diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index 388640192..271c1019f 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -18,6 +18,7 @@ repos:
   hooks:
   - id: pyupgrade
     args: ["--py37-plus"]
+    exclude: ^cibuildwheel/resources/.*py$
 
 # Autoremoves unused imports
 - repo: https://github.com/hadialqattan/pycln
@@ -31,6 +32,8 @@ repos:
   rev: 5.10.1
   hooks:
   - id: isort
+    args: ["-a", "from __future__ import annotations"]
+    exclude: ^cibuildwheel/resources/.*py$
 
 - repo: https://github.com/psf/black
   rev: 22.6.0
diff --git a/bin/run_tests.py b/bin/run_tests.py
index 82e193c35..583d13c7a 100755
--- a/bin/run_tests.py
+++ b/bin/run_tests.py
@@ -1,5 +1,7 @@
 #!/usr/bin/env python3
 
+from __future__ import annotations
+
 import argparse
 import os
 import subprocess
diff --git a/bin/update_dependencies.py b/bin/update_dependencies.py
index 9dc9f5369..c0d7f2007 100755
--- a/bin/update_dependencies.py
+++ b/bin/update_dependencies.py
@@ -1,5 +1,7 @@
 #!/usr/bin/env python3
 
+from __future__ import annotations
+
 import os
 import shutil
 import subprocess
diff --git a/bin/update_readme_changelog.py b/bin/update_readme_changelog.py
index 90b2ffd8b..4a4625ff5 100755
--- a/bin/update_readme_changelog.py
+++ b/bin/update_readme_changelog.py
@@ -1,5 +1,7 @@
 #!/usr/bin/env python3
 
+from __future__ import annotations
+
 import re
 import sys
 from pathlib import Path
diff --git a/cibuildwheel/__init__.py b/cibuildwheel/__init__.py
index b4066b65a..b923f2287 100644
--- a/cibuildwheel/__init__.py
+++ b/cibuildwheel/__init__.py
@@ -1 +1,3 @@
+from __future__ import annotations
+
 __version__ = "2.8.1"
diff --git a/cibuildwheel/__main__.py b/cibuildwheel/__main__.py
index a3b7711f7..034673a20 100644
--- a/cibuildwheel/__main__.py
+++ b/cibuildwheel/__main__.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import argparse
 import os
 import shutil
@@ -7,7 +9,6 @@
 import textwrap
 from pathlib import Path
 from tempfile import mkdtemp
-from typing import List, Set, Union
 
 import cibuildwheel
 import cibuildwheel.linux
@@ -257,7 +258,7 @@ def build_in_directory(args: CommandLineArguments) -> None:
             log.warning(f"Can't delete temporary folder '{str(tmp_path)}'")
 
 
-def print_preamble(platform: str, options: Options, identifiers: List[str]) -> None:
+def print_preamble(platform: str, options: Options, identifiers: list[str]) -> None:
     print(
         textwrap.dedent(
             """
@@ -287,13 +288,13 @@ def print_preamble(platform: str, options: Options, identifiers: List[str]) -> N
 
 
 def get_build_identifiers(
-    platform: PlatformName, build_selector: BuildSelector, architectures: Set[Architecture]
-) -> List[str]:
-    python_configurations: Union[
-        List[cibuildwheel.linux.PythonConfiguration],
-        List[cibuildwheel.windows.PythonConfiguration],
-        List[cibuildwheel.macos.PythonConfiguration],
-    ]
+    platform: PlatformName, build_selector: BuildSelector, architectures: set[Architecture]
+) -> list[str]:
+    python_configurations: (
+        list[cibuildwheel.linux.PythonConfiguration]
+        | list[cibuildwheel.windows.PythonConfiguration]
+        | list[cibuildwheel.macos.PythonConfiguration]
+    )
 
     if platform == "linux":
         python_configurations = cibuildwheel.linux.get_python_configurations(
@@ -313,7 +314,7 @@ def get_build_identifiers(
     return [config.identifier for config in python_configurations]
 
 
-def detect_warnings(*, options: Options, identifiers: List[str]) -> List[str]:
+def detect_warnings(*, options: Options, identifiers: list[str]) -> list[str]:
     warnings = []
 
     # warn about deprecated {python} and {pip}
diff --git a/cibuildwheel/architecture.py b/cibuildwheel/architecture.py
index be87f3219..82a78b30b 100644
--- a/cibuildwheel/architecture.py
+++ b/cibuildwheel/architecture.py
@@ -1,8 +1,9 @@
+from __future__ import annotations
+
 import functools
 import platform as platform_module
 import re
 from enum import Enum
-from typing import Set
 
 from .typing import Final, Literal, PlatformName, assert_never
 
@@ -32,11 +33,11 @@ class Architecture(Enum):
     ARM64 = "ARM64"
 
     # Allow this to be sorted
-    def __lt__(self, other: "Architecture") -> bool:
+    def __lt__(self, other: Architecture) -> bool:
         return self.value < other.value
 
     @staticmethod
-    def parse_config(config: str, platform: PlatformName) -> "Set[Architecture]":
+    def parse_config(config: str, platform: PlatformName) -> set[Architecture]:
         result = set()
         for arch_str in re.split(r"[\s,]+", config):
             if arch_str == "auto":
@@ -54,7 +55,7 @@ def parse_config(config: str, platform: PlatformName) -> "Set[Architecture]":
         return result
 
     @staticmethod
-    def auto_archs(platform: PlatformName) -> "Set[Architecture]":
+    def auto_archs(platform: PlatformName) -> set[Architecture]:
         native_architecture = Architecture(platform_module.machine())
         result = {native_architecture}
 
@@ -72,7 +73,7 @@ def auto_archs(platform: PlatformName) -> "Set[Architecture]":
         return result
 
     @staticmethod
-    def all_archs(platform: PlatformName) -> "Set[Architecture]":
+    def all_archs(platform: PlatformName) -> set[Architecture]:
         all_archs_map = {
             "linux": {
                 Architecture.x86_64,
@@ -87,7 +88,7 @@ def all_archs(platform: PlatformName) -> "Set[Architecture]":
         return all_archs_map[platform]
 
     @staticmethod
-    def bitness_archs(platform: PlatformName, bitness: Literal["64", "32"]) -> "Set[Architecture]":
+    def bitness_archs(platform: PlatformName, bitness: Literal["64", "32"]) -> set[Architecture]:
         archs_32 = {Architecture.i686, Architecture.x86}
         auto_archs = Architecture.auto_archs(platform)
 
@@ -101,7 +102,7 @@ def bitness_archs(platform: PlatformName, bitness: Literal["64", "32"]) -> "Set[
 
 def allowed_architectures_check(
     platform: PlatformName,
-    architectures: Set[Architecture],
+    architectures: set[Architecture],
 ) -> None:
 
     allowed_architectures = Architecture.all_archs(platform)
diff --git a/cibuildwheel/bashlex_eval.py b/cibuildwheel/bashlex_eval.py
index cd1fa563c..47e4aea3a 100644
--- a/cibuildwheel/bashlex_eval.py
+++ b/cibuildwheel/bashlex_eval.py
@@ -1,6 +1,8 @@
+from __future__ import annotations
+
 import subprocess
 from dataclasses import dataclass
-from typing import Callable, Dict, List, Optional, Sequence
+from typing import Callable, Dict, List, Sequence
 
 import bashlex
 
@@ -8,19 +10,19 @@
 EnvironmentExecutor = Callable[[List[str], Dict[str, str]], str]
 
 
-def local_environment_executor(command: List[str], env: Dict[str, str]) -> str:
+def local_environment_executor(command: list[str], env: dict[str, str]) -> str:
     return subprocess.run(command, env=env, text=True, stdout=subprocess.PIPE, check=True).stdout
 
 
 @dataclass(frozen=True)
 class NodeExecutionContext:
-    environment: Dict[str, str]
+    environment: dict[str, str]
     input: str
     executor: EnvironmentExecutor
 
 
 def evaluate(
-    value: str, environment: Dict[str, str], executor: Optional[EnvironmentExecutor] = None
+    value: str, environment: dict[str, str], executor: EnvironmentExecutor | None = None
 ) -> str:
     if not value:
         # empty string evaluates to empty string
@@ -101,7 +103,7 @@ def evaluate_nodes_as_compound_command(
 
 
 def evaluate_nodes_as_simple_command(
-    nodes: List[bashlex.ast.node], context: NodeExecutionContext
+    nodes: list[bashlex.ast.node], context: NodeExecutionContext
 ) -> str:
     command = [evaluate_node(part, context=context) for part in nodes]
     return context.executor(command, context.environment)
diff --git a/cibuildwheel/environment.py b/cibuildwheel/environment.py
index 3bf982d29..a544852a2 100644
--- a/cibuildwheel/environment.py
+++ b/cibuildwheel/environment.py
@@ -1,5 +1,7 @@
+from __future__ import annotations
+
 import dataclasses
-from typing import Any, Dict, List, Mapping, Optional, Sequence
+from typing import Any, Mapping, Sequence
 
 import bashlex
 
@@ -12,7 +14,7 @@ class EnvironmentParseError(Exception):
     pass
 
 
-def split_env_items(env_string: str) -> List[str]:
+def split_env_items(env_string: str) -> list[str]:
     """Splits space-separated variable assignments into a list of individual assignments.
 
     >>> split_env_items('VAR=abc')
@@ -47,8 +49,8 @@ class EnvironmentAssignment(Protocol):
     def evaluated_value(
         self,
         *,
-        environment: Dict[str, str],
-        executor: Optional[bashlex_eval.EnvironmentExecutor] = None,
+        environment: dict[str, str],
+        executor: bashlex_eval.EnvironmentExecutor | None = None,
     ) -> str:
         """Returns the value of this assignment, as evaluated in the environment"""
 
@@ -84,8 +86,8 @@ def __init__(self, assignment: str):
 
     def evaluated_value(
         self,
-        environment: Dict[str, str],
-        executor: Optional[bashlex_eval.EnvironmentExecutor] = None,
+        environment: dict[str, str],
+        executor: bashlex_eval.EnvironmentExecutor | None = None,
     ) -> str:
         return bashlex_eval.evaluate(self.value, environment=environment, executor=executor)
 
@@ -100,7 +102,7 @@ def __eq__(self, other: object) -> bool:
 
 @dataclasses.dataclass
 class ParsedEnvironment:
-    assignments: List[EnvironmentAssignment]
+    assignments: list[EnvironmentAssignment]
 
     def __init__(self, assignments: Sequence[EnvironmentAssignment]) -> None:
         self.assignments = list(assignments)
@@ -108,8 +110,8 @@ def __init__(self, assignments: Sequence[EnvironmentAssignment]) -> None:
     def as_dictionary(
         self,
         prev_environment: Mapping[str, str],
-        executor: Optional[bashlex_eval.EnvironmentExecutor] = None,
-    ) -> Dict[str, str]:
+        executor: bashlex_eval.EnvironmentExecutor | None = None,
+    ) -> dict[str, str]:
         environment = dict(**prev_environment)
 
         for assignment in self.assignments:
diff --git a/cibuildwheel/extra.py b/cibuildwheel/extra.py
index 60eecbad2..36389e6f7 100644
--- a/cibuildwheel/extra.py
+++ b/cibuildwheel/extra.py
@@ -2,8 +2,9 @@
 These are utilities for the `/bin` scripts, not for the `cibuildwheel` program.
 """
 
+from __future__ import annotations
+
 from io import StringIO
-from typing import Dict, List
 
 from .typing import Protocol
 
@@ -15,7 +16,7 @@ def __str__(self) -> str:
         ...
 
 
-def dump_python_configurations(inp: Dict[str, Dict[str, List[Dict[str, Printable]]]]) -> str:
+def dump_python_configurations(inp: dict[str, dict[str, list[dict[str, Printable]]]]) -> str:
     output = StringIO()
     for header, values in inp.items():
         output.write(f"[{header}]\n")
diff --git a/cibuildwheel/functools_cached_property_38.py b/cibuildwheel/functools_cached_property_38.py
index e1c45ac26..cbe4537af 100644
--- a/cibuildwheel/functools_cached_property_38.py
+++ b/cibuildwheel/functools_cached_property_38.py
@@ -1,5 +1,7 @@
+from __future__ import annotations
+
 from threading import RLock
-from typing import Any, Callable, Generic, Optional, Type, TypeVar, overload
+from typing import Any, Callable, Generic, TypeVar, overload
 
 __all__ = ["cached_property"]
 
@@ -11,11 +13,11 @@
 class cached_property(Generic[_T]):
     def __init__(self, func: Callable[[Any], _T]):
         self.func = func
-        self.attrname: Optional[str] = None
+        self.attrname: str | None = None
         self.__doc__ = func.__doc__
         self.lock = RLock()
 
-    def __set_name__(self, owner: Type[Any], name: str) -> None:
+    def __set_name__(self, owner: type[Any], name: str) -> None:
         if self.attrname is None:
             self.attrname = name
         elif name != self.attrname:
@@ -25,14 +27,14 @@ def __set_name__(self, owner: Type[Any], name: str) -> None:
             )
 
     @overload
-    def __get__(self, instance: None, owner: Optional[Type[Any]] = ...) -> "cached_property[_T]":
+    def __get__(self, instance: None, owner: type[Any] | None = ...) -> cached_property[_T]:
         ...
 
     @overload
-    def __get__(self, instance: object, owner: Optional[Type[Any]] = ...) -> _T:
+    def __get__(self, instance: object, owner: type[Any] | None = ...) -> _T:
         ...
 
-    def __get__(self, instance: Optional[object], owner: Optional[Type[Any]] = None) -> Any:
+    def __get__(self, instance: object | None, owner: type[Any] | None = None) -> Any:
         if instance is None:
             return self
         if self.attrname is None:
diff --git a/cibuildwheel/linux.py b/cibuildwheel/linux.py
index 57a7deee1..2a0ec43f8 100644
--- a/cibuildwheel/linux.py
+++ b/cibuildwheel/linux.py
@@ -1,9 +1,11 @@
+from __future__ import annotations
+
 import subprocess
 import sys
 import textwrap
 from dataclasses import dataclass
 from pathlib import Path, PurePath, PurePosixPath
-from typing import Iterator, List, Set, Tuple
+from typing import Iterator, Tuple
 
 from .architecture import Architecture
 from .logger import log
@@ -35,15 +37,15 @@ def path(self) -> PurePosixPath:
 
 @dataclass(frozen=True)
 class BuildStep:
-    platform_configs: List[PythonConfiguration]
+    platform_configs: list[PythonConfiguration]
     platform_tag: str
     container_image: str
 
 
 def get_python_configurations(
     build_selector: BuildSelector,
-    architectures: Set[Architecture],
-) -> List[PythonConfiguration]:
+    architectures: set[Architecture],
+) -> list[PythonConfiguration]:
 
     full_python_configs = read_python_configs("linux")
 
@@ -79,7 +81,7 @@ def container_image_for_python_configuration(config: PythonConfiguration, option
 
 
 def get_build_steps(
-    options: Options, python_configurations: List[PythonConfiguration]
+    options: Options, python_configurations: list[PythonConfiguration]
 ) -> Iterator[BuildStep]:
     """
     Groups PythonConfigurations into BuildSteps. Each BuildStep represents a
@@ -110,7 +112,7 @@ def get_build_steps(
 def build_in_container(
     *,
     options: Options,
-    platform_configs: List[PythonConfiguration],
+    platform_configs: list[PythonConfiguration],
     container: OCIContainer,
     container_project_path: PurePath,
     container_package_dir: PurePath,
@@ -140,13 +142,13 @@ def build_in_container(
         )
         container.call(["sh", "-c", before_all_prepared], env=env)
 
-    built_wheels: List[PurePosixPath] = []
+    built_wheels: list[PurePosixPath] = []
 
     for config in platform_configs:
         log.build_start(config.identifier)
         build_options = options.build_options(config.identifier)
 
-        dependency_constraint_flags: List[PathOrStr] = []
+        dependency_constraint_flags: list[PathOrStr] = []
 
         if build_options.dependency_constraints:
             constraints_file = build_options.dependency_constraints.get_for_python_version(
@@ -395,7 +397,7 @@ def build(options: Options, tmp_path: Path) -> None:  # pylint: disable=unused-a
             sys.exit(1)
 
 
-def _matches_prepared_command(error_cmd: List[str], command_template: str) -> bool:
+def _matches_prepared_command(error_cmd: list[str], command_template: str) -> bool:
     if len(error_cmd) < 3 or error_cmd[0:2] != ["sh", "-c"]:
         return False
     command_prefix = command_template.split("{", maxsplit=1)[0].strip()
diff --git a/cibuildwheel/logger.py b/cibuildwheel/logger.py
index 0a4be14d2..6f408b474 100644
--- a/cibuildwheel/logger.py
+++ b/cibuildwheel/logger.py
@@ -1,9 +1,11 @@
+from __future__ import annotations
+
 import codecs
 import os
 import re
 import sys
 import time
-from typing import IO, AnyStr, Optional, Union
+from typing import IO, AnyStr
 
 from cibuildwheel.typing import Final
 from cibuildwheel.util import CIProvider, detect_ci_provider
@@ -39,10 +41,10 @@ class Logger:
     fold_mode: str
     colors_enabled: bool
     unicode_enabled: bool
-    active_build_identifier: Optional[str] = None
-    build_start_time: Optional[float] = None
-    step_start_time: Optional[float] = None
-    active_fold_group_name: Optional[str] = None
+    active_build_identifier: str | None = None
+    build_start_time: float | None = None
+    step_start_time: float | None = None
+    active_fold_group_name: str | None = None
 
     def __init__(self) -> None:
         if sys.platform == "win32" and hasattr(sys.stdout, "reconfigure"):
@@ -120,7 +122,7 @@ def step_end(self, success: bool = True) -> None:
 
             self.step_start_time = None
 
-    def step_end_with_error(self, error: Union[BaseException, str]) -> None:
+    def step_end_with_error(self, error: BaseException | str) -> None:
         self.step_end(success=False)
         self.error(error)
 
@@ -131,7 +133,7 @@ def warning(self, message: str) -> None:
             c = self.colors
             print(f"{c.yellow}Warning{c.end}: {message}\n", file=sys.stderr)
 
-    def error(self, error: Union[BaseException, str]) -> None:
+    def error(self, error: BaseException | str) -> None:
         if self.fold_mode == "github":
             print(f"::error::{error}\n", file=sys.stderr)
         else:
@@ -174,11 +176,11 @@ def _fold_group_identifier(name: str) -> str:
         return identifier.lower()[:20]
 
     @property
-    def colors(self) -> "Colors":
+    def colors(self) -> Colors:
         return Colors(enabled=self.colors_enabled)
 
     @property
-    def symbols(self) -> "Symbols":
+    def symbols(self) -> Symbols:
         return Symbols(unicode=self.unicode_enabled)
 
 
diff --git a/cibuildwheel/macos.py b/cibuildwheel/macos.py
index beb4d32ea..6d56be20f 100644
--- a/cibuildwheel/macos.py
+++ b/cibuildwheel/macos.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import functools
 import os
 import platform
@@ -7,7 +9,7 @@
 import sys
 from dataclasses import dataclass
 from pathlib import Path
-from typing import Dict, List, Sequence, Set, Tuple, cast
+from typing import Sequence, Tuple, cast
 
 from filelock import FileLock
 
@@ -37,7 +39,7 @@
 )
 
 
-def get_macos_version() -> Tuple[int, int]:
+def get_macos_version() -> tuple[int, int]:
     """
     Returns the macOS major/minor version, as a tuple, e.g. (10, 15) or (11, 0)
 
@@ -51,7 +53,7 @@ def get_macos_version() -> Tuple[int, int]:
     return cast(Tuple[int, int], version)
 
 
-def get_macos_sdks() -> List[str]:
+def get_macos_sdks() -> list[str]:
     output = call("xcodebuild", "-showsdks", capture_stdout=True)
     return [m.group(1) for m in re.finditer(r"-sdk (macosx\S+)", output)]
 
@@ -64,8 +66,8 @@ class PythonConfiguration:
 
 
 def get_python_configurations(
-    build_selector: BuildSelector, architectures: Set[Architecture]
-) -> List[PythonConfiguration]:
+    build_selector: BuildSelector, architectures: set[Architecture]
+) -> list[PythonConfiguration]:
 
     full_python_configs = read_python_configs("macos")
 
@@ -134,7 +136,7 @@ def setup_python(
     dependency_constraint_flags: Sequence[PathOrStr],
     environment: ParsedEnvironment,
     build_frontend: BuildFrontend,
-) -> Dict[str, str]:
+) -> dict[str, str]:
     tmp.mkdir()
     implementation_id = python_configuration.identifier.split("-")[0]
     log.step(f"Installing Python {implementation_id}...")
@@ -295,7 +297,7 @@ def build(options: Options, tmp_path: Path) -> None:
             )
             shell(before_all_prepared, env=env)
 
-        built_wheels: List[Path] = []
+        built_wheels: list[Path] = []
 
         for config in python_configurations:
             build_options = options.build_options(config.identifier)
@@ -418,7 +420,7 @@ def build(options: Options, tmp_path: Path) -> None:
 
             if build_options.test_command and build_options.test_selector(config.identifier):
                 machine_arch = platform.machine()
-                testing_archs: List[Literal["x86_64", "arm64"]]
+                testing_archs: list[Literal["x86_64", "arm64"]]
 
                 if config_is_arm64:
                     testing_archs = ["arm64"]
diff --git a/cibuildwheel/oci_container.py b/cibuildwheel/oci_container.py
index c02f76788..91714c7e1 100644
--- a/cibuildwheel/oci_container.py
+++ b/cibuildwheel/oci_container.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import io
 import json
 import os
@@ -9,7 +11,7 @@
 import uuid
 from pathlib import Path, PurePath, PurePosixPath
 from types import TracebackType
-from typing import IO, Dict, List, Optional, Sequence, Type, cast
+from typing import IO, Dict, Sequence, cast
 
 from cibuildwheel.util import CIProvider, detect_ci_provider
 
@@ -52,7 +54,7 @@ def __init__(
         *,
         image: str,
         simulate_32_bit: bool = False,
-        cwd: Optional[PathOrStr] = None,
+        cwd: PathOrStr | None = None,
         engine: ContainerEngine = "docker",
     ):
         if not image:
@@ -61,10 +63,10 @@ def __init__(
         self.image = image
         self.simulate_32_bit = simulate_32_bit
         self.cwd = cwd
-        self.name: Optional[str] = None
+        self.name: str | None = None
         self.engine = engine
 
-    def __enter__(self) -> "OCIContainer":
+    def __enter__(self) -> OCIContainer:
 
         self.name = f"cibuildwheel-{uuid.uuid4()}"
 
@@ -122,9 +124,9 @@ def __enter__(self) -> "OCIContainer":
 
     def __exit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc_val: Optional[BaseException],
-        exc_tb: Optional[TracebackType],
+        exc_type: type[BaseException] | None,
+        exc_val: BaseException | None,
+        exc_tb: TracebackType | None,
     ) -> None:
 
         self.bash_stdin.write(b"exit 0\n")
@@ -217,7 +219,7 @@ def copy_out(self, from_path: PurePath, to_path: Path) -> None:
         else:
             raise KeyError(self.engine)
 
-    def glob(self, path: PurePosixPath, pattern: str) -> List[PurePosixPath]:
+    def glob(self, path: PurePosixPath, pattern: str) -> list[PurePosixPath]:
         glob_pattern = path.joinpath(pattern)
 
         path_strings = json.loads(
@@ -236,9 +238,9 @@ def glob(self, path: PurePosixPath, pattern: str) -> List[PurePosixPath]:
     def call(
         self,
         args: Sequence[PathOrStr],
-        env: Optional[Dict[str, str]] = None,
+        env: dict[str, str] | None = None,
         capture_output: bool = False,
-        cwd: Optional[PathOrStr] = None,
+        cwd: PathOrStr | None = None,
     ) -> str:
 
         if cwd is None:
@@ -314,7 +316,7 @@ def call(
 
         return output
 
-    def get_environment(self) -> Dict[str, str]:
+    def get_environment(self) -> dict[str, str]:
         env = json.loads(
             self.call(
                 [
@@ -327,7 +329,7 @@ def get_environment(self) -> Dict[str, str]:
         )
         return cast(Dict[str, str], env)
 
-    def environment_executor(self, command: List[str], environment: Dict[str, str]) -> str:
+    def environment_executor(self, command: list[str], environment: dict[str, str]) -> str:
         # used as an EnvironmentExecutor to evaluate commands and capture output
         return self.call(command, env=environment, capture_output=True)
 
diff --git a/cibuildwheel/options.py b/cibuildwheel/options.py
index 59ff12269..308036042 100644
--- a/cibuildwheel/options.py
+++ b/cibuildwheel/options.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import functools
 import os
 import sys
@@ -6,18 +8,7 @@
 from contextlib import contextmanager
 from dataclasses import asdict, dataclass
 from pathlib import Path
-from typing import (
-    Any,
-    Dict,
-    Generator,
-    List,
-    Mapping,
-    Optional,
-    Set,
-    Tuple,
-    Union,
-    cast,
-)
+from typing import Any, Dict, Generator, List, Mapping, Union, cast
 
 if sys.version_info >= (3, 11):
     import tomllib
@@ -50,7 +41,7 @@
 @dataclass
 class CommandLineArguments:
     platform: Literal["auto", "linux", "macos", "windows"]
-    archs: Optional[str]
+    archs: str | None
     output_dir: Path
     config_file: str
     package_dir: Path
@@ -65,7 +56,7 @@ class GlobalOptions:
     output_dir: Path
     build_selector: BuildSelector
     test_selector: TestSelector
-    architectures: Set[Architecture]
+    architectures: set[Architecture]
     container_engine: ContainerEngine
 
 
@@ -74,14 +65,14 @@ class BuildOptions:
     globals: GlobalOptions
     environment: ParsedEnvironment
     before_all: str
-    before_build: Optional[str]
+    before_build: str | None
     repair_command: str
-    manylinux_images: Optional[Dict[str, str]]
-    musllinux_images: Optional[Dict[str, str]]
-    dependency_constraints: Optional[DependencyConstraints]
-    test_command: Optional[str]
-    before_test: Optional[str]
-    test_requires: List[str]
+    manylinux_images: dict[str, str] | None
+    musllinux_images: dict[str, str] | None
+    dependency_constraints: DependencyConstraints | None
+    test_command: str | None
+    before_test: str | None
+    test_requires: list[str]
     test_extras: str
     build_verbosity: int
     build_frontend: BuildFrontend
@@ -103,7 +94,7 @@ def test_selector(self) -> TestSelector:
         return self.globals.test_selector
 
     @property
-    def architectures(self) -> Set[Architecture]:
+    def architectures(self) -> set[Architecture]:
         return self.globals.architectures
 
 
@@ -113,7 +104,7 @@ def architectures(self) -> Set[Architecture]:
 @dataclass(frozen=True)
 class Override:
     select_pattern: str
-    options: Dict[str, Setting]
+    options: dict[str, Setting]
 
 
 MANYLINUX_OPTIONS = {f"manylinux-{build_platform}-image" for build_platform in MANYLINUX_ARCHS}
@@ -134,7 +125,7 @@ class ConfigOptionError(KeyError):
     pass
 
 
-def _dig_first(*pairs: Tuple[Mapping[str, Setting], str], ignore_empty: bool = False) -> Setting:
+def _dig_first(*pairs: tuple[Mapping[str, Setting], str], ignore_empty: bool = False) -> Setting:
     """
     Return the first dict item that matches from pairs of dicts and keys.
     Will throw a KeyError if missing.
@@ -176,10 +167,10 @@ class OptionsReader:
 
     def __init__(
         self,
-        config_file_path: Optional[Path] = None,
+        config_file_path: Path | None = None,
         *,
         platform: PlatformName,
-        disallow: Optional[Dict[str, Set[str]]] = None,
+        disallow: dict[str, set[str]] | None = None,
     ) -> None:
         self.platform = platform
         self.disallow = disallow or {}
@@ -189,8 +180,8 @@ def __init__(
         self.default_options, self.default_platform_options = self._load_file(defaults_path)
 
         # Load the project config file
-        config_options: Dict[str, Any] = {}
-        config_platform_options: Dict[str, Any] = {}
+        config_options: dict[str, Any] = {}
+        config_platform_options: dict[str, Any] = {}
 
         if config_file_path is not None:
             config_options, config_platform_options = self._load_file(config_file_path)
@@ -209,8 +200,8 @@ def __init__(
         self.config_options = config_options
         self.config_platform_options = config_platform_options
 
-        self.overrides: List[Override] = []
-        self.current_identifier: Optional[str] = None
+        self.overrides: list[Override] = []
+        self.current_identifier: str | None = None
 
         config_overrides = self.config_options.get("overrides")
 
@@ -251,7 +242,7 @@ def _is_valid_platform_option(self, name: str) -> bool:
 
         return name in allowed_option_names
 
-    def _load_file(self, filename: Path) -> Tuple[Dict[str, Any], Dict[str, Any]]:
+    def _load_file(self, filename: Path) -> tuple[dict[str, Any], dict[str, Any]]:
         """
         Load a toml file, returns global and platform as separate dicts.
         """
@@ -264,7 +255,7 @@ def _load_file(self, filename: Path) -> Tuple[Dict[str, Any], Dict[str, Any]]:
         return global_options, platform_options
 
     @property
-    def active_config_overrides(self) -> List[Override]:
+    def active_config_overrides(self) -> list[Override]:
         if self.current_identifier is None:
             return []
         return [
@@ -272,7 +263,7 @@ def active_config_overrides(self) -> List[Override]:
         ]
 
     @contextmanager
-    def identifier(self, identifier: Optional[str]) -> Generator[None, None, None]:
+    def identifier(self, identifier: str | None) -> Generator[None, None, None]:
         self.current_identifier = identifier
         try:
             yield
@@ -284,8 +275,8 @@ def get(
         name: str,
         *,
         env_plat: bool = True,
-        sep: Optional[str] = None,
-        table: Optional[TableFmt] = None,
+        sep: str | None = None,
+        table: TableFmt | None = None,
         ignore_empty: bool = False,
     ) -> str:
         """
@@ -349,7 +340,7 @@ def __init__(self, platform: PlatformName, command_line_arguments: CommandLineAr
         )
 
     @property
-    def config_file_path(self) -> Optional[Path]:
+    def config_file_path(self) -> Path | None:
         args = self.command_line_arguments
 
         if args.config_file:
@@ -363,7 +354,7 @@ def config_file_path(self) -> Optional[Path]:
         return None
 
     @cached_property
-    def package_requires_python_str(self) -> Optional[str]:
+    def package_requires_python_str(self) -> str | None:
         args = self.command_line_arguments
         return get_requires_python_str(Path(args.package_dir))
 
@@ -383,7 +374,7 @@ def globals(self) -> GlobalOptions:
 
         # This is not supported in tool.cibuildwheel, as it comes from a standard location.
         # Passing this in as an environment variable will override pyproject.toml, setup.cfg, or setup.py
-        requires_python_str: Optional[str] = (
+        requires_python_str: str | None = (
             os.environ.get("CIBW_PROJECT_REQUIRES_PYTHON") or self.package_requires_python_str
         )
         requires_python = None if requires_python_str is None else SpecifierSet(requires_python_str)
@@ -417,7 +408,7 @@ def globals(self) -> GlobalOptions:
             container_engine=container_engine,
         )
 
-    def build_options(self, identifier: Optional[str]) -> BuildOptions:
+    def build_options(self, identifier: str | None) -> BuildOptions:
         """
         Compute BuildOptions for a single run configuration.
         """
@@ -469,9 +460,9 @@ def build_options(self, identifier: Optional[str]) -> BuildOptions:
                         pass
 
             if dependency_versions == "pinned":
-                dependency_constraints: Optional[
+                dependency_constraints: None | (
                     DependencyConstraints
-                ] = DependencyConstraints.with_defaults()
+                ) = DependencyConstraints.with_defaults()
             elif dependency_versions == "latest":
                 dependency_constraints = None
             else:
@@ -486,8 +477,8 @@ def build_options(self, identifier: Optional[str]) -> BuildOptions:
             except ValueError:
                 build_verbosity = 0
 
-            manylinux_images: Dict[str, str] = {}
-            musllinux_images: Dict[str, str] = {}
+            manylinux_images: dict[str, str] = {}
+            musllinux_images: dict[str, str] = {}
             if self.platform == "linux":
                 all_pinned_container_images = _get_pinned_container_images()
 
@@ -539,7 +530,7 @@ def build_options(self, identifier: Optional[str]) -> BuildOptions:
                 build_frontend=build_frontend,
             )
 
-    def check_for_invalid_configuration(self, identifiers: List[str]) -> None:
+    def check_for_invalid_configuration(self, identifiers: list[str]) -> None:
         if self.platform in ["macos", "windows"]:
             before_all_values = {self.build_options(i).before_all for i in identifiers}
 
@@ -562,7 +553,7 @@ def check_for_deprecated_options(self) -> None:
         deprecated_selectors("CIBW_SKIP", build_selector.skip_config)
         deprecated_selectors("CIBW_TEST_SKIP", test_selector.skip_config)
 
-    def summary(self, identifiers: List[str]) -> str:
+    def summary(self, identifiers: list[str]) -> str:
         lines = [
             f"{option_name}: {option_value!r}"
             for option_name, option_value in sorted(asdict(self.globals).items())
diff --git a/cibuildwheel/projectfiles.py b/cibuildwheel/projectfiles.py
index 90d388f6b..b5c3cbdf2 100644
--- a/cibuildwheel/projectfiles.py
+++ b/cibuildwheel/projectfiles.py
@@ -1,8 +1,10 @@
+from __future__ import annotations
+
 import ast
 import sys
 from configparser import ConfigParser
 from pathlib import Path
-from typing import Any, Optional
+from typing import Any
 
 if sys.version_info >= (3, 11):
     import tomllib
@@ -24,7 +26,7 @@ def get_constant(x: ast.Constant) -> Any:
 
 class Analyzer(ast.NodeVisitor):
     def __init__(self) -> None:
-        self.requires_python: Optional[str] = None
+        self.requires_python: str | None = None
 
     def visit(self, node: ast.AST) -> None:
         for inner_node in ast.walk(node):
@@ -43,7 +45,7 @@ def visit_keyword(self, node: ast.keyword) -> None:
                 self.requires_python = get_constant(node.value)
 
 
-def setup_py_python_requires(content: str) -> Optional[str]:
+def setup_py_python_requires(content: str) -> str | None:
     try:
         tree = ast.parse(content)
         analyzer = Analyzer()
@@ -53,7 +55,7 @@ def setup_py_python_requires(content: str) -> Optional[str]:
         return None
 
 
-def get_requires_python_str(package_dir: Path) -> Optional[str]:
+def get_requires_python_str(package_dir: Path) -> str | None:
     """Return the python requires string from the most canonical source available, or None"""
 
     # Read in from pyproject.toml:project.requires-python
diff --git a/cibuildwheel/typing.py b/cibuildwheel/typing.py
index 1e6e57873..a546d7bf3 100644
--- a/cibuildwheel/typing.py
+++ b/cibuildwheel/typing.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import os
 import subprocess
 import sys
@@ -36,7 +38,7 @@
 
 
 PlatformName = Literal["linux", "macos", "windows"]
-PLATFORMS: Final[Set[PlatformName]] = {"linux", "macos", "windows"}
+PLATFORMS: Final[set[PlatformName]] = {"linux", "macos", "windows"}
 
 
 def assert_never(value: NoReturn) -> NoReturn:
diff --git a/cibuildwheel/util.py b/cibuildwheel/util.py
index d2287a056..6a6a6e2a4 100644
--- a/cibuildwheel/util.py
+++ b/cibuildwheel/util.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import contextlib
 import fnmatch
 import itertools
@@ -18,15 +20,11 @@
 from typing import (
     Any,
     ClassVar,
-    Dict,
     Generator,
     Iterable,
-    List,
-    Optional,
     Sequence,
     TextIO,
     TypeVar,
-    Union,
     cast,
     overload,
 )
@@ -98,8 +96,8 @@
 @overload
 def call(
     *args: PathOrStr,
-    env: Optional[Dict[str, str]] = None,
-    cwd: Optional[PathOrStr] = None,
+    env: dict[str, str] | None = None,
+    cwd: PathOrStr | None = None,
     capture_stdout: Literal[False] = ...,
 ) -> None:
     ...
@@ -108,8 +106,8 @@ def call(
 @overload
 def call(
     *args: PathOrStr,
-    env: Optional[Dict[str, str]] = None,
-    cwd: Optional[PathOrStr] = None,
+    env: dict[str, str] | None = None,
+    cwd: PathOrStr | None = None,
     capture_stdout: Literal[True],
 ) -> str:
     ...
@@ -117,10 +115,10 @@ def call(
 
 def call(
     *args: PathOrStr,
-    env: Optional[Dict[str, str]] = None,
-    cwd: Optional[PathOrStr] = None,
+    env: dict[str, str] | None = None,
+    cwd: PathOrStr | None = None,
     capture_stdout: bool = False,
-) -> Optional[str]:
+) -> str | None:
     """
     Run subprocess.run, but print the commands first. Takes the commands as
     *args. Uses shell=True on Windows due to a bug. Also converts to
@@ -130,7 +128,7 @@ def call(
     args_ = [str(arg) for arg in args]
     # print the command executing for the logs
     print("+ " + " ".join(shlex.quote(a) for a in args_))
-    kwargs: Dict[str, Any] = {}
+    kwargs: dict[str, Any] = {}
     if capture_stdout:
         kwargs["universal_newlines"] = True
         kwargs["stdout"] = subprocess.PIPE
@@ -140,9 +138,7 @@ def call(
     return cast(str, result.stdout)
 
 
-def shell(
-    *commands: str, env: Optional[Dict[str, str]] = None, cwd: Optional[PathOrStr] = None
-) -> None:
+def shell(*commands: str, env: dict[str, str] | None = None, cwd: PathOrStr | None = None) -> None:
     command = " ".join(commands)
     print(f"+ {command}")
     subprocess.run(command, env=env, cwd=cwd, shell=True, check=True)
@@ -200,7 +196,7 @@ def prepare_command(command: str, **kwargs: PathOrStr) -> str:
     return format_safe(command, python="python", pip="pip", **kwargs)
 
 
-def get_build_verbosity_extra_flags(level: int) -> List[str]:
+def get_build_verbosity_extra_flags(level: int) -> list[str]:
     if level > 0:
         return ["-" + level * "v"]
     elif level < 0:
@@ -209,11 +205,11 @@ def get_build_verbosity_extra_flags(level: int) -> List[str]:
         return []
 
 
-def read_python_configs(config: PlatformName) -> List[Dict[str, str]]:
+def read_python_configs(config: PlatformName) -> list[dict[str, str]]:
     input_file = resources_dir / "build-platforms.toml"
     with input_file.open("rb") as f:
         loaded_file = tomllib.load(f)
-    results: List[Dict[str, str]] = list(loaded_file[config]["python_configurations"])
+    results: list[dict[str, str]] = list(loaded_file[config]["python_configurations"])
     return results
 
 
@@ -243,7 +239,7 @@ class BuildSelector:
 
     build_config: str
     skip_config: str
-    requires_python: Optional[SpecifierSet] = None
+    requires_python: SpecifierSet | None = None
 
     # a pattern that skips prerelease versions, when include_prereleases is False.
     PRERELEASE_SKIP: ClassVar[str] = "cp311-*"
@@ -328,7 +324,7 @@ def __init__(self, base_file_path: Path):
         self.base_file_path = base_file_path.resolve()
 
     @staticmethod
-    def with_defaults() -> "DependencyConstraints":
+    def with_defaults() -> DependencyConstraints:
         return DependencyConstraints(base_file_path=resources_dir / "constraints.txt")
 
     def get_for_python_version(self, version: str) -> Path:
@@ -400,7 +396,7 @@ class CIProvider(Enum):
     other = "other"
 
 
-def detect_ci_provider() -> Optional[CIProvider]:
+def detect_ci_provider() -> CIProvider | None:
     if "TRAVIS" in os.environ:
         return CIProvider.travis_ci
     elif "APPVEYOR" in os.environ:
@@ -473,7 +469,7 @@ def print_new_wheels(msg: str, output_dir: Path) -> Generator[None, None, None]:
     )
 
 
-def get_pip_version(env: Dict[str, str]) -> str:
+def get_pip_version(env: dict[str, str]) -> str:
     versions_output_text = call(
         "python", "-m", "pip", "freeze", "--all", capture_stdout=True, env=env
     )
@@ -501,7 +497,7 @@ def _ensure_virtualenv() -> Path:
 
 def _parse_constraints_for_virtualenv(
     dependency_constraint_flags: Sequence[PathOrStr],
-) -> Dict[str, str]:
+) -> dict[str, str]:
     """
     Parses the constraints file referenced by `dependency_constraint_flags` and returns a dict where
     the key is the package name, and the value is the constraint version.
@@ -547,7 +543,7 @@ def _parse_constraints_for_virtualenv(
 
 def virtualenv(
     python: Path, venv_path: Path, dependency_constraint_flags: Sequence[PathOrStr]
-) -> Dict[str, str]:
+) -> dict[str, str]:
     assert python.exists()
     virtualenv_app = _ensure_virtualenv()
     constraints = _parse_constraints_for_virtualenv(dependency_constraint_flags)
@@ -589,7 +585,7 @@ def virtualenv(
 T = TypeVar("T", bound=PurePath)
 
 
-def find_compatible_wheel(wheels: Sequence[T], identifier: str) -> Optional[T]:
+def find_compatible_wheel(wheels: Sequence[T], identifier: str) -> T | None:
     """
     Finds a wheel with an abi3 or a none ABI tag in `wheels` compatible with the Python interpreter
     specified by `identifier` that is previously built.
@@ -641,7 +637,7 @@ def find_compatible_wheel(wheels: Sequence[T], identifier: str) -> Optional[T]:
 
 # Can be replaced by contextlib.chdir in Python 3.11
 @contextlib.contextmanager
-def chdir(new_path: Union[Path, str]) -> Generator[None, None, None]:
+def chdir(new_path: Path | str) -> Generator[None, None, None]:
     """Non thread-safe context manager to change the current working directory."""
 
     cwd = os.getcwd()
diff --git a/cibuildwheel/windows.py b/cibuildwheel/windows.py
index 82309a232..b6e223ec5 100644
--- a/cibuildwheel/windows.py
+++ b/cibuildwheel/windows.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import os
 import shutil
 import subprocess
@@ -5,7 +7,7 @@
 from dataclasses import dataclass
 from functools import lru_cache
 from pathlib import Path
-from typing import Dict, List, Optional, Sequence, Set
+from typing import Sequence
 from zipfile import ZipFile
 
 from filelock import FileLock
@@ -34,7 +36,7 @@
 )
 
 
-def get_nuget_args(version: str, arch: str, output_directory: Path) -> List[str]:
+def get_nuget_args(version: str, arch: str, output_directory: Path) -> list[str]:
     platform_suffix = {"32": "x86", "64": "", "ARM64": "arm64"}
     python_name = "python" + platform_suffix[arch]
     return [
@@ -53,13 +55,13 @@ class PythonConfiguration:
     version: str
     arch: str
     identifier: str
-    url: Optional[str] = None
+    url: str | None = None
 
 
 def get_python_configurations(
     build_selector: BuildSelector,
-    architectures: Set[Architecture],
-) -> List[PythonConfiguration]:
+    architectures: set[Architecture],
+) -> list[PythonConfiguration]:
 
     full_python_configs = read_python_configs("windows")
 
@@ -124,7 +126,7 @@ def setup_python(
     dependency_constraint_flags: Sequence[PathOrStr],
     environment: ParsedEnvironment,
     build_frontend: BuildFrontend,
-) -> Dict[str, str]:
+) -> dict[str, str]:
     tmp.mkdir()
     implementation_id = python_configuration.identifier.split("-")[0]
     log.step(f"Installing Python {implementation_id}...")
@@ -253,7 +255,7 @@ def build(options: Options, tmp_path: Path) -> None:
             )
             shell(before_all_prepared, env=env)
 
-        built_wheels: List[Path] = []
+        built_wheels: list[Path] = []
 
         for config in python_configurations:
             build_options = options.build_options(config.identifier)
diff --git a/docs/main.py b/docs/main.py
index b17982372..acb0d49cd 100644
--- a/docs/main.py
+++ b/docs/main.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import subprocess
 from typing import Any
 
diff --git a/noxfile.py b/noxfile.py
index f045e616f..659e7ff52 100644
--- a/noxfile.py
+++ b/noxfile.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import os
 import shutil
 import sys
diff --git a/setup.py b/setup.py
index 6c08425d8..0cb950285 100644
--- a/setup.py
+++ b/setup.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 from setuptools import setup
 
 extras = {
diff --git a/test/conftest.py b/test/conftest.py
index e7c421123..872eeb172 100644
--- a/test/conftest.py
+++ b/test/conftest.py
@@ -1,4 +1,4 @@
-from typing import Dict
+from __future__ import annotations
 
 import pytest
 
@@ -13,5 +13,5 @@ def pytest_addoption(parser) -> None:
 @pytest.fixture(
     params=[{"CIBW_BUILD_FRONTEND": "pip"}, {"CIBW_BUILD_FRONTEND": "build"}], ids=["pip", "build"]
 )
-def build_frontend_env(request) -> Dict[str, str]:
+def build_frontend_env(request) -> dict[str, str]:
     return request.param  # type: ignore[no-any-return]
diff --git a/test/test_0_basic.py b/test/test_0_basic.py
index 2d2e8d97f..5fb7a2410 100644
--- a/test/test_0_basic.py
+++ b/test/test_0_basic.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import textwrap
 
 import pytest
diff --git a/test/test_abi_variants.py b/test/test_abi_variants.py
index 932a2ec01..114736553 100644
--- a/test/test_abi_variants.py
+++ b/test/test_abi_variants.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import textwrap
 
 from . import test_projects, utils
diff --git a/test/test_before_all.py b/test/test_before_all.py
index 9c8722d72..bad2d4c0f 100644
--- a/test/test_before_all.py
+++ b/test/test_before_all.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import subprocess
 import textwrap
 
diff --git a/test/test_before_build.py b/test/test_before_build.py
index 00906acc1..1ee7757e4 100644
--- a/test/test_before_build.py
+++ b/test/test_before_build.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import subprocess
 import textwrap
 
diff --git a/test/test_before_test.py b/test/test_before_test.py
index 535131aa0..5c3e09d2b 100644
--- a/test/test_before_test.py
+++ b/test/test_before_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 from . import test_projects, utils
 
 before_test_project = test_projects.new_c_project()
diff --git a/test/test_build_skip.py b/test/test_build_skip.py
index 0d285d822..e29d14f10 100644
--- a/test/test_build_skip.py
+++ b/test/test_build_skip.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import textwrap
 
 from . import test_projects, utils
diff --git a/test/test_container_images.py b/test/test_container_images.py
index 8318a64ea..75b102e38 100644
--- a/test/test_container_images.py
+++ b/test/test_container_images.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import platform
 import textwrap
 
diff --git a/test/test_cpp_standards.py b/test/test_cpp_standards.py
index a5385007f..f09e7a530 100644
--- a/test/test_cpp_standards.py
+++ b/test/test_cpp_standards.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import os
 
 import jinja2
diff --git a/test/test_dependency_versions.py b/test/test_dependency_versions.py
index 90854a866..e1f206324 100644
--- a/test/test_dependency_versions.py
+++ b/test/test_dependency_versions.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import re
 import textwrap
 
diff --git a/test/test_emulation.py b/test/test_emulation.py
index 95b574dd7..6b29c019b 100644
--- a/test/test_emulation.py
+++ b/test/test_emulation.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import subprocess
 
 import pytest
diff --git a/test/test_environment.py b/test/test_environment.py
index 6ad8ff9f4..4382df44e 100644
--- a/test/test_environment.py
+++ b/test/test_environment.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import os
 import subprocess
 import textwrap
diff --git a/test/test_from_sdist.py b/test/test_from_sdist.py
index d1d4ff115..f0b7e93e8 100644
--- a/test/test_from_sdist.py
+++ b/test/test_from_sdist.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import os
 import subprocess
 import sys
diff --git a/test/test_macos_archs.py b/test/test_macos_archs.py
index a85a6b245..d3a56fb7a 100644
--- a/test/test_macos_archs.py
+++ b/test/test_macos_archs.py
@@ -1,6 +1,7 @@
+from __future__ import annotations
+
 import platform
 import subprocess
-from typing import Tuple
 
 import pytest
 
@@ -14,7 +15,7 @@
 }
 
 
-def get_xcode_version() -> Tuple[int, int]:
+def get_xcode_version() -> tuple[int, int]:
     output = subprocess.run(
         ["xcodebuild", "-version"],
         text=True,
diff --git a/test/test_manylinuxXXXX_only.py b/test/test_manylinuxXXXX_only.py
index 935aa5925..6013e856f 100644
--- a/test/test_manylinuxXXXX_only.py
+++ b/test/test_manylinuxXXXX_only.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import platform
 import textwrap
 
diff --git a/test/test_pep518.py b/test/test_pep518.py
index 128834280..0f1bc0c55 100644
--- a/test/test_pep518.py
+++ b/test/test_pep518.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import textwrap
 
 from . import test_projects, utils
diff --git a/test/test_podman.py b/test/test_podman.py
index dd07572b7..ea3bd8a69 100644
--- a/test/test_podman.py
+++ b/test/test_podman.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import pytest
 
 from . import test_projects, utils
diff --git a/test/test_projects/__init__.py b/test/test_projects/__init__.py
index d6bed8189..2d8da665b 100644
--- a/test/test_projects/__init__.py
+++ b/test/test_projects/__init__.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 from .base import TestProject
 from .c import new_c_project
 
diff --git a/test/test_projects/__main__.py b/test/test_projects/__main__.py
index a1e77c432..0d3cf2520 100644
--- a/test/test_projects/__main__.py
+++ b/test/test_projects/__main__.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import importlib
 import subprocess
 import sys
diff --git a/test/test_projects/base.py b/test/test_projects/base.py
index 66d0006ed..c4ea54039 100644
--- a/test/test_projects/base.py
+++ b/test/test_projects/base.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 from pathlib import Path
 from typing import Any, Dict, Union
 
diff --git a/test/test_projects/c.py b/test/test_projects/c.py
index d4c37c694..62252a620 100644
--- a/test/test_projects/c.py
+++ b/test/test_projects/c.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import jinja2
 
 from .base import TestProject
diff --git a/test/test_pure_wheel.py b/test/test_pure_wheel.py
index 2ba33711f..f7a4807bd 100644
--- a/test/test_pure_wheel.py
+++ b/test/test_pure_wheel.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import subprocess
 from test import test_projects
 
diff --git a/test/test_same_wheel.py b/test/test_same_wheel.py
index d89f28cb7..f25cba5da 100644
--- a/test/test_same_wheel.py
+++ b/test/test_same_wheel.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import subprocess
 from test import test_projects
 
diff --git a/test/test_ssl.py b/test/test_ssl.py
index 5283a59d4..9c35650eb 100644
--- a/test/test_ssl.py
+++ b/test/test_ssl.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import textwrap
 
 from . import test_projects, utils
diff --git a/test/test_subdir_package.py b/test/test_subdir_package.py
index 9241ae30f..c1d73df1a 100644
--- a/test/test_subdir_package.py
+++ b/test/test_subdir_package.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 from pathlib import Path
 
 import jinja2
diff --git a/test/test_testing.py b/test/test_testing.py
index ef41f35a5..c7264383c 100644
--- a/test/test_testing.py
+++ b/test/test_testing.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import os
 import subprocess
 import textwrap
diff --git a/test/test_troubleshooting.py b/test/test_troubleshooting.py
index 7039c2687..e647bca69 100644
--- a/test/test_troubleshooting.py
+++ b/test/test_troubleshooting.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import subprocess
 
 import pytest
diff --git a/test/test_wheel_tag.py b/test/test_wheel_tag.py
index a026b2d77..786eaa7ac 100644
--- a/test/test_wheel_tag.py
+++ b/test/test_wheel_tag.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import pytest
 
 from . import test_projects, utils
diff --git a/test/utils.py b/test/utils.py
index ebe682e37..947c89689 100644
--- a/test/utils.py
+++ b/test/utils.py
@@ -4,6 +4,8 @@
 This file is added to the PYTHONPATH in the test runner at bin/run_test.py.
 """
 
+from __future__ import annotations
+
 import os
 import platform as pm
 import subprocess
diff --git a/unit_test/build_ids_test.py b/unit_test/build_ids_test.py
index 60ac38748..0f62ba408 100644
--- a/unit_test/build_ids_test.py
+++ b/unit_test/build_ids_test.py
@@ -1,5 +1,6 @@
+from __future__ import annotations
+
 import sys
-from typing import Dict, List
 
 if sys.version_info >= (3, 11):
     import tomllib
@@ -27,7 +28,7 @@ def test_compare_configs():
 
 def test_dump_with_Version():
     # MyPy doesn't understand deeply nested dicts correctly
-    example: Dict[str, Dict[str, List[Dict[str, Printable]]]] = {
+    example: dict[str, dict[str, list[dict[str, Printable]]]] = {
         "windows": {
             "python_configurations": [
                 {"identifier": "cp27-win32", "version": Version("2.7.18"), "arch": "32"},
diff --git a/unit_test/build_selector_test.py b/unit_test/build_selector_test.py
index b71cb05f8..14ff8da63 100644
--- a/unit_test/build_selector_test.py
+++ b/unit_test/build_selector_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 from packaging.specifiers import SpecifierSet
 
 from cibuildwheel.util import BuildSelector
diff --git a/unit_test/conftest.py b/unit_test/conftest.py
index 3d98c30b0..7e1df1b2c 100644
--- a/unit_test/conftest.py
+++ b/unit_test/conftest.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import sys
 from pathlib import Path
 
diff --git a/unit_test/dependency_constraints_test.py b/unit_test/dependency_constraints_test.py
index 952151958..ce907d5e3 100644
--- a/unit_test/dependency_constraints_test.py
+++ b/unit_test/dependency_constraints_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 from pathlib import Path
 
 from cibuildwheel.util import DependencyConstraints
diff --git a/unit_test/download_test.py b/unit_test/download_test.py
index 0aac14309..efc5c4e5b 100644
--- a/unit_test/download_test.py
+++ b/unit_test/download_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import ssl
 
 import certifi
diff --git a/unit_test/environment_test.py b/unit_test/environment_test.py
index c1d0a4a1d..386787712 100644
--- a/unit_test/environment_test.py
+++ b/unit_test/environment_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import os
 
 from cibuildwheel.environment import parse_environment
diff --git a/unit_test/linux_build_steps_test.py b/unit_test/linux_build_steps_test.py
index 36aaebb70..809cdf650 100644
--- a/unit_test/linux_build_steps_test.py
+++ b/unit_test/linux_build_steps_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import textwrap
 from pathlib import Path
 from pprint import pprint
diff --git a/unit_test/main_tests/conftest.py b/unit_test/main_tests/conftest.py
index 973012cfb..257321873 100644
--- a/unit_test/main_tests/conftest.py
+++ b/unit_test/main_tests/conftest.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import contextlib
 import platform as platform_module
 import subprocess
diff --git a/unit_test/main_tests/main_options_test.py b/unit_test/main_tests/main_options_test.py
index 59368de5b..813fd5c56 100644
--- a/unit_test/main_tests/main_options_test.py
+++ b/unit_test/main_tests/main_options_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import sys
 from fnmatch import fnmatch
 from pathlib import Path
diff --git a/unit_test/main_tests/main_platform_test.py b/unit_test/main_tests/main_platform_test.py
index 8974a27ec..61dd8e850 100644
--- a/unit_test/main_tests/main_platform_test.py
+++ b/unit_test/main_tests/main_platform_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import sys
 
 import pytest
diff --git a/unit_test/main_tests/main_requires_python_test.py b/unit_test/main_tests/main_requires_python_test.py
index 0edb09375..e513f7436 100644
--- a/unit_test/main_tests/main_requires_python_test.py
+++ b/unit_test/main_tests/main_requires_python_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import sys
 import textwrap
 
diff --git a/unit_test/oci_container_test.py b/unit_test/oci_container_test.py
index 05ef24fd1..30739db72 100644
--- a/unit_test/oci_container_test.py
+++ b/unit_test/oci_container_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import os
 import platform
 import random
diff --git a/unit_test/option_prepare_test.py b/unit_test/option_prepare_test.py
index 3eef68a77..bc01317b3 100644
--- a/unit_test/option_prepare_test.py
+++ b/unit_test/option_prepare_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import platform as platform_module
 import subprocess
 import sys
diff --git a/unit_test/options_test.py b/unit_test/options_test.py
index 3ce8b2147..a609bb492 100644
--- a/unit_test/options_test.py
+++ b/unit_test/options_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import platform as platform_module
 
 import pytest
diff --git a/unit_test/options_toml_test.py b/unit_test/options_toml_test.py
index 1dcfdc212..a3fab2cc8 100644
--- a/unit_test/options_toml_test.py
+++ b/unit_test/options_toml_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 from pathlib import Path
 
 import pytest
diff --git a/unit_test/projectfiles_test.py b/unit_test/projectfiles_test.py
index 6c55d46a1..e7e21ba5d 100644
--- a/unit_test/projectfiles_test.py
+++ b/unit_test/projectfiles_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 from textwrap import dedent
 
 from cibuildwheel.projectfiles import get_requires_python_str, setup_py_python_requires
diff --git a/unit_test/utils.py b/unit_test/utils.py
index 2b312ecad..0cd2fefb3 100644
--- a/unit_test/utils.py
+++ b/unit_test/utils.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 from pathlib import Path
 
 from cibuildwheel.options import CommandLineArguments
diff --git a/unit_test/utils_test.py b/unit_test/utils_test.py
index 7f949a739..adf214358 100644
--- a/unit_test/utils_test.py
+++ b/unit_test/utils_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 from pathlib import PurePath
 
 import pytest
diff --git a/unit_test/wheel_print_test.py b/unit_test/wheel_print_test.py
index 020600604..fe68f7181 100644
--- a/unit_test/wheel_print_test.py
+++ b/unit_test/wheel_print_test.py
@@ -1,3 +1,5 @@
+from __future__ import annotations
+
 import pytest
 
 from cibuildwheel.util import print_new_wheels