diff --git a/.cirrus.yml b/.cirrus.yml
index 6faa9bf56..6c13ee1a7 100644
--- a/.cirrus.yml
+++ b/.cirrus.yml
@@ -7,7 +7,6 @@ run_tests: &RUN_TESTS
   run_cibuildwheel_tests_script:
     - python ./bin/run_tests.py
 
-
 linux_x86_task:
   timeout_in: 120m
   compute_engine_instance:
@@ -16,10 +15,15 @@ linux_x86_task:
     platform: linux
     cpu: 8
     memory: 8G
-
+  env:
+    VENV_ROOT: ${HOME}/venv-cibuildwheel
+    PATH: ${VENV_ROOT}/bin:${PATH}
   install_pre_requirements_script:
     - docker run --rm --privileged docker.io/tonistiigi/binfmt:latest --install all
-    - apt install -y python3-venv python-is-python3
+    - add-apt-repository -y ppa:deadsnakes/ppa
+    - apt-get update
+    - apt-get install -y python3.12-venv
+    - python3.12 -m venv ${VENV_ROOT}
   <<: *RUN_TESTS
 
 linux_aarch64_task:
@@ -30,10 +34,15 @@ linux_aarch64_task:
     platform: linux
     cpu: 4
     memory: 4G
-
+  env:
+    VENV_ROOT: ${HOME}/venv-cibuildwheel
+    PATH: ${VENV_ROOT}/bin:${PATH}
   install_pre_requirements_script:
     - docker run --rm --privileged docker.io/tonistiigi/binfmt:latest --install all
-    - apt install -y python3-venv python-is-python3
+    - add-apt-repository -y ppa:deadsnakes/ppa
+    - apt-get update
+    - apt-get install -y python3.12-venv
+    - python3.12 -m venv ${VENV_ROOT}
   <<: *RUN_TESTS
 
 windows_x86_task:
@@ -46,7 +55,7 @@ windows_x86_task:
     memory: 8G
 
   install_pre_requirements_script:
-    - choco install -y --no-progress python3 --version 3.10.6
+    - choco install -y --no-progress python3 --version 3.12.4
     - refreshenv
     - echo PATH=%PATH% >> "%CIRRUS_ENV%"
   <<: *RUN_TESTS
@@ -54,22 +63,24 @@ windows_x86_task:
 macos_arm64_task:
   macos_instance:
     image: ghcr.io/cirruslabs/macos-runner:sonoma
-
   env:
-    PATH: /opt/homebrew/opt/python@3.10/libexec/bin:$PATH
+    VENV_ROOT: ${HOME}/venv-cibuildwheel
+    PATH: ${VENV_ROOT}/bin:${PATH}
   install_pre_requirements_script:
-    - brew install python@3.10
+    - brew install python@3.12
+    - python3.12 -m venv ${VENV_ROOT}
   <<: *RUN_TESTS
 
 macos_arm64_cp38_task:
   macos_instance:
     image: ghcr.io/cirruslabs/macos-runner:sonoma
-
   env:
-    PATH: /opt/homebrew/opt/python@3.10/libexec/bin:$PATH
+    VENV_ROOT: ${HOME}/venv-cibuildwheel
+    PATH: ${VENV_ROOT}/bin:${PATH}
     PYTEST_ADDOPTS: --run-cp38-universal2 -k 'test_cp38_arm64_testing_universal2_installer or test_arch_auto'
   install_pre_requirements_script:
-    - brew install python@3.10
+    - brew install python@3.12
+    - python3.12 -m venv ${VENV_ROOT}
     - curl -fsSLO https://www.python.org/ftp/python/3.8.10/python-3.8.10-macos11.pkg
     - sudo installer -pkg python-3.8.10-macos11.pkg -target /
     - rm python-3.8.10-macos11.pkg
diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 40c2a8657..2b1c71a48 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -41,7 +41,7 @@ jobs:
         python_version: ['3.13']
         include:
         - os: ubuntu-latest
-          python_version: '3.8'
+          python_version: '3.11'
     timeout-minutes: 180
     steps:
     - uses: actions/checkout@v4
@@ -81,8 +81,7 @@ jobs:
       env:
         CIBW_ARCHS_MACOS: x86_64 universal2 arm64
         CIBW_BUILD_FRONTEND: 'build[uv]'
-        CIBW_FREE_THREADED_SUPPORT: 1
-        CIBW_PRERELEASE_PYTHONS: 1
+        CIBW_ENABLE: "cpython-prerelease cpython-freethreading pypy"
 
     - name: Run a sample build (GitHub Action, only)
       uses: ./
diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index befd44f0b..ef5c7e724 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -24,9 +24,9 @@ repos:
   rev: v1.14.0
   hooks:
   - id: mypy
-    name: mypy 3.8 on cibuildwheel/
+    name: mypy 3.11 on cibuildwheel/
     exclude: ^cibuildwheel/resources/.*py|bin/generate_schema.py$
-    args: ["--python-version=3.8"]
+    args: ["--python-version=3.11"]
     additional_dependencies: &mypy-dependencies
       - bracex
       - dependency-groups>=1.2
@@ -47,9 +47,9 @@ repos:
       - uv
       - validate-pyproject
   - id: mypy
-    name: mypy 3.12
+    name: mypy 3.13
     exclude: ^cibuildwheel/resources/.*py$
-    args: ["--python-version=3.12"]
+    args: ["--python-version=3.13"]
     additional_dependencies: *mypy-dependencies
 
 - repo: https://github.com/shellcheck-py/shellcheck-py
diff --git a/.travis.yml b/.travis.yml
index b610edf00..808459794 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -8,13 +8,13 @@ branches:
 
 jobs:
   include:
-    - name: Linux | x86_64 + i686 | Python 3.9
-      python: 3.9
+    - name: Linux | x86_64 + i686 | Python 3.11
+      python: 3.11
       services: docker
       env: PYTHON=python
 
-    - name: Linux | arm64 | Python 3.9
-      python: 3.9
+    - name: Linux | arm64 | Python 3.11
+      python: 3.11
       services: docker
       arch: arm64-graviton2
       group: edge
@@ -29,8 +29,8 @@ jobs:
           packages:
             - docker-ce docker-ce-cli containerd.io
 
-    - name: Linux | ppc64le | Python 3.9
-      python: 3.9
+    - name: Linux | ppc64le | Python 3.11
+      python: 3.11
       services: docker
       arch: ppc64le
       allow_failure: True
@@ -40,16 +40,16 @@ jobs:
         # c.f. https://travis-ci.community/t/running-out-of-disk-space-quota-when-using-docker-on-ppc64le/11634
         - PYTEST_ADDOPTS='-k "not test_manylinuxXXXX_only"'
 
-    - name: Windows | x86_64 | Python 3.9
+    - name: Windows | x86_64 | Python 3.11
       os: windows
       language: shell
       before_install:
-        - choco upgrade python3 -y --version 3.9.13 --limit-output --params "/InstallDir:C:\\Python39"
+        - choco upgrade python3 -y --version 3.11.9 --limit-output --params "/InstallDir:C:\\Python311"
       env:
-        - PYTHON=C:\\Python39\\python
+        - PYTHON=C:\\Python311\\python
 
-    - name: Linux | s390x | Python 3.9
-      python: 3.9
+    - name: Linux | s390x | Python 3.11
+      python: 3.11
       services: docker
       arch: s390x
       allow_failure: True
diff --git a/CI.md b/CI.md
index 25b001bf9..15de33c53 100644
--- a/CI.md
+++ b/CI.md
@@ -1,11 +1,11 @@
 This is a summary of the host Python versions and platforms covered by the different CI platforms:
 
-|         | 3.8                              | 3.9       | 3.10      | 3.11    | 3.12                                             |
-|---------|----------------------------------|-----------|-----------|---------|--------------------------------------------------|
-| Linux   | Azure Pipelines / GitHub Actions | Travis CI | Cirrus CI |         | AppVeyor¹ / CircleCI¹ / GitHub Actions / GitLab¹ |
-| macOS   | Azure Pipelines                  |           | Cirrus CI | GitLab¹ | AppVeyor¹ /CircleCI¹ / GitHub Actions            |
-| Windows | Azure Pipelines                  | Travis CI | Cirrus CI |         | AppVeyor¹ / GitHub Actions / GitLab¹             |
+|         | 3.11                                         | 3.12                                        | 3.13           |
+|---------|----------------------------------------------|---------------------------------------------|----------------|
+| Linux   | Azure Pipelines / GitHub Actions / Travis CI | AppVeyor¹ / CircleCI¹ / Cirrus CI / GitLab¹ | GitHub Actions |
+| macOS   | Azure Pipelines / GitLab¹                    | AppVeyor¹ / CircleCI¹ / Cirrus CI / GitLab¹ | GitHub Actions |
+| Windows | Azure Pipelines / Travis CI                  | AppVeyor¹ / Cirrus CI / GitLab¹             | GitHub Actions |
 
 > ¹ Runs a reduced set of tests to reduce CI load
 
-Non-x86 architectures are covered on Travis CI using Python 3.9.
+Non-x86 architectures are covered on Travis CI using Python 3.11.
diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index 6541244ca..76b1c6186 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -5,37 +5,37 @@ pr:
       - .pre-commit-config.yaml
 
 jobs:
-- job: linux_38
+- job: linux_311
   timeoutInMinutes: 120
   pool: {vmImage: 'Ubuntu-20.04'}
   steps:
     - task: UsePythonVersion@0
       inputs:
-        versionSpec: '3.8'
+        versionSpec: '3.11'
     - bash: |
         docker run --rm --privileged docker.io/tonistiigi/binfmt:latest --install all
         python -m pip install dependency-groups
         python -m dependency_groups test | xargs python -m pip install -e.
         python ./bin/run_tests.py
 
-- job: macos_38
+- job: macos_311
   pool: {vmImage: 'macOS-13'}
   steps:
     - task: UsePythonVersion@0
       inputs:
-        versionSpec: '3.8'
+        versionSpec: '3.11'
     - bash: |
         python -m pip install dependency-groups
         python -m dependency_groups test | xargs python -m pip install -e.
         python ./bin/run_tests.py --num-processes 2
 
-- job: windows_38
+- job: windows_311
   pool: {vmImage: 'windows-2019'}
   timeoutInMinutes: 180
   steps:
     - task: UsePythonVersion@0
       inputs:
-        versionSpec: '3.8'
+        versionSpec: '3.11'
     - bash: |
         python -m pip install dependency-groups
         python -m dependency_groups test | xargs python -m pip install -e.
diff --git a/bin/bump_version.py b/bin/bump_version.py
index e28bdcb97..2c56caff7 100755
--- a/bin/bump_version.py
+++ b/bin/bump_version.py
@@ -11,17 +11,13 @@
 import os
 import subprocess
 import sys
+import tomllib
 import urllib.parse
 from pathlib import Path
 
 import click
 from packaging.version import InvalidVersion, Version
 
-if sys.version_info < (3, 11):
-    import tomli as tomllib
-else:
-    import tomllib
-
 config = [
     # file path, version find/replace format
     ("pyproject.toml", 'version = "{}"'),
diff --git a/bin/generate_schema.py b/bin/generate_schema.py
index 0ef4f0125..e4a39e3b0 100755
--- a/bin/generate_schema.py
+++ b/bin/generate_schema.py
@@ -119,11 +119,6 @@
     description: Set environment variables on the host to pass-through to the container
       during the build.
     type: string_array
-  free-threaded-support:
-    type: boolean
-    default: false
-    description: The project supports free-threaded builds of Python (PEP703)
-    deprecated: Use the `enable` option instead.
   manylinux-aarch64-image:
     type: string
     description: Specify alternative manylinux / musllinux container images
@@ -277,7 +272,6 @@
 del non_global_options["build"]
 del non_global_options["skip"]
 del non_global_options["test-skip"]
-del non_global_options["free-threaded-support"]
 del non_global_options["enable"]
 
 overrides["items"]["properties"]["select"]["oneOf"] = string_array
diff --git a/bin/update_nodejs.py b/bin/update_nodejs.py
index c2cb1c0f0..8a08274ae 100755
--- a/bin/update_nodejs.py
+++ b/bin/update_nodejs.py
@@ -4,6 +4,7 @@
 
 import difflib
 import logging
+import tomllib
 from dataclasses import dataclass
 from pathlib import Path
 from typing import Final
@@ -16,8 +17,6 @@
 from rich.logging import RichHandler
 from rich.syntax import Syntax
 
-from cibuildwheel._compat import tomllib
-
 log = logging.getLogger("cibw")
 
 # Looking up the dir instead of using utils.resources_dir
diff --git a/bin/update_pythons.py b/bin/update_pythons.py
index ecf8e3ef2..5921b427b 100755
--- a/bin/update_pythons.py
+++ b/bin/update_pythons.py
@@ -5,9 +5,10 @@
 import copy
 import difflib
 import logging
+import tomllib
 from collections.abc import Mapping, MutableMapping
 from pathlib import Path
-from typing import Any, Final, Literal, TypedDict, Union
+from typing import Any, Final, Literal, TypedDict
 
 import click
 import requests
@@ -17,7 +18,6 @@
 from rich.logging import RichHandler
 from rich.syntax import Syntax
 
-from cibuildwheel._compat import tomllib
 from cibuildwheel.extra import dump_python_configurations
 
 log = logging.getLogger("cibw")
@@ -50,7 +50,7 @@ class ConfigMacOS(TypedDict):
     url: str
 
 
-AnyConfig = Union[ConfigWinCP, ConfigWinPP, ConfigMacOS]
+AnyConfig = ConfigWinCP | ConfigWinPP | ConfigMacOS
 
 
 # The following set of "Versions" classes allow the initial call to the APIs to
diff --git a/bin/update_virtualenv.py b/bin/update_virtualenv.py
index b458c3f89..dffdb2561 100755
--- a/bin/update_virtualenv.py
+++ b/bin/update_virtualenv.py
@@ -5,6 +5,7 @@
 import difflib
 import logging
 import subprocess
+import tomllib
 from dataclasses import dataclass
 from pathlib import Path
 from typing import Final
@@ -15,8 +16,6 @@
 from rich.logging import RichHandler
 from rich.syntax import Syntax
 
-from cibuildwheel._compat import tomllib
-
 log = logging.getLogger("cibw")
 
 # Looking up the dir instead of using utils.resources_dir
diff --git a/cibuildwheel/__main__.py b/cibuildwheel/__main__.py
index ffdde57bf..691d88ed1 100644
--- a/cibuildwheel/__main__.py
+++ b/cibuildwheel/__main__.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
 import argparse
+import contextlib
 import dataclasses
 import os
 import shutil
@@ -12,7 +13,7 @@
 from collections.abc import Iterable, Sequence, Set
 from pathlib import Path
 from tempfile import mkdtemp
-from typing import Protocol
+from typing import Protocol, assert_never
 
 import cibuildwheel
 import cibuildwheel.linux
@@ -21,7 +22,6 @@
 import cibuildwheel.util
 import cibuildwheel.windows
 from cibuildwheel import errors
-from cibuildwheel._compat.typing import assert_never
 from cibuildwheel.architecture import Architecture, allowed_architectures_check
 from cibuildwheel.logger import log
 from cibuildwheel.options import CommandLineArguments, Options, compute_options
@@ -30,8 +30,8 @@
     CIBW_CACHE_PATH,
     BuildSelector,
     CIProvider,
+    EnableGroup,
     Unbuffered,
-    chdir,
     detect_ci_provider,
     fix_ansi_codes_for_github_actions,
     strtobool,
@@ -101,6 +101,17 @@ def main_inner(global_options: GlobalOptions) -> None:
         """,
     )
 
+    enable_groups_str = ", ".join(g.value for g in EnableGroup)
+    parser.add_argument(
+        "--enable",
+        action="append",
+        default=[],
+        metavar="GROUP",
+        help=f"""
+            Enable an additional category of builds. Use multiple times to select multiple groups. Choices: {enable_groups_str}.
+        """,
+    )
+
     parser.add_argument(
         "--only",
         default=None,
@@ -157,12 +168,6 @@ def main_inner(global_options: GlobalOptions) -> None:
         help="Do not report an error code if the build does not match any wheels.",
     )
 
-    parser.add_argument(
-        "--prerelease-pythons",
-        action="store_true",
-        help="Enable pre-release Python versions if available.",
-    )
-
     parser.add_argument(
         "--debug-traceback",
         action="store_true",
@@ -200,7 +205,7 @@ def main_inner(global_options: GlobalOptions) -> None:
         # This is now the new package dir
         args.package_dir = project_dir.resolve()
 
-        with chdir(project_dir):
+        with contextlib.chdir(project_dir):
             build_in_directory(args)
     finally:
         # avoid https://github.com/python/cpython/issues/86962 by performing
@@ -418,10 +423,10 @@ def detect_warnings(*, options: Options, identifiers: Iterable[str]) -> list[str
         if any(o and ("{python}" in o or "{pip}" in o) for o in option_values):
             # Reminder: in an f-string, double braces means literal single brace
             msg = (
-                f"{option_name}: '{{python}}' and '{{pip}}' are no longer needed, "
-                "and will be removed in cibuildwheel 3. Simply use 'python' or 'pip' instead."
+                f"{option_name}: '{{python}}' and '{{pip}}' are no longer supported "
+                "and have been removed in cibuildwheel 3. Simply use 'python' or 'pip' instead."
             )
-            warnings.append(msg)
+            raise errors.ConfigurationError(msg)
 
     return warnings
 
diff --git a/cibuildwheel/_compat/__init__.py b/cibuildwheel/_compat/__init__.py
deleted file mode 100644
index 9d48db4f9..000000000
--- a/cibuildwheel/_compat/__init__.py
+++ /dev/null
@@ -1 +0,0 @@
-from __future__ import annotations
diff --git a/cibuildwheel/_compat/tomllib.py b/cibuildwheel/_compat/tomllib.py
deleted file mode 100644
index b061ba911..000000000
--- a/cibuildwheel/_compat/tomllib.py
+++ /dev/null
@@ -1,10 +0,0 @@
-from __future__ import annotations
-
-import sys
-
-if sys.version_info >= (3, 11):
-    from tomllib import load, loads
-else:
-    from tomli import load, loads
-
-__all__ = ["load", "loads"]
diff --git a/cibuildwheel/_compat/typing.py b/cibuildwheel/_compat/typing.py
deleted file mode 100644
index eb11302ab..000000000
--- a/cibuildwheel/_compat/typing.py
+++ /dev/null
@@ -1,14 +0,0 @@
-from __future__ import annotations
-
-import sys
-
-if sys.version_info < (3, 11):
-    from typing_extensions import NotRequired, Self, assert_never
-else:
-    from typing import NotRequired, Self, assert_never
-
-__all__ = (
-    "NotRequired",
-    "Self",
-    "assert_never",
-)
diff --git a/cibuildwheel/architecture.py b/cibuildwheel/architecture.py
index 0f622def9..444d37017 100644
--- a/cibuildwheel/architecture.py
+++ b/cibuildwheel/architecture.py
@@ -6,9 +6,8 @@
 import sys
 from collections.abc import Set
 from enum import Enum
-from typing import Final, Literal
+from typing import Final, Literal, assert_never
 
-from ._compat.typing import assert_never
 from .typing import PlatformName
 
 PRETTY_NAMES: Final[dict[PlatformName, str]] = {
diff --git a/cibuildwheel/bashlex_eval.py b/cibuildwheel/bashlex_eval.py
index c5f805372..749665394 100644
--- a/cibuildwheel/bashlex_eval.py
+++ b/cibuildwheel/bashlex_eval.py
@@ -1,14 +1,18 @@
 from __future__ import annotations
 
 import subprocess
-from collections.abc import Iterable, Mapping, Sequence
+from collections.abc import (
+    Callable,
+    Iterable,
+    Mapping,
+    Sequence,
+)
 from dataclasses import dataclass
-from typing import Callable, Dict, List  # noqa: TID251
 
 import bashlex
 
 # a function that takes a command and the environment, and returns the result
-EnvironmentExecutor = Callable[[List[str], Dict[str, str]], str]
+EnvironmentExecutor = Callable[[list[str], dict[str, str]], str]
 
 
 def local_environment_executor(command: Sequence[str], env: Mapping[str, str]) -> str:
diff --git a/cibuildwheel/linux.py b/cibuildwheel/linux.py
index 1ffe96f9a..d4bac7bb5 100644
--- a/cibuildwheel/linux.py
+++ b/cibuildwheel/linux.py
@@ -4,15 +4,15 @@
 import subprocess
 import sys
 import textwrap
+from collections import OrderedDict
 from collections.abc import Iterable, Iterator, Sequence, Set
 from dataclasses import dataclass
 from pathlib import Path, PurePath, PurePosixPath
-from typing import OrderedDict, Tuple
+from typing import assert_never
 
 from packaging.version import Version
 
 from . import errors
-from ._compat.typing import assert_never
 from .architecture import Architecture
 from .logger import log
 from .oci_container import OCIContainer, OCIContainerEngineConfig, OCIPlatform
@@ -104,7 +104,7 @@ def get_build_steps(
     Groups PythonConfigurations into BuildSteps. Each BuildStep represents a
     separate container instance.
     """
-    steps = OrderedDict[Tuple[str, str, str, OCIContainerEngineConfig], BuildStep]()
+    steps = OrderedDict[tuple[str, str, str, OCIContainerEngineConfig], BuildStep]()
 
     for config in python_configurations:
         _, platform_tag = config.identifier.split("-", 1)
diff --git a/cibuildwheel/logger.py b/cibuildwheel/logger.py
index 542576076..b88093814 100644
--- a/cibuildwheel/logger.py
+++ b/cibuildwheel/logger.py
@@ -5,11 +5,11 @@
 import re
 import sys
 import time
-from typing import IO, AnyStr, Final, Tuple
+from typing import IO, AnyStr, Final
 
 from .util import CIProvider, detect_ci_provider
 
-FoldPattern = Tuple[str, str]
+FoldPattern = tuple[str, str]
 DEFAULT_FOLD_PATTERN: Final[FoldPattern] = ("{name}", "")
 FOLD_PATTERNS: Final[dict[str, FoldPattern]] = {
     "azure": ("##[group]{name}", "##[endgroup]"),
diff --git a/cibuildwheel/macos.py b/cibuildwheel/macos.py
index fcc88dac9..bea0a25d8 100644
--- a/cibuildwheel/macos.py
+++ b/cibuildwheel/macos.py
@@ -12,13 +12,12 @@
 from collections.abc import Sequence, Set
 from dataclasses import dataclass
 from pathlib import Path
-from typing import Literal, Tuple
+from typing import Literal, assert_never
 
 from filelock import FileLock
 from packaging.version import Version
 
 from . import errors
-from ._compat.typing import assert_never
 from .architecture import Architecture
 from .environment import ParsedEnvironment
 from .logger import log
@@ -50,7 +49,7 @@
 )
 
 
-@functools.lru_cache(maxsize=None)
+@functools.cache
 def get_macos_version() -> tuple[int, int]:
     """
     Returns the macOS major/minor version, as a tuple, e.g. (10, 15) or (11, 0)
@@ -74,10 +73,10 @@ def get_macos_version() -> tuple[int, int]:
             capture_stdout=True,
         )
         version = tuple(map(int, version_str.split(".")[:2]))
-    return typing.cast(Tuple[int, int], version)
+    return typing.cast(tuple[int, int], version)
 
 
-@functools.lru_cache(maxsize=None)
+@functools.cache
 def get_test_macosx_deployment_target() -> str:
     version = get_macos_version()
     if version >= (11, 0):
diff --git a/cibuildwheel/oci_container.py b/cibuildwheel/oci_container.py
index 646bbc643..3e4e6ada5 100644
--- a/cibuildwheel/oci_container.py
+++ b/cibuildwheel/oci_container.py
@@ -16,9 +16,8 @@
 from enum import Enum
 from pathlib import Path, PurePath, PurePosixPath
 from types import TracebackType
-from typing import IO, Dict, Literal
+from typing import IO, Literal, Self, assert_never
 
-from ._compat.typing import Self, assert_never
 from .errors import OCIEngineTooOldError
 from .logger import log
 from .typing import PathOrStr, PopenBytes
@@ -489,7 +488,7 @@ def get_environment(self) -> dict[str, str]:
                 capture_output=True,
             )
         )
-        return typing.cast(Dict[str, str], env)
+        return typing.cast(dict[str, str], env)
 
     def environment_executor(self, command: Sequence[str], environment: dict[str, str]) -> str:
         # used as an EnvironmentExecutor to evaluate commands and capture output
diff --git a/cibuildwheel/options.py b/cibuildwheel/options.py
index 3fb9ebb73..3ab736e90 100644
--- a/cibuildwheel/options.py
+++ b/cibuildwheel/options.py
@@ -9,15 +9,14 @@
 import functools
 import shlex
 import textwrap
-from collections.abc import Generator, Iterable, Set
+import tomllib
+from collections.abc import Generator, Iterable, Mapping, Sequence, Set
 from pathlib import Path
-from typing import Any, Literal, Mapping, Sequence, Union  # noqa: TID251
+from typing import Any, Literal, assert_never
 
 from packaging.specifiers import SpecifierSet
 
 from . import errors
-from ._compat import tomllib
-from ._compat.typing import assert_never
 from .architecture import Architecture
 from .environment import EnvironmentParseError, ParsedEnvironment, parse_environment
 from .logger import log
@@ -30,10 +29,9 @@
     BuildFrontendConfig,
     BuildSelector,
     DependencyConstraints,
-    EnableGroups,
+    EnableGroup,
     TestSelector,
     format_safe,
-    read_python_configs,
     resources_dir,
     selector_matches,
     strtobool,
@@ -51,8 +49,8 @@ class CommandLineArguments:
     package_dir: Path
     print_build_identifiers: bool
     allow_empty: bool
-    prerelease_pythons: bool
     debug_traceback: bool
+    enable: list[str]
 
     @staticmethod
     def defaults() -> CommandLineArguments:
@@ -64,9 +62,9 @@ def defaults() -> CommandLineArguments:
             config_file="",
             output_dir=Path("wheelhouse"),
             package_dir=Path("."),
-            prerelease_pythons=False,
             print_build_identifiers=False,
             debug_traceback=False,
+            enable=[],
         )
 
 
@@ -121,10 +119,10 @@ def architectures(self) -> set[Architecture]:
         return self.globals.architectures
 
 
-SettingLeaf = Union[str, int, bool]
+SettingLeaf = str | int | bool
 SettingList = Sequence[SettingLeaf]
-SettingTable = Mapping[str, Union[SettingLeaf, SettingList]]
-SettingValue = Union[SettingTable, SettingList, SettingLeaf]
+SettingTable = Mapping[str, SettingLeaf | SettingList]
+SettingValue = SettingTable | SettingList | SettingLeaf
 
 
 @dataclasses.dataclass(frozen=True)
@@ -359,7 +357,7 @@ def _stringify_setting(
             msg = f"Error converting {setting!r} to a string: this setting doesn't accept a list"
             raise OptionsReaderError(msg) from None
 
-    if isinstance(setting, (bool, int)):
+    if isinstance(setting, bool | int):
         return str(setting)
 
     return setting
@@ -617,28 +615,13 @@ def globals(self) -> GlobalOptions:
         enable_groups = self.reader.get(
             "enable", env_plat=False, option_format=ListFormat(sep=" "), env_rule=InheritRule.APPEND
         )
-        enable = {EnableGroups(group) for group in enable_groups.split()}
-
-        free_threaded_support = strtobool(
-            self.reader.get("free-threaded-support", env_plat=False, ignore_empty=True)
-        )
-
-        prerelease_pythons = args.prerelease_pythons or strtobool(
-            self.env.get("CIBW_PRERELEASE_PYTHONS", "0")
-        )
-
-        if free_threaded_support or prerelease_pythons:
-            msg = (
-                "free-threaded-support and prerelease-pythons should be specified by enable instead"
-            )
-            if enable:
-                raise OptionsReaderError(msg)
-            log.warning(msg)
-
-        if free_threaded_support:
-            enable.add(EnableGroups.CPythonFreeThreading)
-        if prerelease_pythons:
-            enable.add(EnableGroups.CPythonPrerelease)
+        try:
+            enable = {EnableGroup(group) for group in enable_groups.split()}
+            for command_line_group in args.enable:
+                enable.add(EnableGroup(command_line_group))
+        except ValueError as e:
+            msg = f"Failed to parse enable group. {e}. Valid group names are: {', '.join(g.value for g in EnableGroup)}"
+            raise errors.ConfigurationError(msg) from e
 
         # 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
@@ -655,30 +638,16 @@ def globals(self) -> GlobalOptions:
             build_config = args.only
             skip_config = ""
             architectures = Architecture.all_archs(self.platform)
-            enable = set(EnableGroups)
+            enable = set(EnableGroup)
 
         build_selector = BuildSelector(
             build_config=build_config,
             skip_config=skip_config,
             requires_python=requires_python,
-            enable=frozenset(
-                enable | {EnableGroups.PyPy}
-            ),  # For backwards compatibility, we are adding PyPy for now
+            enable=frozenset(enable),
         )
         test_selector = TestSelector(skip_config=test_skip)
 
-        all_configs = read_python_configs(self.platform)
-        all_pypy_ids = {
-            config["identifier"] for config in all_configs if config["identifier"].startswith("pp")
-        }
-        if (
-            not self._defaults
-            and EnableGroups.PyPy not in enable
-            and any(build_selector(build_id) for build_id in all_pypy_ids)
-        ):
-            msg = "PyPy builds will be disabled by default in version 3. Enabling PyPy builds should be specified by enable"
-            log.warning(msg)
-
         return GlobalOptions(
             package_dir=package_dir,
             output_dir=output_dir,
@@ -976,7 +945,7 @@ def compute_options(
     return options
 
 
-@functools.lru_cache(maxsize=None)
+@functools.cache
 def _get_pinned_container_images() -> Mapping[str, Mapping[str, str]]:
     """
     This looks like a dict of dicts, e.g.
diff --git a/cibuildwheel/resources/cibuildwheel.schema.json b/cibuildwheel/resources/cibuildwheel.schema.json
index e9ef3985b..5f432dc42 100644
--- a/cibuildwheel/resources/cibuildwheel.schema.json
+++ b/cibuildwheel/resources/cibuildwheel.schema.json
@@ -284,13 +284,6 @@
       ],
       "title": "CIBW_ENVIRONMENT_PASS"
     },
-    "free-threaded-support": {
-      "type": "boolean",
-      "default": false,
-      "description": "The project supports free-threaded builds of Python (PEP703)",
-      "deprecated": "Use the `enable` option instead.",
-      "title": "CIBW_FREE_THREADED_SUPPORT"
-    },
     "manylinux-aarch64-image": {
       "type": "string",
       "description": "Specify alternative manylinux / musllinux container images",
diff --git a/cibuildwheel/resources/defaults.toml b/cibuildwheel/resources/defaults.toml
index 3c56dfc58..27fd8214d 100644
--- a/cibuildwheel/resources/defaults.toml
+++ b/cibuildwheel/resources/defaults.toml
@@ -2,7 +2,6 @@
 build = "*"
 skip = ""
 test-skip = ""
-free-threaded-support = false
 enable = []
 
 archs = ["auto"]
diff --git a/cibuildwheel/typing.py b/cibuildwheel/typing.py
index 367cfcdf1..34ae273c8 100644
--- a/cibuildwheel/typing.py
+++ b/cibuildwheel/typing.py
@@ -15,7 +15,7 @@
 
 if typing.TYPE_CHECKING:
     PopenBytes = subprocess.Popen[bytes]
-    PathOrStr = Union[str, os.PathLike[str]]
+    PathOrStr = str | os.PathLike[str]
 else:
     PopenBytes = subprocess.Popen
     PathOrStr = Union[str, "os.PathLike[str]"]
diff --git a/cibuildwheel/util.py b/cibuildwheel/util.py
index 905dd5410..abae60db4 100644
--- a/cibuildwheel/util.py
+++ b/cibuildwheel/util.py
@@ -14,13 +14,14 @@
 import tarfile
 import textwrap
 import time
+import tomllib
 import typing
 import urllib.request
 from collections import defaultdict
 from collections.abc import Generator, Iterable, Mapping, MutableMapping, Sequence
 from dataclasses import dataclass
 from enum import Enum
-from functools import lru_cache, total_ordering
+from functools import cache, total_ordering
 from pathlib import Path, PurePath
 from tempfile import TemporaryDirectory
 from time import sleep
@@ -36,16 +37,14 @@
 from packaging.version import Version
 from platformdirs import user_cache_path
 
-from ._compat import tomllib
 from .architecture import Architecture
 from .errors import FatalError
 from .typing import PathOrStr, PlatformName
 
 __all__ = [
     "MANYLINUX_ARCHS",
-    "EnableGroups",
+    "EnableGroup",
     "call",
-    "chdir",
     "combine_constraints",
     "find_compatible_wheel",
     "find_uv",
@@ -69,7 +68,7 @@
 test_fail_cwd_file: Final[Path] = resources_dir / "testing_temp_dir_file.py"
 
 
-class EnableGroups(enum.Enum):
+class EnableGroup(enum.Enum):
     """
     Groups of build selectors that are not enabled by default.
     """
@@ -220,12 +219,12 @@ def format_safe(template: str, **kwargs: str | os.PathLike[str]) -> str:
 
 def prepare_command(command: str, **kwargs: PathOrStr) -> str:
     """
-    Preprocesses a command by expanding variables like {python}.
+    Preprocesses a command by expanding variables like {project}.
 
     For example, used in the test_command option to specify the path to the
     project's root. Unmatched syntax will mostly be allowed through.
     """
-    return format_safe(command, python="python", pip="pip", **kwargs)
+    return format_safe(command, **kwargs)
 
 
 def get_build_verbosity_extra_flags(level: int) -> list[str]:
@@ -280,7 +279,7 @@ class BuildSelector:
     build_config: str
     skip_config: str
     requires_python: SpecifierSet | None = None
-    enable: frozenset[EnableGroups] = frozenset()
+    enable: frozenset[EnableGroup] = frozenset()
 
     def __call__(self, build_id: str) -> bool:
         # Filter build selectors by python_requires if set
@@ -295,15 +294,15 @@ def __call__(self, build_id: str) -> bool:
                 return False
 
         # filter out groups that are not enabled
-        if EnableGroups.CPythonFreeThreading not in self.enable and selector_matches(
+        if EnableGroup.CPythonFreeThreading not in self.enable and selector_matches(
             "cp3??t-*", build_id
         ):
             return False
-        if EnableGroups.CPythonPrerelease not in self.enable and selector_matches(
+        if EnableGroup.CPythonPrerelease not in self.enable and selector_matches(
             "cp314*", build_id
         ):
             return False
-        if EnableGroups.PyPy not in self.enable and selector_matches("pp*", build_id):
+        if EnableGroup.PyPy not in self.enable and selector_matches("pp*", build_id):
             return False
 
         should_build = selector_matches(self.build_config, build_id)
@@ -596,7 +595,7 @@ def get_pip_version(env: Mapping[str, str]) -> str:
     return pip_version
 
 
-@lru_cache(maxsize=None)
+@cache
 def ensure_node(major_version: str) -> Path:
     input_file = resources_dir / "nodejs.toml"
     with input_file.open("rb") as f:
@@ -628,7 +627,7 @@ def ensure_node(major_version: str) -> Path:
     return path
 
 
-@lru_cache(maxsize=None)
+@cache
 def _ensure_virtualenv(version: str) -> Path:
     version_parts = version.split(".")
     key = f"py{version_parts[0]}{version_parts[1]}"
@@ -804,19 +803,6 @@ def find_compatible_wheel(wheels: Sequence[T], identifier: str) -> T | None:
     return None
 
 
-# Can be replaced by contextlib.chdir in Python 3.11
-@contextlib.contextmanager
-def chdir(new_path: Path | str) -> Generator[None, None, None]:
-    """Non thread-safe context manager to change the current working directory."""
-
-    cwd = os.getcwd()
-    try:
-        os.chdir(new_path)
-        yield
-    finally:
-        os.chdir(cwd)
-
-
 def fix_ansi_codes_for_github_actions(text: str) -> str:
     """
     Github Actions forgets the current ANSI style on every new line. This
diff --git a/cibuildwheel/windows.py b/cibuildwheel/windows.py
index 8f5633d67..c88430dee 100644
--- a/cibuildwheel/windows.py
+++ b/cibuildwheel/windows.py
@@ -7,14 +7,14 @@
 import textwrap
 from collections.abc import MutableMapping, Sequence, Set
 from dataclasses import dataclass
-from functools import lru_cache
+from functools import cache
 from pathlib import Path
+from typing import assert_never
 
 from filelock import FileLock
 from packaging.version import Version
 
 from . import errors
-from ._compat.typing import assert_never
 from .architecture import Architecture
 from .environment import ParsedEnvironment
 from .logger import log
@@ -96,7 +96,7 @@ def get_python_configurations(
     return python_configurations
 
 
-@lru_cache(maxsize=None)
+@cache
 def _ensure_nuget() -> Path:
     nuget = CIBW_CACHE_PATH / "nuget.exe"
     with FileLock(str(nuget) + ".lock"):
diff --git a/docs/options.md b/docs/options.md
index a1452e17a..ad8fee6fb 100644
--- a/docs/options.md
+++ b/docs/options.md
@@ -567,17 +567,14 @@ values are:
 
 
 - `cpython-prerelease`: Enables beta versions of Pythons if any are available
-  (May-July, approximately). For backward compatibility, `CIBW_PRERELEASE_PYTHONS`
-  is also supported until cibuildwheel 3.
+  (May-July, approximately).
 - `cpython-freethreading`: [PEP 703](https://www.python.org/dev/peps/pep-0703)
   introduced variants of CPython that can be built without the Global
   Interpreter Lock (GIL).  Those variants are also known as free-threaded /
   no-gil. This will enable building these wheels while they are experimental.
   The build identifiers for those variants have a `t` suffix in their
-  `python_tag` (e.g. `cp313t-manylinux_x86_64`).  For backward compatibility,
-  `CIBW_FREE_THREADED_SUPPORT` is also supported until cibuildwheel 3.
-- `pypy`: Enable PyPy. For backward compatibility, this is always enabled until
-  cibuildwheel 3 is released.
+  `python_tag` (e.g. `cp313t-manylinux_x86_64`).
+- `pypy`: Enable PyPy.
 
 
 !!! caution
@@ -591,7 +588,7 @@ values are:
 !!! note
     Free threading is experimental: [What’s New In Python 3.13](https://docs.python.org/3.13/whatsnew/3.13.html#free-threaded-cpython)
 
-Default: empty (`pypy` is always injected).
+Default: empty.
 
 This option doesn't support overrides or platform specific variants; it is
 intended as a way to acknowledge that a project is aware that these extra
diff --git a/pyproject.toml b/pyproject.toml
index 3b0d72d1f..42b903fb9 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -8,7 +8,7 @@ version = "2.22.0"
 description = "Build Python wheels on CI with minimal configuration."
 readme = "README.md"
 license = "BSD-2-Clause"
-requires-python = ">=3.8"
+requires-python = ">=3.11"
 authors = [
     { name = "Joe Rickerby", email = "joerick@mac.com" },
 ]
@@ -30,9 +30,6 @@ classifiers = [
     "Natural Language :: English",
     "Programming Language :: Python :: 3",
     "Programming Language :: Python :: 3 :: Only",
-    "Programming Language :: Python :: 3.8",
-    "Programming Language :: Python :: 3.9",
-    "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",
     "Programming Language :: Python :: 3.13",
@@ -46,9 +43,7 @@ dependencies = [
     "dependency-groups>=1.2",
     "filelock",
     "packaging>=20.9",
-    "platformdirs",
-    "tomli;python_version < '3.11'",
-    "typing-extensions>=4.1.0;python_version < '3.11'",
+    "platformdirs"
 ]
 
 [project.optional-dependencies]
@@ -109,7 +104,7 @@ log_cli_level = "info"
 
 
 [tool.mypy]
-python_version = "3.8"
+python_version = "3.11"
 files = [
     "cibuildwheel/*.py",
     "test/**/*.py",
@@ -141,7 +136,7 @@ ignore_missing_imports = true
 
 
 [tool.pylint]
-py-version = "3.8"
+py-version = "3.11"
 jobs = "0"
 fail-on = ["E", "F"]
 fail-under = "9.8"
@@ -211,7 +206,6 @@ ignore = [
   "PYI025", # Set as AbstractSet
   "ISC001", # Conflicts with formatter
 ]
-typing-modules = ["cibuildwheel._compat.typing"]
 flake8-unused-arguments.ignore-variadic-names = true
 
 [tool.ruff.lint.flake8-tidy-imports.banned-api]
@@ -220,14 +214,9 @@ flake8-unused-arguments.ignore-variadic-names = true
 "typing.Iterator".msg = "Use collections.abc.Iterator instead."
 "typing.Sequence".msg = "Use collections.abc.Sequence instead."
 "typing.Set".msg = "Use collections.abc.Set instead."
-"typing.NotRequired".msg = "Use cibuildwheel._compat.typing.NotRequired instead."
-"typing.assert_never".msg = "Use cibuildwheel._compat.typing.assert_never instead."
-"tomllib".msg = "Use cibuildwheel._compat.tomllib instead."
-"tomli".msg = "Use cibuildwheel._compat.tomllib instead."
 
 [tool.ruff.lint.per-file-ignores]
 "unit_test/*" = ["PLC1901"]
-"cibuildwheel/_compat/**.py" = ["TID251"]
 "bin/*" = ["TID251"]
 
 [tool.repo-review]
diff --git a/test/conftest.py b/test/conftest.py
index a42a3ce9a..42a0d9acf 100644
--- a/test/conftest.py
+++ b/test/conftest.py
@@ -2,7 +2,7 @@
 
 import json
 import subprocess
-from typing import Generator
+from collections.abc import Generator
 
 import pytest
 
diff --git a/test/test_projects/base.py b/test/test_projects/base.py
index d7a9305a5..99ccc8b33 100644
--- a/test/test_projects/base.py
+++ b/test/test_projects/base.py
@@ -1,12 +1,12 @@
 from __future__ import annotations
 
 from pathlib import Path
-from typing import Any, Dict, Union
+from typing import Any
 
 import jinja2
 
-FilesDict = Dict[str, Union[str, jinja2.Template]]
-TemplateContext = Dict[str, Any]
+FilesDict = dict[str, str | jinja2.Template]
+TemplateContext = dict[str, Any]
 
 
 class TestProject:
diff --git a/test/utils.py b/test/utils.py
index aa23638d6..309a5649a 100644
--- a/test/utils.py
+++ b/test/utils.py
@@ -47,11 +47,11 @@ def cibuildwheel_get_build_identifiers(
     for the current platform.
     """
     cmd = [sys.executable, "-m", "cibuildwheel", "--print-build-identifiers", str(project_path)]
-    if prerelease_pythons:
-        cmd.append("--prerelease-pythons")
     if env is None:
         env = os.environ.copy()
-    env.setdefault("CIBW_FREE_THREADED_SUPPORT", "1")
+    env["CIBW_ENABLE"] = "cpython-freethreading pypy"
+    if prerelease_pythons:
+        env["CIBW_ENABLE"] += " cpython-prerelease"
 
     cmd_output = subprocess.run(
         cmd,
@@ -115,7 +115,7 @@ def cibuildwheel_run(
 
     _update_pip_cache_dir(env)
 
-    env.setdefault("CIBW_FREE_THREADED_SUPPORT", "1")
+    env["CIBW_ENABLE"] = "cpython-prerelease cpython-freethreading pypy"
 
     if single_python:
         env["CIBW_BUILD"] = "cp{}{}-*".format(*SINGLE_PYTHON_VERSION)
@@ -126,7 +126,6 @@ def cibuildwheel_run(
                 sys.executable,
                 "-m",
                 "cibuildwheel",
-                "--prerelease-pythons",
                 "--output-dir",
                 str(output_dir or tmp_output_dir),
                 str(package_dir),
diff --git a/unit_test/build_ids_test.py b/unit_test/build_ids_test.py
index a42af93de..0a444e85c 100644
--- a/unit_test/build_ids_test.py
+++ b/unit_test/build_ids_test.py
@@ -1,8 +1,9 @@
 from __future__ import annotations
 
+import tomllib
+
 from packaging.version import Version
 
-from cibuildwheel._compat import tomllib
 from cibuildwheel.extra import Printable, dump_python_configurations
 from cibuildwheel.util import resources_dir
 
diff --git a/unit_test/build_selector_test.py b/unit_test/build_selector_test.py
index 886202007..84359abba 100644
--- a/unit_test/build_selector_test.py
+++ b/unit_test/build_selector_test.py
@@ -2,12 +2,12 @@
 
 from packaging.specifiers import SpecifierSet
 
-from cibuildwheel.util import BuildSelector, EnableGroups
+from cibuildwheel.util import BuildSelector, EnableGroup
 
 
 def test_build():
     build_selector = BuildSelector(
-        build_config="cp3*-* *-manylinux*", skip_config="", enable=frozenset([EnableGroups.PyPy])
+        build_config="cp3*-* *-manylinux*", skip_config="", enable=frozenset([EnableGroup.PyPy])
     )
 
     assert build_selector("cp36-manylinux_x86_64")
@@ -45,7 +45,7 @@ def test_build_filter_pre():
     build_selector = BuildSelector(
         build_config="cp3*-* *-manylinux*",
         skip_config="",
-        enable=frozenset([EnableGroups.CPythonPrerelease, EnableGroups.PyPy]),
+        enable=frozenset([EnableGroup.CPythonPrerelease, EnableGroup.PyPy]),
     )
 
     assert build_selector("cp37-manylinux_x86_64")
@@ -59,7 +59,7 @@ def test_skip():
     build_selector = BuildSelector(
         build_config="*",
         skip_config="pp36-* cp3?-manylinux_i686 cp36-win* *-win32",
-        enable=frozenset([EnableGroups.PyPy]),
+        enable=frozenset([EnableGroup.PyPy]),
     )
 
     assert not build_selector("pp36-manylinux_x86_64")
@@ -85,7 +85,7 @@ def test_build_and_skip():
     build_selector = BuildSelector(
         build_config="cp36-* cp37-macosx* *-manylinux*",
         skip_config="pp37-* cp37-manylinux_i686",
-        enable=frozenset([EnableGroups.PyPy]),
+        enable=frozenset([EnableGroup.PyPy]),
     )
 
     assert not build_selector("pp37-manylinux_x86_64")
@@ -119,7 +119,7 @@ def test_build_limited_python():
         build_config="*",
         skip_config="",
         requires_python=SpecifierSet(">=3.7"),
-        enable=frozenset([EnableGroups.PyPy]),
+        enable=frozenset([EnableGroup.PyPy]),
     )
 
     assert not build_selector("cp36-manylinux_x86_64")
@@ -155,7 +155,7 @@ def test_build_limited_python_patch():
 
 
 def test_build_free_threaded_python():
-    build_selector = BuildSelector(build_config="*", skip_config="", enable=frozenset(EnableGroups))
+    build_selector = BuildSelector(build_config="*", skip_config="", enable=frozenset(EnableGroup))
 
     assert build_selector("cp313t-manylinux_x86_64")
 
diff --git a/unit_test/get_platform_test.py b/unit_test/get_platform_test.py
index dfcc7d87b..c9c312e50 100644
--- a/unit_test/get_platform_test.py
+++ b/unit_test/get_platform_test.py
@@ -1,7 +1,6 @@
 import contextlib
 import sys
 from pathlib import Path
-from typing import Dict
 
 import pytest
 import setuptools._distutils.util
@@ -16,7 +15,7 @@
 
 
 @contextlib.contextmanager
-def patched_environment(monkeypatch: pytest.MonkeyPatch, environment: Dict[str, str]):
+def patched_environment(monkeypatch: pytest.MonkeyPatch, environment: dict[str, str]):
     with monkeypatch.context() as mp:
         for envvar, val in environment.items():
             mp.setenv(name=envvar, value=val)
@@ -25,7 +24,7 @@ def patched_environment(monkeypatch: pytest.MonkeyPatch, environment: Dict[str,
 
 def test_x86(tmp_path: Path, monkeypatch: pytest.MonkeyPatch):
     arch = "32"
-    environment: Dict[str, str] = {}
+    environment: dict[str, str] = {}
 
     configuration = PythonConfiguration("irrelevant", arch, "irrelevant", None)
 
@@ -39,7 +38,7 @@ def test_x86(tmp_path: Path, monkeypatch: pytest.MonkeyPatch):
 
 def test_x64(tmp_path: Path, monkeypatch: pytest.MonkeyPatch):
     arch = "64"
-    environment: Dict[str, str] = {}
+    environment: dict[str, str] = {}
 
     configuration = PythonConfiguration("irrelevant", arch, "irrelevant", None)
 
@@ -56,7 +55,7 @@ def test_x64(tmp_path: Path, monkeypatch: pytest.MonkeyPatch):
 )
 def test_arm(tmp_path: Path, monkeypatch: pytest.MonkeyPatch):
     arch = "ARM64"
-    environment: Dict[str, str] = {}
+    environment: dict[str, str] = {}
 
     configuration = PythonConfiguration("irrelevant", arch, "irrelevant", None)
 
diff --git a/unit_test/main_tests/conftest.py b/unit_test/main_tests/conftest.py
index 20dfb158d..e39c09446 100644
--- a/unit_test/main_tests/conftest.py
+++ b/unit_test/main_tests/conftest.py
@@ -8,7 +8,7 @@
 
 import pytest
 
-from cibuildwheel import linux, macos, util, windows
+from cibuildwheel import linux, macos, pyodide, util, windows
 
 
 class ArgsInterceptor:
@@ -42,6 +42,7 @@ def ignore_call(*args, **kwargs):
     monkeypatch.setattr(windows, "build", fail_on_call)
     monkeypatch.setattr(linux, "build", fail_on_call)
     monkeypatch.setattr(macos, "build", fail_on_call)
+    monkeypatch.setattr(pyodide, "build", fail_on_call)
 
     monkeypatch.setattr(Path, "mkdir", ignore_call)
 
@@ -88,6 +89,7 @@ def intercepted_build_args(monkeypatch):
     monkeypatch.setattr(linux, "build", intercepted)
     monkeypatch.setattr(macos, "build", intercepted)
     monkeypatch.setattr(windows, "build", intercepted)
+    monkeypatch.setattr(pyodide, "build", intercepted)
 
     yield intercepted
 
diff --git a/unit_test/main_tests/main_options_test.py b/unit_test/main_tests/main_options_test.py
index fe3b21189..572076864 100644
--- a/unit_test/main_tests/main_options_test.py
+++ b/unit_test/main_tests/main_options_test.py
@@ -1,16 +1,16 @@
 from __future__ import annotations
 
 import sys
+import tomllib
 from fnmatch import fnmatch
 from pathlib import Path
 
 import pytest
 
 from cibuildwheel.__main__ import main
-from cibuildwheel._compat import tomllib
 from cibuildwheel.environment import ParsedEnvironment
 from cibuildwheel.options import BuildOptions, _get_pinned_container_images
-from cibuildwheel.util import BuildSelector, resources_dir, split_config_settings
+from cibuildwheel.util import BuildSelector, EnableGroup, resources_dir, split_config_settings
 
 # CIBW_PLATFORM is tested in main_platform_test.py
 
@@ -126,7 +126,7 @@ def get_default_repair_command(platform: str) -> str:
         return "auditwheel repair -w {dest_dir} {wheel}"
     elif platform == "macos":
         return "delocate-wheel --require-archs {delocate_archs} -w {dest_dir} -v {wheel}"
-    elif platform == "windows":
+    elif platform == "windows" or platform == "pyodide":
         return ""
     else:
         msg = f"Unknown platform: {platform!r}"
@@ -368,6 +368,45 @@ def test_debug_traceback(monkeypatch, method, capfd):
         assert "Traceback (most recent call last)" in err
 
 
+@pytest.mark.parametrize("method", ["unset", "command_line", "env_var"])
+def test_enable(method, intercepted_build_args, monkeypatch):
+    if method == "command_line":
+        monkeypatch.setattr(sys, "argv", [*sys.argv, "--enable", "pypy"])
+    elif method == "env_var":
+        monkeypatch.setenv("CIBW_ENABLE", "pypy")
+
+    main()
+
+    enable_groups = intercepted_build_args.args[0].globals.build_selector.enable
+
+    if method == "unset":
+        assert enable_groups == frozenset()
+    else:
+        assert enable_groups == frozenset([EnableGroup.PyPy])
+
+
+def test_enable_arg_inherits(intercepted_build_args, monkeypatch):
+    monkeypatch.setenv("CIBW_ENABLE", "pypy")
+    monkeypatch.setattr(sys, "argv", [*sys.argv, "--enable", "cpython-prerelease"])
+
+    main()
+
+    enable_groups = intercepted_build_args.args[0].globals.build_selector.enable
+
+    assert enable_groups == frozenset((EnableGroup.PyPy, EnableGroup.CPythonPrerelease))
+
+
+def test_enable_arg_error_message(monkeypatch, capsys):
+    monkeypatch.setattr(sys, "argv", [*sys.argv, "--enable", "invalid_group"])
+
+    with pytest.raises(SystemExit) as ex:
+        main()
+    assert ex.value.code == 2
+
+    _, err = capsys.readouterr()
+    assert "Valid group names are:" in err
+
+
 def test_defaults(platform, intercepted_build_args):
     main()
 
diff --git a/unit_test/main_tests/main_platform_test.py b/unit_test/main_tests/main_platform_test.py
index fbc861595..f98e5805f 100644
--- a/unit_test/main_tests/main_platform_test.py
+++ b/unit_test/main_tests/main_platform_test.py
@@ -6,7 +6,7 @@
 
 from cibuildwheel.__main__ import main
 from cibuildwheel.architecture import Architecture
-from cibuildwheel.util import EnableGroups
+from cibuildwheel.util import EnableGroup
 
 from ..conftest import MOCK_PACKAGE_DIR
 
@@ -217,7 +217,7 @@ def test_only_argument(intercepted_build_args, monkeypatch, only, plat):
     assert options.globals.build_selector.skip_config == ""
     assert options.platform == plat
     assert options.globals.architectures == Architecture.all_archs(plat)
-    assert EnableGroups.PyPy in options.globals.build_selector.enable
+    assert EnableGroup.PyPy in options.globals.build_selector.enable
 
 
 @pytest.mark.parametrize("only", ("cp311-manylxinux_x86_64", "some_linux_thing"))
diff --git a/unit_test/option_prepare_test.py b/unit_test/option_prepare_test.py
index 9d6e2c430..deb0c6fba 100644
--- a/unit_test/option_prepare_test.py
+++ b/unit_test/option_prepare_test.py
@@ -14,20 +14,8 @@
 from cibuildwheel.__main__ import main
 from cibuildwheel.oci_container import OCIPlatform
 
-ALL_IDS = {
-    "cp36",
-    "cp37",
-    "cp38",
-    "cp39",
-    "cp310",
-    "cp311",
-    "cp312",
-    "cp313",
-    "pp37",
-    "pp38",
-    "pp39",
-    "pp310",
-}
+DEFAULT_IDS = {"cp36", "cp37", "cp38", "cp39", "cp310", "cp311", "cp312", "cp313"}
+ALL_IDS = DEFAULT_IDS | {"cp313t", "pp37", "pp38", "pp39", "pp310"}
 
 
 @pytest.fixture
@@ -77,7 +65,7 @@ def test_build_default_launches(monkeypatch):
     assert kwargs["container"]["oci_platform"] == OCIPlatform.AMD64
 
     identifiers = {x.identifier for x in kwargs["platform_configs"]}
-    assert identifiers == {f"{x}-manylinux_x86_64" for x in ALL_IDS}
+    assert identifiers == {f"{x}-manylinux_x86_64" for x in DEFAULT_IDS}
 
     kwargs = build_in_container.call_args_list[1][1]
     assert "quay.io/pypa/manylinux2014_i686" in kwargs["container"]["image"]
@@ -85,7 +73,7 @@ def test_build_default_launches(monkeypatch):
     assert kwargs["container"]["oci_platform"] == OCIPlatform.i386
 
     identifiers = {x.identifier for x in kwargs["platform_configs"]}
-    assert identifiers == {f"{x}-manylinux_i686" for x in ALL_IDS}
+    assert identifiers == {f"{x}-manylinux_i686" for x in DEFAULT_IDS}
 
     kwargs = build_in_container.call_args_list[2][1]
     assert "quay.io/pypa/musllinux_1_2_x86_64" in kwargs["container"]["image"]
@@ -93,9 +81,7 @@ def test_build_default_launches(monkeypatch):
     assert kwargs["container"]["oci_platform"] == OCIPlatform.AMD64
 
     identifiers = {x.identifier for x in kwargs["platform_configs"]}
-    assert identifiers == {
-        f"{x}-musllinux_x86_64" for x in ALL_IDS for x in ALL_IDS if "pp" not in x
-    }
+    assert identifiers == {f"{x}-musllinux_x86_64" for x in DEFAULT_IDS}
 
     kwargs = build_in_container.call_args_list[3][1]
     assert "quay.io/pypa/musllinux_1_2_i686" in kwargs["container"]["image"]
@@ -103,7 +89,7 @@ def test_build_default_launches(monkeypatch):
     assert kwargs["container"]["oci_platform"] == OCIPlatform.i386
 
     identifiers = {x.identifier for x in kwargs["platform_configs"]}
-    assert identifiers == {f"{x}-musllinux_i686" for x in ALL_IDS if "pp" not in x}
+    assert identifiers == {f"{x}-musllinux_i686" for x in DEFAULT_IDS}
 
 
 @pytest.mark.usefixtures("mock_build_container")
@@ -117,6 +103,7 @@ def test_build_with_override_launches(monkeypatch, tmp_path):
 [tool.cibuildwheel]
 manylinux-x86_64-image = "manylinux_2_28"
 musllinux-x86_64-image = "musllinux_1_2"
+enable = ["pypy", "cpython-freethreading"]
 
 # Before Python 3.10, use manylinux2014, musllinux_1_1
 [[tool.cibuildwheel.overrides]]
@@ -158,7 +145,7 @@ def test_build_with_override_launches(monkeypatch, tmp_path):
     assert identifiers == {
         f"{x}-manylinux_x86_64"
         for x in ALL_IDS
-        - {"cp36", "cp310", "cp311", "cp312", "cp313", "pp37", "pp38", "pp39", "pp310"}
+        - {"cp36", "cp310", "cp311", "cp312", "cp313", "cp313t", "pp37", "pp38", "pp39", "pp310"}
     }
     assert kwargs["options"].build_options("cp37-manylinux_x86_64").before_all == ""
 
@@ -169,7 +156,7 @@ def test_build_with_override_launches(monkeypatch, tmp_path):
     identifiers = {x.identifier for x in kwargs["platform_configs"]}
     assert identifiers == {
         f"{x}-manylinux_x86_64"
-        for x in ["cp310", "cp311", "cp312", "cp313", "pp37", "pp38", "pp39", "pp310"]
+        for x in ["cp310", "cp311", "cp312", "cp313", "cp313t", "pp37", "pp38", "pp39", "pp310"]
     }
 
     kwargs = build_in_container.call_args_list[3][1]
diff --git a/unit_test/options_test.py b/unit_test/options_test.py
index fb6727b0c..1b9422c9e 100644
--- a/unit_test/options_test.py
+++ b/unit_test/options_test.py
@@ -15,7 +15,7 @@
     Options,
     _get_pinned_container_images,
 )
-from cibuildwheel.util import EnableGroups
+from cibuildwheel.util import EnableGroup
 
 PYPROJECT_1 = """
 [tool.cibuildwheel]
@@ -426,24 +426,32 @@ def test_override_inherit_environment_with_references(tmp_path: Path) -> None:
 
 
 @pytest.mark.parametrize(
-    ("toml_assignment", "env", "expected_result"),
+    ("toml_assignment", "env", "enable_args", "expected_result"),
     [
-        ("", {}, False),
-        ("free-threaded-support = true", {}, True),
-        ("free-threaded-support = false", {}, False),
-        ("", {"CIBW_FREE_THREADED_SUPPORT": "0"}, False),
-        ("", {"CIBW_FREE_THREADED_SUPPORT": "1"}, True),
-        ("free-threaded-support = false", {"CIBW_FREE_THREADED_SUPPORT": "1"}, True),
-        ("free-threaded-support = true", {"CIBW_FREE_THREADED_SUPPORT": "0"}, False),
-        ("free-threaded-support = true", {"CIBW_FREE_THREADED_SUPPORT": ""}, True),
-        ("free-threaded-support = false", {"CIBW_FREE_THREADED_SUPPORT": ""}, False),
+        ("", {}, [], False),
+        ("enable = ['cpython-freethreading']", {}, [], True),
+        ("enable = []", {}, [], False),
+        ("", {}, ["cpython-freethreading"], True),
+        ("", {}, ["cpython-freethreading", "pypy"], True),
+        ("", {"CIBW_ENABLE": "pypy"}, [], False),
+        ("", {"CIBW_ENABLE": "cpython-freethreading"}, [], True),
+        ("enable = []", {"CIBW_ENABLE": "cpython-freethreading"}, [], True),
+        ("enable = ['cpython-freethreading']", {"CIBW_ENABLE": "pypy"}, [], True),
+        ("enable = ['cpython-freethreading']", {}, ["pypy"], True),
+        ("enable = ['cpython-freethreading']", {"CIBW_ENABLE": ""}, [], True),
+        ("enable = []", {"CIBW_ENABLE": ""}, [], False),
     ],
 )
 def test_free_threaded_support(
-    tmp_path: Path, toml_assignment: str, env: dict[str, str], expected_result: bool
+    tmp_path: Path,
+    toml_assignment: str,
+    env: dict[str, str],
+    enable_args: list[str],
+    expected_result: bool,
 ) -> None:
     args = CommandLineArguments.defaults()
     args.package_dir = tmp_path
+    args.enable = enable_args
 
     pyproject_toml: Path = tmp_path / "pyproject.toml"
     pyproject_toml.write_text(
@@ -456,6 +464,6 @@ def test_free_threaded_support(
     )
     options = Options(platform="linux", command_line_arguments=args, env=env)
     if expected_result:
-        assert EnableGroups.CPythonFreeThreading in options.globals.build_selector.enable
+        assert EnableGroup.CPythonFreeThreading in options.globals.build_selector.enable
     else:
-        assert EnableGroups.CPythonFreeThreading not in options.globals.build_selector.enable
+        assert EnableGroup.CPythonFreeThreading not in options.globals.build_selector.enable
diff --git a/unit_test/projectfiles_test.py b/unit_test/projectfiles_test.py
index 179f648ef..77ea78cf1 100644
--- a/unit_test/projectfiles_test.py
+++ b/unit_test/projectfiles_test.py
@@ -1,10 +1,10 @@
 from __future__ import annotations
 
+import tomllib
 from textwrap import dedent
 
 import pytest
 
-from cibuildwheel._compat import tomllib
 from cibuildwheel.projectfiles import (
     get_requires_python_str,
     resolve_dependency_groups,
diff --git a/unit_test/validate_schema_test.py b/unit_test/validate_schema_test.py
index bb102bb25..c0dfad454 100644
--- a/unit_test/validate_schema_test.py
+++ b/unit_test/validate_schema_test.py
@@ -1,13 +1,12 @@
 from __future__ import annotations
 
 import re
+import tomllib
 from pathlib import Path
 
 import pytest
 import validate_pyproject.api
 
-from cibuildwheel._compat import tomllib
-
 DIR = Path(__file__).parent.resolve()