Ts>::name...) + const_name("]");
 
     template <typename T>
     using cast_op_type = type;
@@ -1044,6 +1044,10 @@ struct handle_type_name<bytes> {
     static constexpr auto name = const_name(PYBIND11_BYTES_NAME);
 };
 template <>
+struct handle_type_name<buffer> {
+    static constexpr auto name = const_name("Buffer");
+};
+template <>
 struct handle_type_name<int_> {
     static constexpr auto name = const_name("int");
 };
@@ -1064,10 +1068,18 @@ struct handle_type_name<function> {
     static constexpr auto name = const_name("Callable");
 };
 template <>
+struct handle_type_name<handle> {
+    static constexpr auto name = handle_type_name<object>::name;
+};
+template <>
 struct handle_type_name<none> {
     static constexpr auto name = const_name("None");
 };
 template <>
+struct handle_type_name<sequence> {
+    static constexpr auto name = const_name("Sequence");
+};
+template <>
 struct handle_type_name<args> {
     static constexpr auto name = const_name("*args");
 };
diff --git a/include/pybind11/detail/cross_extension_shared_state.h b/include/pybind11/detail/cross_extension_shared_state.h
index 3d424cc44d4..ed36c8304ee 100644
--- a/include/pybind11/detail/cross_extension_shared_state.h
+++ b/include/pybind11/detail/cross_extension_shared_state.h
@@ -36,6 +36,7 @@ inline object get_python_state_dict() {
 #endif
     if (!state_dict) {
         raise_from(PyExc_SystemError, "pybind11::detail::get_python_state_dict() FAILED");
+        throw error_already_set();
     }
     return state_dict;
 }
@@ -95,6 +96,7 @@ struct cross_extension_shared_state {
                         " Retrieve payload_type** from capsule FAILED for ABI ID \""
                         + std::string(AdapterType::abi_id()) + "\"")
                            .c_str());
+            throw error_already_set();
         }
         payload_pp() = static_cast<payload_type **>(raw_ptr);
         return *payload_pp();
diff --git a/include/pybind11/detail/init.h b/include/pybind11/detail/init.h
index c0ad7d05c8c..0b601d6d301 100644
--- a/include/pybind11/detail/init.h
+++ b/include/pybind11/detail/init.h
@@ -69,7 +69,7 @@ constexpr bool is_alias(void *) {
 }
 
 // Constructs and returns a new object; if the given arguments don't map to a constructor, we fall
-// back to brace aggregate initiailization so that for aggregate initialization can be used with
+// back to brace aggregate initialization so that for aggregate initialization can be used with
 // py::init, e.g.  `py::init<int, int>` to initialize a `struct T { int a; int b; }`.  For
 // non-aggregate types, we need to use an ordinary T(...) constructor (invoking as `T{...}` usually
 // works, but will not do the expected thing when `T` has an `initializer_list<T>` constructor).
diff --git a/include/pybind11/detail/internals.h b/include/pybind11/detail/internals.h
index 9be2878aae8..ab2d3f1306e 100644
--- a/include/pybind11/detail/internals.h
+++ b/include/pybind11/detail/internals.h
@@ -324,6 +324,7 @@ inline internals **get_internals_pp_from_capsule(handle obj) {
     void *raw_ptr = PyCapsule_GetPointer(obj.ptr(), /*name=*/nullptr);
     if (raw_ptr == nullptr) {
         raise_from(PyExc_SystemError, "pybind11::detail::get_internals_pp_from_capsule() FAILED");
+        throw error_already_set();
     }
     return static_cast<internals **>(raw_ptr);
 }
diff --git a/include/pybind11/detail/native_enum_data.h b/include/pybind11/detail/native_enum_data.h
index 09f783f4a80..11e7f792b87 100644
--- a/include/pybind11/detail/native_enum_data.h
+++ b/include/pybind11/detail/native_enum_data.h
@@ -98,6 +98,7 @@ inline void native_enum_add_to_parent(object parent, const detail::native_enum_d
     if (!enum_module) {
         raise_from(PyExc_SystemError,
                    "`import enum` FAILED at " __FILE__ ":" PYBIND11_TOSTRING(__LINE__));
+        throw error_already_set();
     }
     auto py_enum_type = enum_module.attr(data.use_int_enum ? "IntEnum" : "Enum");
     auto py_enum = py_enum_type(data.enum_name, data.members);
diff --git a/include/pybind11/numpy.h b/include/pybind11/numpy.h
index 02f65d740dc..23c38660e9d 100644
--- a/include/pybind11/numpy.h
+++ b/include/pybind11/numpy.h
@@ -120,6 +120,20 @@ inline numpy_internals &get_numpy_internals() {
     return *ptr;
 }
 
+PYBIND11_NOINLINE module_ import_numpy_core_submodule(const char *submodule_name) {
+    module_ numpy = module_::import("numpy");
+    str version_string = numpy.attr("__version__");
+
+    module_ numpy_lib = module_::import("numpy.lib");
+    object numpy_version = numpy_lib.attr("NumpyVersion")(version_string);
+    int major_version = numpy_version.attr("major").cast<int>();
+
+    /* `numpy.core` was renamed to `numpy._core` in NumPy 2.0 as it officially
+        became a private module. */
+    std::string numpy_core_path = major_version >= 2 ? "numpy._core" : "numpy.core";
+    return module_::import((numpy_core_path + "." + submodule_name).c_str());
+}
+
 template <typename T>
 struct same_size {
     template <typename U>
@@ -263,9 +277,13 @@ struct npy_api {
     };
 
     static npy_api lookup() {
-        module_ m = module_::import("numpy.core.multiarray");
+        module_ m = detail::import_numpy_core_submodule("multiarray");
         auto c = m.attr("_ARRAY_API");
         void **api_ptr = (void **) PyCapsule_GetPointer(c.ptr(), nullptr);
+        if (api_ptr == nullptr) {
+            raise_from(PyExc_SystemError, "FAILURE obtaining numpy _ARRAY_API pointer.");
+            throw error_already_set();
+        }
         npy_api api;
 #define DECL_NPY_API(Func) api.Func##_ = (decltype(api.Func##_)) api_ptr[API_##Func];
         DECL_NPY_API(PyArray_GetNDArrayCFeatureVersion);
@@ -626,11 +644,8 @@ class dtype : public object {
 
 private:
     static object _dtype_from_pep3118() {
-        static PyObject *obj = module_::import("numpy.core._internal")
-                                   .attr("_dtype_from_pep3118")
-                                   .cast<object>()
-                                   .release()
-                                   .ptr();
+        module_ m = detail::import_numpy_core_submodule("_internal");
+        static PyObject *obj = m.attr("_dtype_from_pep3118").cast<object>().release().ptr();
         return reinterpret_borrow<object>(obj);
     }
 
diff --git a/include/pybind11/pybind11.h b/include/pybind11/pybind11.h
index 68d3d36e6da..0e2108b8116 100644
--- a/include/pybind11/pybind11.h
+++ b/include/pybind11/pybind11.h
@@ -59,11 +59,13 @@ inline std::string replace_newlines_and_squash(const char *text) {
     std::string result(text);
     bool previous_is_whitespace = false;
 
-    // Do not modify string representations
-    char first_char = result[0];
-    char last_char = result[result.size() - 1];
-    if (first_char == last_char && first_char == '\'') {
-        return result;
+    if (result.size() >= 2) {
+        // Do not modify string representations
+        char first_char = result[0];
+        char last_char = result[result.size() - 1];
+        if (first_char == last_char && first_char == '\'') {
+            return result;
+        }
     }
     result.clear();
 
@@ -1146,7 +1148,7 @@ class cpp_function : public function {
                     }
                     msg += "kwargs: ";
                     bool first = true;
-                    for (auto kwarg : kwargs) {
+                    for (const auto &kwarg : kwargs) {
                         if (first) {
                             first = false;
                         } else {
diff --git a/include/pybind11/stl.h b/include/pybind11/stl.h
index 804d9617c7f..0a5aa9cf25a 100644
--- a/include/pybind11/stl.h
+++ b/include/pybind11/stl.h
@@ -50,7 +50,7 @@ while pybind11 was very far on the strict side. Originally PyCLIF accepted any
 Python iterable as input for a C++ `vector`/`set`/`map` argument, as long as
 the elements were convertible. The obvious (in hindsight) problem was that
 any empty Python iterable could be passed to any of these C++ types, e.g. `{}`
-was accpeted for C++ `vector`/`set` arguments, or `[]` for C++ `map` arguments.
+was accepted for C++ `vector`/`set` arguments, or `[]` for C++ `map` arguments.
 
 The functions below strike a practical permissive-vs-strict compromise,
 informed by tens of thousands of use cases in the wild. A main objective is
@@ -202,7 +202,7 @@ struct set_caster {
         return s.release();
     }
 
-    PYBIND11_TYPE_CASTER_RVPP(type, const_name("Set[") + key_conv::name + const_name("]"));
+    PYBIND11_TYPE_CASTER_RVPP(type, const_name("set[") + key_conv::name + const_name("]"));
 };
 
 template <typename Type, typename Key, typename Value>
@@ -273,7 +273,7 @@ struct map_caster {
     }
 
     PYBIND11_TYPE_CASTER_RVPP(Type,
-                              const_name("Dict[") + key_conv::name + const_name(", ")
+                              const_name("dict[") + key_conv::name + const_name(", ")
                                   + value_conv::name + const_name("]"));
 };
 
@@ -340,7 +340,7 @@ struct list_caster {
         return l.release();
     }
 
-    PYBIND11_TYPE_CASTER_RVPP(Type, const_name("List[") + value_conv::name + const_name("]"));
+    PYBIND11_TYPE_CASTER_RVPP(Type, const_name("list[") + value_conv::name + const_name("]"));
 };
 
 template <typename Type, typename Alloc>
@@ -422,7 +422,7 @@ struct array_caster {
 
     PYBIND11_TYPE_CASTER_RVPP(ArrayType,
                               const_name<Resizable>(const_name(""), const_name("Annotated["))
-                                  + const_name("List[") + value_conv::name + const_name("]")
+                                  + const_name("list[") + value_conv::name + const_name("]")
                                   + const_name<Resizable>(const_name(""),
                                                           const_name(", FixedSize(")
                                                               + const_name<Size>()
diff --git a/include/pybind11/typing.h b/include/pybind11/typing.h
index 74fd82eacee..b7b1a4e54aa 100644
--- a/include/pybind11/typing.h
+++ b/include/pybind11/typing.h
@@ -45,6 +45,16 @@ class Set : public set {
     using set::set;
 };
 
+template <typename T>
+class Iterable : public iterable {
+    using iterable::iterable;
+};
+
+template <typename T>
+class Iterator : public iterator {
+    using iterator::iterator;
+};
+
 template <typename Signature>
 class Callable;
 
@@ -85,6 +95,16 @@ struct handle_type_name<typing::Set<T>> {
     static constexpr auto name = const_name("set[") + make_caster<T>::name + const_name("]");
 };
 
+template <typename T>
+struct handle_type_name<typing::Iterable<T>> {
+    static constexpr auto name = const_name("Iterable[") + make_caster<T>::name + const_name("]");
+};
+
+template <typename T>
+struct handle_type_name<typing::Iterator<T>> {
+    static constexpr auto name = const_name("Iterator[") + make_caster<T>::name + const_name("]");
+};
+
 template <typename Return, typename... Args>
 struct handle_type_name<typing::Callable<Return(Args...)>> {
     using retval_type = conditional_t<std::is_same<Return, void>::value, void_type, Return>;
diff --git a/tests/test_buffers.py b/tests/test_buffers.py
index 63d9d869fda..5d33625ba47 100644
--- a/tests/test_buffers.py
+++ b/tests/test_buffers.py
@@ -219,3 +219,10 @@ def test_ctypes_from_buffer():
         assert cinfo.shape == pyinfo.shape
         assert cinfo.strides == pyinfo.strides
         assert not cinfo.readonly
+
+
+def test_buffer_docstring():
+    assert (
+        m.get_buffer_info.__doc__.strip()
+        == "get_buffer_info(arg0: Buffer) -> pybind11_tests.buffers.buffer_info"
+    )
diff --git a/tests/test_builtin_casters.py b/tests/test_builtin_casters.py
index 61daad468ba..0fb5ef61e99 100644
--- a/tests/test_builtin_casters.py
+++ b/tests/test_builtin_casters.py
@@ -352,7 +352,7 @@ def test_tuple(doc):
     assert (
         doc(m.pair_passthrough)
         == """
-        pair_passthrough(arg0: Tuple[bool, str]) -> Tuple[str, bool]
+        pair_passthrough(arg0: tuple[bool, str]) -> tuple[str, bool]
 
         Return a pair in reversed order
     """
@@ -360,7 +360,7 @@ def test_tuple(doc):
     assert (
         doc(m.tuple_passthrough)
         == """
-        tuple_passthrough(arg0: Tuple[bool, str, int]) -> Tuple[int, str, bool]
+        tuple_passthrough(arg0: tuple[bool, str, int]) -> tuple[int, str, bool]
 
         Return a triple in reversed order
     """
diff --git a/tests/test_factory_constructors.py b/tests/test_factory_constructors.py
index f59d6cf2417..958e13e4a5f 100644
--- a/tests/test_factory_constructors.py
+++ b/tests/test_factory_constructors.py
@@ -77,7 +77,7 @@ def test_init_factory_signature(msg):
             1. m.factory_constructors.TestFactory1(arg0: m.factory_constructors.tag.unique_ptr_tag, arg1: int)
             2. m.factory_constructors.TestFactory1(arg0: str)
             3. m.factory_constructors.TestFactory1(arg0: m.factory_constructors.tag.pointer_tag)
-            4. m.factory_constructors.TestFactory1(arg0: handle, arg1: int, arg2: handle)
+            4. m.factory_constructors.TestFactory1(arg0: object, arg1: int, arg2: object)
 
         Invoked with: 'invalid', 'constructor', 'arguments'
     """
@@ -95,7 +95,7 @@ def test_init_factory_signature(msg):
 
         3. __init__(self: m.factory_constructors.TestFactory1, arg0: m.factory_constructors.tag.pointer_tag) -> None
 
-        4. __init__(self: m.factory_constructors.TestFactory1, arg0: handle, arg1: int, arg2: handle) -> None
+        4. __init__(self: m.factory_constructors.TestFactory1, arg0: object, arg1: int, arg2: object) -> None
     """
     )
 
diff --git a/tests/test_kwargs_and_defaults.cpp b/tests/test_kwargs_and_defaults.cpp
index 614c826dac3..9a12c42afa6 100644
--- a/tests/test_kwargs_and_defaults.cpp
+++ b/tests/test_kwargs_and_defaults.cpp
@@ -85,6 +85,8 @@ TEST_SUBMODULE(kwargs_and_defaults, m) {
         "kw_lb_func7",
         [](const std::string &) {},
         py::arg("str_arg") = "First line.\n  Second line.");
+    m.def(
+        "kw_lb_func8", [](const CustomRepr &) {}, py::arg("custom") = CustomRepr(""));
 
     // test_args_and_kwargs
     m.def("args_function", [](py::args args) -> py::tuple {
diff --git a/tests/test_kwargs_and_defaults.py b/tests/test_kwargs_and_defaults.py
index b577001976a..0e3bbdb7652 100644
--- a/tests/test_kwargs_and_defaults.py
+++ b/tests/test_kwargs_and_defaults.py
@@ -8,7 +8,7 @@ def test_function_signatures(doc):
     assert doc(m.kw_func1) == "kw_func1(x: int, y: int) -> str"
     assert doc(m.kw_func2) == "kw_func2(x: int = 100, y: int = 200) -> str"
     assert doc(m.kw_func3) == "kw_func3(data: str = 'Hello world!') -> None"
-    assert doc(m.kw_func4) == "kw_func4(myList: List[int] = [13, 17]) -> str"
+    assert doc(m.kw_func4) == "kw_func4(myList: list[int] = [13, 17]) -> str"
     assert doc(m.kw_func_udl) == "kw_func_udl(x: int, y: int = 300) -> str"
     assert doc(m.kw_func_udl_z) == "kw_func_udl_z(x: int, y: int = 0) -> str"
     assert doc(m.args_function) == "args_function(*args) -> tuple"
@@ -55,6 +55,10 @@ def test_function_signatures(doc):
         doc(m.kw_lb_func7)
         == "kw_lb_func7(str_arg: str = 'First line.\\n  Second line.') -> None"
     )
+    assert (
+        doc(m.kw_lb_func8)
+        == "kw_lb_func8(custom: m.kwargs_and_defaults.CustomRepr = ) -> None"
+    )
 
 
 def test_named_arguments():
diff --git a/tests/test_numpy_array.py b/tests/test_numpy_array.py
index 12e7d17d152..0697daf3efc 100644
--- a/tests/test_numpy_array.py
+++ b/tests/test_numpy_array.py
@@ -298,7 +298,7 @@ def test_constructors():
     results = m.converting_constructors([1, 2, 3])
     for a in results.values():
         np.testing.assert_array_equal(a, [1, 2, 3])
-    assert results["array"].dtype == np.int_
+    assert results["array"].dtype == np.dtype(int)
     assert results["array_t<int32>"].dtype == np.int32
     assert results["array_t<double>"].dtype == np.float64
 
diff --git a/tests/test_pytypes.cpp b/tests/test_pytypes.cpp
index b03f5624e15..0a587680f85 100644
--- a/tests/test_pytypes.cpp
+++ b/tests/test_pytypes.cpp
@@ -828,6 +828,8 @@ TEST_SUBMODULE(pytypes, m) {
     m.def("annotate_dict_str_int", [](const py::typing::Dict<py::str, int> &) {});
     m.def("annotate_list_int", [](const py::typing::List<int> &) {});
     m.def("annotate_set_str", [](const py::typing::Set<std::string> &) {});
+    m.def("annotate_iterable_str", [](const py::typing::Iterable<std::string> &) {});
+    m.def("annotate_iterator_int", [](const py::typing::Iterator<int> &) {});
     m.def("annotate_fn",
           [](const py::typing::Callable<int(py::typing::List<py::str>, py::str)> &) {});
 }
diff --git a/tests/test_pytypes.py b/tests/test_pytypes.py
index e88a9328f7a..2b2027316ca 100644
--- a/tests/test_pytypes.py
+++ b/tests/test_pytypes.py
@@ -926,6 +926,20 @@ def test_set_annotations(doc):
     assert doc(m.annotate_set_str) == "annotate_set_str(arg0: set[str]) -> None"
 
 
+def test_iterable_annotations(doc):
+    assert (
+        doc(m.annotate_iterable_str)
+        == "annotate_iterable_str(arg0: Iterable[str]) -> None"
+    )
+
+
+def test_iterator_annotations(doc):
+    assert (
+        doc(m.annotate_iterator_int)
+        == "annotate_iterator_int(arg0: Iterator[int]) -> None"
+    )
+
+
 def test_fn_annotations(doc):
     assert (
         doc(m.annotate_fn)
diff --git a/tests/test_sequences_and_iterators.py b/tests/test_sequences_and_iterators.py
index dc129f2bff4..acbe9d8983e 100644
--- a/tests/test_sequences_and_iterators.py
+++ b/tests/test_sequences_and_iterators.py
@@ -171,6 +171,10 @@ def __len__(self):
     assert m.sequence_length("hello") == 5
 
 
+def test_sequence_doc():
+    assert m.sequence_length.__doc__.strip() == "sequence_length(arg0: Sequence) -> int"
+
+
 def test_map_iterator():
     sm = m.StringMap({"hi": "bye", "black": "white"})
     assert sm["hi"] == "bye"
diff --git a/tests/test_stl.py b/tests/test_stl.py
index 2a7e916c4d0..328cc85dc31 100644
--- a/tests/test_stl.py
+++ b/tests/test_stl.py
@@ -16,8 +16,8 @@ def test_vector(doc):
     assert m.load_bool_vector([True, False])
     assert m.load_bool_vector((True, False))
 
-    assert doc(m.cast_vector) == "cast_vector() -> List[int]"
-    assert doc(m.load_vector) == "load_vector(arg0: List[int]) -> bool"
+    assert doc(m.cast_vector) == "cast_vector() -> list[int]"
+    assert doc(m.load_vector) == "load_vector(arg0: list[int]) -> bool"
 
     # Test regression caused by 936: pointers to stl containers weren't castable
     assert m.cast_ptr_vector() == ["lvalue", "lvalue"]
@@ -39,10 +39,10 @@ def test_array(doc):
     assert m.load_array(lst)
     assert m.load_array(tuple(lst))
 
-    assert doc(m.cast_array) == "cast_array() -> Annotated[List[int], FixedSize(2)]"
+    assert doc(m.cast_array) == "cast_array() -> Annotated[list[int], FixedSize(2)]"
     assert (
         doc(m.load_array)
-        == "load_array(arg0: Annotated[List[int], FixedSize(2)]) -> bool"
+        == "load_array(arg0: Annotated[list[int], FixedSize(2)]) -> bool"
     )
 
 
@@ -53,8 +53,8 @@ def test_valarray(doc):
     assert m.load_valarray(lst)
     assert m.load_valarray(tuple(lst))
 
-    assert doc(m.cast_valarray) == "cast_valarray() -> List[int]"
-    assert doc(m.load_valarray) == "load_valarray(arg0: List[int]) -> bool"
+    assert doc(m.cast_valarray) == "cast_valarray() -> list[int]"
+    assert doc(m.load_valarray) == "load_valarray(arg0: list[int]) -> bool"
 
 
 def test_map(doc):
@@ -66,8 +66,8 @@ def test_map(doc):
     assert "key2" in d
     assert m.load_map(d)
 
-    assert doc(m.cast_map) == "cast_map() -> Dict[str, str]"
-    assert doc(m.load_map) == "load_map(arg0: Dict[str, str]) -> bool"
+    assert doc(m.cast_map) == "cast_map() -> dict[str, str]"
+    assert doc(m.load_map) == "load_map(arg0: dict[str, str]) -> bool"
 
 
 def test_set(doc):
@@ -78,8 +78,8 @@ def test_set(doc):
     assert m.load_set(s)
     assert m.load_set(frozenset(s))
 
-    assert doc(m.cast_set) == "cast_set() -> Set[str]"
-    assert doc(m.load_set) == "load_set(arg0: Set[str]) -> bool"
+    assert doc(m.cast_set) == "cast_set() -> set[str]"
+    assert doc(m.load_set) == "load_set(arg0: set[str]) -> bool"
 
 
 def test_recursive_casting():
@@ -303,7 +303,7 @@ def test_stl_pass_by_pointer(msg):
         msg(excinfo.value)
         == """
         stl_pass_by_pointer(): incompatible function arguments. The following argument types are supported:
-            1. (v: List[int] = None) -> List[int]
+            1. (v: list[int] = None) -> list[int]
 
         Invoked with:
     """
@@ -315,7 +315,7 @@ def test_stl_pass_by_pointer(msg):
         msg(excinfo.value)
         == """
         stl_pass_by_pointer(): incompatible function arguments. The following argument types are supported:
-            1. (v: List[int] = None) -> List[int]
+            1. (v: list[int] = None) -> list[int]
 
         Invoked with: None
     """
diff --git a/tools/FindPythonLibsNew.cmake b/tools/FindPythonLibsNew.cmake
index ce558d4ece6..8275b9d5aaf 100644
--- a/tools/FindPythonLibsNew.cmake
+++ b/tools/FindPythonLibsNew.cmake
@@ -95,6 +95,22 @@ if(NOT PythonLibsNew_FIND_VERSION)
   set(PythonLibsNew_FIND_VERSION "3.6")
 endif()
 
+if(NOT CMAKE_VERSION VERSION_LESS "3.27")
+  cmake_policy(GET CMP0148 _pybind11_cmp0148)
+  if(NOT _pybind11_cmp0148)
+    message(
+      AUTHOR_WARNING
+        "Policy CMP0148 is not set: The FindPythonInterp and FindPythonLibs "
+        "modules are removed.  Run \"cmake --help-policy CMP0148\" for policy "
+        "details.  Use the cmake_policy command to set the policy and suppress "
+        "this warning, or preferably upgrade to using FindPython, either by "
+        "calling it explicitly before pybind11, or by setting "
+        "PYBIND11_FINDPYTHON ON before pybind11.")
+  endif()
+  cmake_policy(SET CMP0148 OLD)
+  unset(_pybind11_cmp0148)
+endif()
+
 find_package(PythonInterp ${PythonLibsNew_FIND_VERSION} ${_pythonlibs_required}
              ${_pythonlibs_quiet})
 
@@ -172,13 +188,20 @@ _pybind11_get_if_undef(_PYTHON_VALUES 0 _PYTHON_VERSION_LIST)
 _pybind11_get_if_undef(_PYTHON_VALUES 1 PYTHON_PREFIX)
 _pybind11_get_if_undef(_PYTHON_VALUES 2 PYTHON_INCLUDE_DIR)
 _pybind11_get_if_undef(_PYTHON_VALUES 3 PYTHON_SITE_PACKAGES)
-_pybind11_get_if_undef(_PYTHON_VALUES 4 PYTHON_MODULE_EXTENSION)
 _pybind11_get_if_undef(_PYTHON_VALUES 5 PYTHON_IS_DEBUG)
 _pybind11_get_if_undef(_PYTHON_VALUES 6 PYTHON_SIZEOF_VOID_P)
 _pybind11_get_if_undef(_PYTHON_VALUES 7 PYTHON_LIBRARY_SUFFIX)
 _pybind11_get_if_undef(_PYTHON_VALUES 8 PYTHON_LIBDIR)
 _pybind11_get_if_undef(_PYTHON_VALUES 9 PYTHON_MULTIARCH)
 
+list(GET _PYTHON_VALUES 4 _PYTHON_MODULE_EXT_SUFFIX)
+if(PYBIND11_PYTHONLIBS_OVERWRITE OR NOT DEFINED PYTHON_MODULE_DEBUG_POSTFIX)
+  get_filename_component(PYTHON_MODULE_DEBUG_POSTFIX "${_PYTHON_MODULE_EXT_SUFFIX}" NAME_WE)
+endif()
+if(PYBIND11_PYTHONLIBS_OVERWRITE OR NOT DEFINED PYTHON_MODULE_EXTENSION)
+  get_filename_component(PYTHON_MODULE_EXTENSION "${_PYTHON_MODULE_EXT_SUFFIX}" EXT)
+endif()
+
 # Make sure the Python has the same pointer-size as the chosen compiler
 # Skip if CMAKE_SIZEOF_VOID_P is not defined
 # This should be skipped for (non-Apple) cross-compiles (like EMSCRIPTEN)
diff --git a/tools/pybind11NewTools.cmake b/tools/pybind11NewTools.cmake
index 3a35a738631..8cee2d46091 100644
--- a/tools/pybind11NewTools.cmake
+++ b/tools/pybind11NewTools.cmake
@@ -95,25 +95,36 @@ endif()
 
 # Get the suffix - SO is deprecated, should use EXT_SUFFIX, but this is
 # required for PyPy3 (as of 7.3.1)
-if(NOT DEFINED PYTHON_MODULE_EXTENSION)
+if(NOT DEFINED PYTHON_MODULE_EXTENSION OR NOT DEFINED PYTHON_MODULE_DEBUG_POSTFIX)
   execute_process(
     COMMAND
       "${${_Python}_EXECUTABLE}" "-c"
       "import sys, importlib; s = importlib.import_module('distutils.sysconfig' if sys.version_info < (3, 10) else 'sysconfig'); print(s.get_config_var('EXT_SUFFIX') or s.get_config_var('SO'))"
-    OUTPUT_VARIABLE _PYTHON_MODULE_EXTENSION
-    ERROR_VARIABLE _PYTHON_MODULE_EXTENSION_ERR
+    OUTPUT_VARIABLE _PYTHON_MODULE_EXT_SUFFIX
+    ERROR_VARIABLE _PYTHON_MODULE_EXT_SUFFIX_ERR
     OUTPUT_STRIP_TRAILING_WHITESPACE)
 
-  if(_PYTHON_MODULE_EXTENSION STREQUAL "")
+  if(_PYTHON_MODULE_EXT_SUFFIX STREQUAL "")
     message(
       FATAL_ERROR "pybind11 could not query the module file extension, likely the 'distutils'"
-                  "package is not installed. Full error message:\n${_PYTHON_MODULE_EXTENSION_ERR}")
+                  "package is not installed. Full error message:\n${_PYTHON_MODULE_EXT_SUFFIX_ERR}"
+    )
   endif()
 
   # This needs to be available for the pybind11_extension function
-  set(PYTHON_MODULE_EXTENSION
-      "${_PYTHON_MODULE_EXTENSION}"
-      CACHE INTERNAL "")
+  if(NOT DEFINED PYTHON_MODULE_DEBUG_POSTFIX)
+    get_filename_component(_PYTHON_MODULE_DEBUG_POSTFIX "${_PYTHON_MODULE_EXT_SUFFIX}" NAME_WE)
+    set(PYTHON_MODULE_DEBUG_POSTFIX
+        "${_PYTHON_MODULE_DEBUG_POSTFIX}"
+        CACHE INTERNAL "")
+  endif()
+
+  if(NOT DEFINED PYTHON_MODULE_EXTENSION)
+    get_filename_component(_PYTHON_MODULE_EXTENSION "${_PYTHON_MODULE_EXT_SUFFIX}" EXT)
+    set(PYTHON_MODULE_EXTENSION
+        "${_PYTHON_MODULE_EXTENSION}"
+        CACHE INTERNAL "")
+  endif()
 endif()
 
 # Python debug libraries expose slightly different objects before 3.8
@@ -253,6 +264,9 @@ endfunction()
 
 function(pybind11_extension name)
   # The extension is precomputed
-  set_target_properties(${name} PROPERTIES PREFIX "" SUFFIX "${PYTHON_MODULE_EXTENSION}")
-
+  set_target_properties(
+    ${name}
+    PROPERTIES PREFIX ""
+               DEBUG_POSTFIX "${PYTHON_MODULE_DEBUG_POSTFIX}"
+               SUFFIX "${PYTHON_MODULE_EXTENSION}")
 endfunction()
diff --git a/tools/pybind11Tools.cmake b/tools/pybind11Tools.cmake
index 67e710bda5e..1b1774d09ef 100644
--- a/tools/pybind11Tools.cmake
+++ b/tools/pybind11Tools.cmake
@@ -65,6 +65,7 @@ _pybind11_promote_to_cache(PYTHON_INCLUDE_DIRS)
 _pybind11_promote_to_cache(PYTHON_LIBRARIES)
 _pybind11_promote_to_cache(PYTHON_MODULE_PREFIX)
 _pybind11_promote_to_cache(PYTHON_MODULE_EXTENSION)
+_pybind11_promote_to_cache(PYTHON_MODULE_DEBUG_POSTFIX)
 _pybind11_promote_to_cache(PYTHON_VERSION_MAJOR)
 _pybind11_promote_to_cache(PYTHON_VERSION_MINOR)
 _pybind11_promote_to_cache(PYTHON_VERSION)
@@ -148,8 +149,11 @@ endif()
 
 function(pybind11_extension name)
   # The prefix and extension are provided by FindPythonLibsNew.cmake
-  set_target_properties(${name} PROPERTIES PREFIX "${PYTHON_MODULE_PREFIX}"
-                                           SUFFIX "${PYTHON_MODULE_EXTENSION}")
+  set_target_properties(
+    ${name}
+    PROPERTIES PREFIX "${PYTHON_MODULE_PREFIX}"
+               DEBUG_POSTFIX "${PYTHON_MODULE_DEBUG_POSTFIX}"
+               SUFFIX "${PYTHON_MODULE_EXTENSION}")
 endfunction()
 
 # Build a Python extension module: