Update pre-commit

Remove python3.8 leftovers
Add prog to create_argparser
Remove metavar usage from BooleanOptionalAction

.github/workflows/build.yaml

@@ -13,7 +13,7 @@ jobs:
     runs-on: ${{ matrix.os }}
     strategy:
       matrix:
-        python_version: ['3.8', '3.9','3.10','3.11']
+        python_version: ['3.9','3.10','3.11','3.13']
         os: [ubuntu-latest]
 
     steps:

.pre-commit-config.yaml

@@ -1,6 +1,6 @@
 repos:
 -   repo: https://github.com/pre-commit/pre-commit-hooks
-    rev: v4.6.0
+    rev: v6.0.0
     hooks:
     -   id: trailing-whitespace
     -   id: end-of-file-fixer
@@ -10,38 +10,39 @@ repos:
     -   id: name-tests-test
     -   id: requirements-txt-fixer
 -   repo: https://github.com/asottile/setup-cfg-fmt
-    rev: v2.5.0
+    rev: v2.8.0
     hooks:
     -   id: setup-cfg-fmt
 -   repo: https://github.com/asottile/reorder-python-imports
-    rev: v3.12.0
+    rev: v3.15.0
     hooks:
     -   id: reorder-python-imports
         args: [--py38-plus, --add-import, 'from __future__ import annotations']
 -   repo: https://github.com/asottile/add-trailing-comma
-    rev: v3.1.0
+    rev: v3.2.0
     hooks:
     -   id: add-trailing-comma
         args: [--py36-plus]
 -   repo: https://github.com/asottile/dead
-    rev: v1.5.2
+    rev: v2.1.0
     hooks:
     -   id: dead
 -   repo: https://github.com/asottile/pyupgrade
-    rev: v3.15.2
+    rev: v3.20.0
     hooks:
     -   id: pyupgrade
         args: [--py38-plus]
+        exclude: tests
 -   repo: https://github.com/hhatto/autopep8
-    rev: v2.1.0
+    rev: v2.3.2
     hooks:
     -   id: autopep8
 -   repo: https://github.com/PyCQA/flake8
-    rev: 7.0.0
+    rev: 7.3.0
     hooks:
     -   id: flake8
         additional_dependencies: [flake8-encodings, flake8-warnings, flake8-builtins, flake8-print]
 -   repo: https://github.com/pre-commit/mirrors-mypy
-    rev: v1.10.0
+    rev: v1.17.1
     hooks:
     -   id: mypy

settngs/__init__.py

@@ -10,84 +10,38 @@ import re
 import sys
 import typing
 import warnings
+from argparse import BooleanOptionalAction
 from argparse import Namespace
 from collections import defaultdict
 from collections.abc import Sequence
+from collections.abc import Set
+from enum import Enum
+from types import GenericAlias as types_GenericAlias
 from typing import Any
 from typing import Callable
 from typing import cast
+from typing import Collection
 from typing import Dict
 from typing import Generic
+from typing import get_args
+from typing import Mapping
 from typing import NoReturn
+from typing import Tuple
 from typing import TYPE_CHECKING
 from typing import TypeVar
 from typing import Union
 
 logger = logging.getLogger(__name__)
 
+NoneType = type(None)
+
 if sys.version_info < (3, 11):  # pragma: no cover
     from typing_extensions import NamedTuple
 else:  # pragma: no cover
     from typing import NamedTuple
 
 
-if sys.version_info < (3, 9):  # pragma: no cover
-    from typing import List
-    from typing import _GenericAlias as types_GenericAlias
-
-    def removeprefix(self: str, prefix: str, /) -> str:
-        if self.startswith(prefix):
-            return self[len(prefix):]
-        else:
-            return self[:]
-
-    class BooleanOptionalAction(argparse.Action):
-        def __init__(
-            self,
-            option_strings,
-            dest,
-            default=None,
-            type=None,  # noqa: A002
-            choices=None,
-            required=False,
-            help=None,  # noqa: A002
-            metavar=None,
-        ):
-
-            _option_strings = []
-            for option_string in option_strings:
-                _option_strings.append(option_string)
-
-                if option_string.startswith('--'):
-                    option_string = '--no-' + option_string[2:]
-                    _option_strings.append(option_string)
-
-            if help is not None and default is not None and default is not argparse.SUPPRESS:
-                help += ' (default: %(default)s)'
-
-            super().__init__(
-                option_strings=_option_strings,
-                dest=dest,
-                nargs=0,
-                default=default,
-                type=type,
-                choices=choices,
-                required=required,
-                help=help,
-                metavar=metavar,
-            )
-
-        def __call__(self, parser, namespace, values, option_string=None):  # dead: disable
-            if option_string in self.option_strings:
-                setattr(namespace, self.dest, not option_string.startswith('--no-'))
-else:  # pragma: no cover
-    List = list
-    from types import GenericAlias as types_GenericAlias
-    from argparse import BooleanOptionalAction
-    removeprefix = str.removeprefix
-
-
-def _isnamedtupleinstance(x: Any) -> bool:
+def _isnamedtupleinstance(x: Any) -> bool:  # pragma: no cover
     t = type(x)
     b = t.__bases__
 
@@ -208,57 +162,114 @@ class Setting:
             return NotImplemented
         return self.__dict__ == other.__dict__
 
-    def _guess_type(self) -> type | str | None:
-        if self.type is None and self.action is None:
-            if self.cmdline:
-                if self.nargs in ('+', '*') or isinstance(self.nargs, int) and self.nargs > 1:
-                    return List[str]
-                return str
-            else:
-                if not self.cmdline and self.default is not None:
-                    if not isinstance(self.default, str) and not _isnamedtupleinstance(self.default) and isinstance(self.default, Sequence) and self.default and self.default[0]:
-                        try:
-                            return cast(type, type(self.default)[type(self.default[0])])
-                        except Exception:
-                            ...
-                    return type(self.default)
-                return 'Any'
+    __no_type = object()
 
+    def _guess_collection(self) -> tuple[type | str | None, bool]:
+        def get_item_type(x: Any) -> type | None:
+            if x is None or not isinstance(x, (Set, Sequence)) or len(x) == 0:
+                t = self._process_type()  # Specifically this is needed when using the extend action
+                if typing.get_args(t):  # We need the item type not the type of the collection
+                    return typing.get_args(t)[0]  # type: ignore[no-any-return]
+
+                # Return None so that we get the default
+                return None if t is None else self.__no_type  # type: ignore[return-value]
+            if isinstance(x, Set):
+                return type(next(iter(x)))
+            return type(x[0])
+
+        try:
+            list_type = self._process_type()
+            # if the type is a generic alias than return it immediately
+            if isinstance(list_type, types_GenericAlias) and issubclass(list_type.__origin__, Collection):
+                return list_type, self.default is None
+
+            if list_type is NoneType:
+                list_type = None
+            if list_type is None and self.default is not None:
+                list_type = type(self.default)
+
+            # Default to a list if we don't know what type of collection this is
+            if list_type is None or not issubclass(list_type, Collection) or issubclass(list_type, Enum):
+                list_type = list
+
+            # Get the item type (int) in list[int]
+            it = get_item_type(self.default)
+            if isinstance(self.type, type):
+                it = self.type
+
+            if it is self.__no_type:
+                return self._process_type() or list[str], self.default is None
+
+            # Try to get the generic alias for this type
+            if it is not None:
+                try:
+                    ret = cast(type, list_type[it]), self.default is None  # type: ignore[index]
+                    return ret
+                except Exception:
+                    ...
+
+            # Fall back to list[str] if anything fails
+            return cast(type, list_type[str]), self.default is None  # type: ignore[index]
+        except Exception:
+            return None, self.default is None
+
+    def _process_type(self) -> type | None:
+        if self.type is None:
+            return None
         if isinstance(self.type, type):
             return self.type
 
-        if self.type is not None:
-            type_hints = typing.get_type_hints(self.type)
-            if 'return' in type_hints:
-                t: type | str = type_hints['return']
-                return t
-            if self.default is not None:
-                if not isinstance(self.default, str) and not _isnamedtupleinstance(self.default) and isinstance(self.default, Sequence) and self.default and self.default[0]:
-                    try:
-                        return cast(type, type(self.default)[type(self.default[0])])
-                    except Exception:
-                        ...
-                return type(self.default)
-            return 'Any'
+        return cast(dict[str, type], typing.get_type_hints(self.type)).get('return', None)
 
-        if self.action in ('store_true', 'store_false', BooleanOptionalAction):
-            return bool
+    def _guess_type_internal(self) -> tuple[type | str | None, bool]:
+        default_is_none = self.default is None
+        __action_to_type = {
+            'store_true': (bool, False),
+            'store_false': (bool, False),
+            BooleanOptionalAction: (bool, default_is_none),
+            'store_const': (type(self.const), default_is_none),
+            'count': (int, default_is_none),
+            'extend': self._guess_collection(),
+            'append_const': (cast(type, list[type(self.const)]), default_is_none),  # type: ignore[misc]
+            'help': (None, default_is_none),
+            'version': (None, default_is_none),
+        }
 
-        if self.action in ('store_const',):
-            return type(self.const)
+        # Process standard actions
+        if self.action in __action_to_type:
+            return __action_to_type[self.action]
 
-        if self.action in ('count',):
-            return int
+        # nargs > 1 is always a list
+        if self.nargs in ('+', '*') or isinstance(self.nargs, int) and self.nargs > 1:
+            return self._guess_collection()
 
-        if self.action in ('append', 'extend'):
-            return List[str]
+        # Process the type argument
+        type_type = self._process_type()
+        if type_type is not None:
+            return type_type, default_is_none
 
-        if self.action in ('append_const',):
-            return list  # list[type(self.const)]
+        # Check if a default value was given.
+        if self.default is not None:
+            if not isinstance(self.default, str) and not _isnamedtupleinstance(self.default) and isinstance(self.default, (Set, Sequence)):
+                return self._guess_collection()
+            # The type argument will convert this if it is a string. We only get here if type is a function without type hints
+            if not (isinstance(self.default, str) and self.type is not None):
+                return type(self.default), default_is_none
 
-        if self.action in ('help', 'version'):
-            return None
-        return 'Any'
+        # There is no way to detemine the type from an action
+        if callable(self.action):
+            return 'Any', default_is_none
+
+        # Finally if this is a commandline argument it will default to a string
+        if self.cmdline and self.type is None:
+            return str, default_is_none
+        # For file only settings it will default to Any
+        return 'Any', default_is_none
+
+    def _guess_type(self) -> tuple[type | str | None, bool]:
+        if self.action == 'append':
+            return cast(type, list[self._guess_type_internal()[0]]), self.default is None  # type: ignore[misc]
+        return self._guess_type_internal()
 
     def get_dest(self, prefix: str, names: Sequence[str], dest: str | None) -> tuple[str, str, str, bool]:
         setting_name = None
@@ -292,7 +303,7 @@ class Setting:
         return self.argparse_args, self.filter_argparse_kwargs()
 
 
-class TypedNS:
+class TypedNS():
     def __init__(self) -> None:
         raise TypeError('TypedNS cannot be instantiated')
 
@@ -302,7 +313,8 @@ class Group(NamedTuple):
     v: dict[str, Setting]
 
 
-Values = Dict[str, Dict[str, Any]]
+Values = Mapping[str, Any]
+_values = Dict[str, Dict[str, Any]]
 Definitions = Dict[str, Group]
 
 T = TypeVar('T', bound=Union[Values, Namespace, TypedNS])
@@ -315,7 +327,45 @@ class Config(NamedTuple, Generic[T]):
 
 if TYPE_CHECKING:
     ArgParser = Union[argparse._MutuallyExclusiveGroup, argparse._ArgumentGroup, argparse.ArgumentParser]
-    ns = Namespace | TypedNS | Config[T] | None
+    ns = Union[TypedNS, Config[T], None]
+
+
+def _get_import(t: type) -> tuple[str, str]:
+    type_name = t.__name__
+    import_needed = ''
+    # Builtin types don't need an import
+    if t.__module__ != 'builtins':
+        import_needed = f'import {t.__module__}'
+        # Use the full imported name
+        type_name = t.__module__ + '.' + type_name
+    return type_name, import_needed
+
+
+def _type_to_string(t: type | str) -> tuple[str, str]:
+    type_name = 'Any'
+    import_needed = ''
+    # Take a string as is
+    if isinstance(t, str):
+        type_name = t
+    # Handle generic aliases eg dict[str, str] instead of dict
+    elif isinstance(t, types_GenericAlias):
+        args = get_args(t)
+        if args:
+            import_needed = ''
+            for arg in args:
+                _, arg_import = _get_import(arg)
+                import_needed += '\n' + arg_import
+        else:
+            t = t.__origin__.__name__
+        type_name = str(t)
+    # Handle standard type objects
+    elif isinstance(t, type):
+        type_name, import_needed = _get_import(t)
+
+    # Expand Any to typing.Any
+    if type_name == 'Any':
+        type_name = 'typing.Any'
+    return type_name.strip(), import_needed.strip()
 
 
 def generate_ns(definitions: Definitions) -> tuple[str, str]:
@@ -324,35 +374,21 @@ def generate_ns(definitions: Definitions) -> tuple[str, str]:
     imports = set()
 
     attributes = []
+    used_attributes: set[str] = set()
     for group in definitions.values():
         for setting in group.v.values():
-            t = setting._guess_type()
+            t, noneable = setting._guess_type()
             if t is None:
                 continue
-            # Default to any
-            type_name = 'Any'
+            type_name, import_needed = _type_to_string(t)
+            imports.add(import_needed)
 
-            # Take a string as is
-            if isinstance(t, str):
-                type_name = t
-            # Handle generic aliases eg dict[str, str] instead of dict
-            elif isinstance(t, types_GenericAlias):
-                type_name = str(t)
-            # Handle standard type objects
-            elif isinstance(t, type):
-                type_name = t.__name__
-                # Builtin types don't need an import
-                if t.__module__ != 'builtins':
-                    imports.add(f'import {t.__module__}')
-                    # Use the full imported name
-                    type_name = t.__module__ + '.' + type_name
-
-            # Expand Any to typing.Any
-            if type_name == 'Any':
-                type_name = 'typing.Any'
-
-            attribute = f'    {setting.internal_name}: {type_name}'
-            if attribute not in attributes:
+            if noneable and type_name not in ('typing.Any', 'None'):
+                attribute = f'    {setting.internal_name}: {type_name} | None'
+            else:
+                attribute = f'    {setting.internal_name}: {type_name}'
+            if setting.internal_name not in used_attributes:
+                used_attributes.add(setting.internal_name)
                 attributes.append(attribute)
         # Add a blank line between groups
         if attributes and attributes[-1] != '':
@@ -369,7 +405,7 @@ def generate_ns(definitions: Definitions) -> tuple[str, str]:
         initial_imports.append('import typing')
 
     # Remove the possible duplicate typing import
-    imports = sorted(list(imports - {'import typing'}))
+    imports = sorted(imports - {'import typing', ''})
 
     # Merge the imports the ns class definition and the attributes
     return '\n'.join(initial_imports + imports), ns + '\n'.join(attributes)
@@ -384,34 +420,20 @@ def generate_dict(definitions: Definitions) -> tuple[str, str]:
     classes = []
     for group_name, group in definitions.items():
         attributes = []
+        used_attributes: set[str] = set()
         for setting in group.v.values():
-            t = setting._guess_type()
+            t, no_default = setting._guess_type()
             if t is None:
                 continue
-            # Default to any
-            type_name = 'Any'
+            type_name, import_needed = _type_to_string(t)
+            imports.add(import_needed)
 
-            # Take a string as is
-            if isinstance(t, str):
-                type_name = t
-            # Handle generic aliases eg dict[str, str] instead of dict
-            elif isinstance(t, types_GenericAlias):
-                type_name = str(t)
-            # Handle standard type objects
-            elif isinstance(t, type):
-                type_name = t.__name__
-                # Builtin types don't need an import
-                if t.__module__ != 'builtins':
-                    imports.add(f'import {t.__module__}')
-                    # Use the full imported name
-                    type_name = t.__module__ + '.' + type_name
-
-            # Expand Any to typing.Any
-            if type_name == 'Any':
-                type_name = 'typing.Any'
-
-            attribute = f'    {setting.dest}: {type_name}'
-            if attribute not in attributes:
+            if no_default and type_name not in ('typing.Any', 'None'):
+                attribute = f'    {setting.dest}: {type_name} | None'
+            else:
+                attribute = f'    {setting.dest}: {type_name}'
+            if setting.dest not in used_attributes:
+                used_attributes.add(setting.dest)
                 attributes.append(attribute)
         if not attributes or all(x == '' for x in attributes):
             attributes = ['    ...']
@@ -421,7 +443,7 @@ def generate_dict(definitions: Definitions) -> tuple[str, str]:
         )
 
     # Remove the possible duplicate typing import
-    imports = sorted(list(imports - {'import typing'}))
+    imports = sorted(list(imports - {'import typing', ''}))
 
     if groups_are_identifiers:
         ns = '\nclass SettngsDict(typing.TypedDict):\n'
@@ -475,7 +497,7 @@ def get_options(config: Config[T], group: str) -> dict[str, Any]:
                 if name in internal_names:
                     values[internal_names[name].dest] = value
                 else:
-                    values[removeprefix(name, f'{group}').lstrip('_')] = value
+                    values[name.removeprefix(f'{group}').lstrip('_')] = value
     return values
 
 
@@ -526,7 +548,7 @@ def normalize_config(
     if not file and not cmdline:
         raise ValueError('Invalid parameters: you must set either file or cmdline to True')
 
-    normalized: Values = {}
+    normalized: dict[str, dict[str, Any]] = {}
     options = config.values
     definitions = _get_internal_definitions(config=config, persistent=persistent)
     for group_name, group in definitions.items():
@@ -594,7 +616,7 @@ def clean_config(
         persistent: Include unknown keys in persistent groups and unknown groups
     """
 
-    cleaned, _ = normalize_config(config, file=file, cmdline=cmdline, default=default, persistent=persistent)
+    cleaned, _ = cast(Config[_values], normalize_config(config, file=file, cmdline=cmdline, default=default, persistent=persistent))
     for group in list(cleaned.keys()):
         if not cleaned[group]:
             del cleaned[group]
@@ -682,11 +704,12 @@ def save_file(
     return True
 
 
-def create_argparser(definitions: Definitions, description: str, epilog: str) -> argparse.ArgumentParser:
+def create_argparser(definitions: Definitions, description: str, epilog: str, *, prog: str | None = None) -> argparse.ArgumentParser:
     """Creates an :class:`argparse.ArgumentParser` from all cmdline settings"""
     groups: dict[str, ArgParser] = {}
     argparser = argparse.ArgumentParser(
         description=description, epilog=epilog, formatter_class=argparse.RawTextHelpFormatter,
+        prog=prog,
     )
 
     def get_current_group(setting: Setting) -> ArgParser:
@@ -727,6 +750,8 @@ def parse_cmdline(
     epilog: str,
     args: list[str] | None = None,
     config: ns[T] = None,
+    *,
+    prog: str | None = None,
 ) -> Config[Values]:
     """
     Creates an `argparse.ArgumentParser` from cmdline settings in `self.definitions`.
@@ -748,7 +773,7 @@ def parse_cmdline(
     else:
         namespace = config
 
-    argparser = create_argparser(definitions, description, epilog)
+    argparser = create_argparser(definitions, description, epilog, prog=prog)
     ns = argparser.parse_args(args, namespace=namespace)
 
     return normalize_config(Config(ns, definitions), cmdline=True, file=True)
@@ -785,11 +810,12 @@ def parse_config(
 class Manager:
     """docstring for Manager"""
 
-    def __init__(self, description: str = '', epilog: str = '', definitions: Definitions | Config[T] | None = None):
+    def __init__(self, description: str = '', epilog: str = '', definitions: Definitions | Config[T] | None = None, *, prog: str | None = None):
         # This one is never used, it just makes MyPy happy
         self.argparser = argparse.ArgumentParser(description=description, epilog=epilog)
         self.description = description
         self.epilog = epilog
+        self.prog = prog
 
         self.definitions: Definitions
         if isinstance(definitions, Config):
@@ -812,7 +838,7 @@ class Manager:
         return generate_dict(self.definitions)
 
     def create_argparser(self) -> None:
-        self.argparser = create_argparser(self.definitions, self.description, self.epilog)
+        self.argparser = create_argparser(self.definitions, self.description, self.epilog, prog=self.prog)
 
     def add_setting(self, *args: Any, **kwargs: Any) -> None:
         """Passes all arguments through to `Setting`, `group` and `exclusive` are already set"""
@@ -1024,7 +1050,6 @@ def example_group(manager: Manager) -> None:
     manager.add_setting(
         '--verbose', '-v',
         default=False,
-        metavar='nothing',
         action=BooleanOptionalAction,  # Added in Python 3.9
     )
 
@@ -1037,6 +1062,32 @@ def persistent_group(manager: Manager) -> None:
     )
 
 
+class SettngsNS(TypedNS):
+    Example_Group__hello: str
+    Example_Group__save: bool
+    Example_Group__verbose: bool
+
+    persistent__test: bool
+
+
+class Example_Group(typing.TypedDict):
+    hello: str
+    save: bool
+    verbose: bool
+
+
+class persistent(typing.TypedDict):
+    test: bool
+
+
+SettngsDict = typing.TypedDict(
+    'SettngsDict', {
+        'Example Group': Example_Group,
+        'persistent': persistent,
+    },
+)
+
+
 def _main(args: list[str] | None = None) -> None:
     settings_path = pathlib.Path('./settings.json')
     manager = Manager(description='This is an example', epilog='goodbye!')
@@ -1044,11 +1095,11 @@ def _main(args: list[str] | None = None) -> None:
     manager.add_group('Example Group', example_group)
     manager.add_persistent_group('persistent', persistent_group)
 
-    file_config, success = manager.parse_file(settings_path)
+    file_config, success = cast(Tuple[Config[SettngsDict], bool], manager.parse_file(settings_path))
     file_namespace = manager.get_namespace(file_config, file=True, cmdline=True)
 
-    merged_config = manager.parse_cmdline(args=args, config=file_namespace)
-    merged_namespace = manager.get_namespace(merged_config, file=True, cmdline=True)
+    merged_config = cast(Config[SettngsDict], manager.parse_cmdline(args=args, config=file_namespace))
+    merged_namespace = cast(Config[SettngsNS], manager.get_namespace(merged_config, file=True, cmdline=True))
 
     print(f'Hello {merged_config.values["Example Group"]["hello"]}')  # noqa: T201
     if merged_namespace.values.Example_Group__save:

setup.cfg

@@ -9,7 +9,6 @@ author_email = timmy@narnian.us
 license = MIT
 license_files = LICENSE
 classifiers =
-    License :: OSI Approved :: MIT License
     Programming Language :: Python :: 3
     Programming Language :: Python :: 3 :: Only
     Programming Language :: Python :: Implementation :: CPython
@@ -19,7 +18,7 @@ classifiers =
 packages = find:
 install_requires =
     typing-extensions>=4.3.0;python_version < '3.11'
-python_requires = >=3.8
+python_requires = >=3.9
 include_package_data = True
 
 [options.packages.find]
@@ -31,7 +30,7 @@ exclude =
 settngs = py.typed
 
 [tox:tox]
-envlist = py3.8,py3.9,py3.10,py3.11,py3.12,pypy3
+envlist = py3.9,py3.10,py3.11,py3.12,py3.13,pypy3
 
 [testenv]
 deps = -rrequirements-dev.txt

tests/settngs_test.py

@@ -2,11 +2,13 @@ from __future__ import annotations
 
 import argparse
 import ast
+from enum import Enum, auto
 import json
 import pathlib
 import sys
 from collections import defaultdict
 from typing import Generator
+from typing import NamedTuple
 
 import pytest
 
@@ -19,6 +21,7 @@ from testing.settngs import success
 
 if sys.version_info >= (3, 10):  # pragma: no cover
     List = list
+    Set = set
     help_output = '''\
 usage: __main__.py [-h] [TEST ...]
 
@@ -28,20 +31,9 @@ positional arguments:
 options:
   -h, --help  show this help message and exit
 '''
-elif sys.version_info < (3, 9):  # pragma: no cover
-    from typing import List
-    help_output = '''\
-usage: __main__.py [-h] [TEST [TEST ...]]
-
-positional arguments:
-  TEST
-
-optional arguments:
-  -h, --help  show this help message and exit
-'''
-
 else:  # pragma: no cover
     List = list
+    Set = set
     help_output = '''\
 usage: __main__.py [-h] [TEST ...]
 
@@ -123,12 +115,14 @@ def test_exclusive_group(settngs_manager):
     with pytest.raises(SystemExit):
         settngs_manager.add_group('tst', lambda parser: parser.add_setting('--test2', default='hello'), exclusive_group=True)
         settngs_manager.create_argparser()
-        args = settngs_manager.argparser.parse_args(['--test', 'never', '--test2', 'never'])
+        args = settngs_manager.argparser.parse_args(['__main__.py', '--test', 'never', '--test2', 'never'])
 
 
 def test_files_group(capsys, settngs_manager):
     settngs_manager.add_group('runtime', lambda parser: parser.add_setting('test', default='hello', nargs='*'))
+    settngs_manager.prog = '__main__.py'
     settngs_manager.create_argparser()
+    settngs_manager.prog = '__main__.py'
     settngs_manager.argparser.print_help()
     captured = capsys.readouterr()
     assert captured.out == help_output
@@ -136,7 +130,9 @@ def test_files_group(capsys, settngs_manager):
 
 def test_setting_without_group(capsys, settngs_manager):
     settngs_manager.add_setting('test', default='hello', nargs='*')
+    settngs_manager.prog = '__main__.py'
     settngs_manager.create_argparser()
+    settngs_manager.prog = '__main__.py'
     settngs_manager.argparser.print_help()
     captured = capsys.readouterr()
     assert captured.out == help_output
@@ -255,7 +251,7 @@ class TestValues:
         # manager_unknown.add_persistent_group('persistent', lambda parser: parser.add_setting('--world', default='world'))
 
         defaults = manager.defaults()
-        defaults.values['test'] = 'fail'  # type: ignore[assignment] # Not defined in manager, should be removed
+        defaults.values['test'] = 'fail'  # type: ignore[index] # Not defined in manager, should be removed
         defaults.values['persistent']['hello'] = 'success'  # Group is not defined in manager_unknown, should stay
 
         normalized, _ = manager_unknown.normalize_config(defaults.values, file=True)
@@ -610,6 +606,10 @@ def test_adding_to_existing_persistent_group(settngs_manager: settngs.Manager, t
     assert default_to_regular(settngs_manager.definitions) == default_to_regular(settngs_manager2.definitions)
 
 
+class test_enum(Enum):
+    test = auto()
+
+
 class test_type(int):
     ...
 
@@ -618,6 +618,18 @@ def _typed_function(something: str) -> test_type:  # pragma: no cover
     return test_type()
 
 
+def _typed_list_generic_function(something: test_type) -> List[test_type]:  # pragma: no cover
+    return [test_type()]
+
+
+def _typed_list_function() -> List:   # type: ignore[type-arg] # pragma: no cover
+    return []
+
+
+def _typed_set_function() -> Set:  # type: ignore[type-arg] # pragma: no cover
+    return set()
+
+
 def _untyped_function(something):
     ...
 
@@ -644,37 +656,59 @@ class _customAction(argparse.Action):  # pragma: no cover
             help=help,
         )
 
-    def __call__(self, parser, namespace, values, option_string=None):
+    def __call__(self, parser, namespace, values, option_string=None):  # pragma: no cover
         setattr(namespace, self.dest, 'Something')
 
 
 types = (
-    (0, settngs.Setting('-t', '--test'), str),
-    (1, settngs.Setting('-t', '--test', cmdline=False), 'Any'),
-    (2, settngs.Setting('-t', '--test', default=1, file=True, cmdline=False), int),
-    (3, settngs.Setting('-t', '--test', action='count'), int),
-    (4, settngs.Setting('-t', '--test', action='append'), List[str]),
-    (5, settngs.Setting('-t', '--test', action='extend'), List[str]),
-    (6, settngs.Setting('-t', '--test', nargs='+'), List[str]),
-    (7, settngs.Setting('-t', '--test', action='store_const', const=1), int),
-    (8, settngs.Setting('-t', '--test', action='append_const', const=1), list),
-    (9, settngs.Setting('-t', '--test', action='store_true'), bool),
-    (10, settngs.Setting('-t', '--test', action='store_false'), bool),
-    (11, settngs.Setting('-t', '--test', action=settngs.BooleanOptionalAction), bool),
-    (12, settngs.Setting('-t', '--test', action=_customAction), 'Any'),
-    (13, settngs.Setting('-t', '--test', action='help'), None),
-    (14, settngs.Setting('-t', '--test', action='version'), None),
-    (15, settngs.Setting('-t', '--test', type=int), int),
-    (16, settngs.Setting('-t', '--test', type=_typed_function), test_type),
-    (17, settngs.Setting('-t', '--test', type=_untyped_function, default=1), int),
-    (18, settngs.Setting('-t', '--test', type=_untyped_function), 'Any'),
+    (0, settngs.Setting('-t', '--test'), str, True),
+    (1, settngs.Setting('-t', '--test', cmdline=False), 'Any', True),
+    (2, settngs.Setting('-t', '--test', default=1, file=True, cmdline=False), int, False),
+    (3, settngs.Setting('-t', '--test', default='test'), str, False),
+    (4, settngs.Setting('-t', '--test', default='test', file=True, cmdline=False), str, False),
+    (5, settngs.Setting('-t', '--test', action='count'), int, True),
+    (6, settngs.Setting('-t', '--test', action='append'), List[str], True),
+    (7, settngs.Setting('-t', '--test', action='extend'), List[str], True),
+    (8, settngs.Setting('-t', '--test', nargs='+'), List[str], True),
+    (9, settngs.Setting('-t', '--test', nargs='+', type=pathlib.Path), List[pathlib.Path], True),
+    (10, settngs.Setting('-t', '--test', nargs='+', type=test_enum), List[test_enum], True),
+    (11, settngs.Setting('-t', '--test', action='store_const', const=1), int, True),
+    (12, settngs.Setting('-t', '--test', action='append_const', const=1), List[int], True),
+    (13, settngs.Setting('-t', '--test', action='store_true'), bool, False),
+    (14, settngs.Setting('-t', '--test', action='store_false'), bool, False),
+    (15, settngs.Setting('-t', '--test', action=argparse.BooleanOptionalAction), bool, True),
+    (16, settngs.Setting('-t', '--test', action=_customAction), 'Any', True),
+    (17, settngs.Setting('-t', '--test', type=test_enum), test_enum, True),
+    (18, settngs.Setting('-t', '--test', type=int), int, True),
+    (19, settngs.Setting('-t', '--test', type=int, nargs='+'), List[int], True),
+    (20, settngs.Setting('-t', '--test', type=_typed_function), test_type, True),
+    (21, settngs.Setting('-t', '--test', type=_untyped_function, default=1), int, False),
+    (22, settngs.Setting('-t', '--test', type=_untyped_function, default=[1]), List[int], False),
+    (23, settngs.Setting('-t', '--test', type=_untyped_function), 'Any', True),
+    (24, settngs.Setting('-t', '--test', type=_untyped_function, default={1}), Set[int], False),
+    (25, settngs.Setting('-t', '--test', action='append', type=int), List[int], True),
+    (26, settngs.Setting('-t', '--test', action='extend', type=int, nargs=2), List[int], True),
+    (27, settngs.Setting('-t', '--test', action='append', type=int, nargs=2), List[List[int]], True),
+    (28, settngs.Setting('-t', '--test', action='extend', nargs='+'), List[str], True),
+    (29, settngs.Setting('-t', '--test', action='extend', type=_typed_list_generic_function), List[test_type], True),
+    (30, settngs.Setting('-t', '--test', action='extend', type=_typed_list_function), List, True),
+    (31, settngs.Setting('-t', '--test', action='extend', type=_typed_set_function), Set, True),
+    (32, settngs.Setting('-t', '--test', action='help'), None, True),
+    (33, settngs.Setting('-t', '--test', action='version'), None, True),
 )
 
 
-@pytest.mark.parametrize('num,setting,typ', types)
-def test_guess_type(num, setting, typ):
-    guessed_type = setting._guess_type()
+@pytest.mark.parametrize('num,setting,typ,noneable_expected', types)
+def test_guess_type(num, setting, typ, noneable_expected):
+    x = setting._guess_type()
+    guessed_type, noneable = x
     assert guessed_type == typ
+    assert noneable == noneable_expected
+
+
+class TypeResult(NamedTuple):
+    extra_imports: str
+    typ: str
 
 
 expected_src = '''from __future__ import annotations
@@ -685,34 +719,40 @@ import settngs
 class SettngsNS(settngs.TypedNS):
     test__test: {typ}
 '''
-no_type_expected_src = '''from __future__ import annotations
 
-import settngs
-
-
-class SettngsNS(settngs.TypedNS):
-    ...
-'''
 settings = (
-    (0, lambda parser: parser.add_setting('-t', '--test'), expected_src.format(extra_imports='', typ='str')),
-    (1, lambda parser: parser.add_setting('-t', '--test', cmdline=False), expected_src.format(extra_imports='import typing\n', typ='typing.Any')),
-    (2, lambda parser: parser.add_setting('-t', '--test', default=1, file=True, cmdline=False), expected_src.format(extra_imports='', typ='int')),
-    (3, lambda parser: parser.add_setting('-t', '--test', action='count'), expected_src.format(extra_imports='', typ='int')),
-    (4, lambda parser: parser.add_setting('-t', '--test', action='append'), expected_src.format(extra_imports='import typing\n' if sys.version_info < (3, 9) else '', typ='typing.List[str]' if sys.version_info < (3, 9) else 'list[str]')),
-    (5, lambda parser: parser.add_setting('-t', '--test', action='extend'), expected_src.format(extra_imports='import typing\n' if sys.version_info < (3, 9) else '', typ='typing.List[str]' if sys.version_info < (3, 9) else 'list[str]')),
-    (6, lambda parser: parser.add_setting('-t', '--test', nargs='+'), expected_src.format(extra_imports='import typing\n' if sys.version_info < (3, 9) else '', typ='typing.List[str]' if sys.version_info < (3, 9) else 'list[str]')),
-    (7, lambda parser: parser.add_setting('-t', '--test', action='store_const', const=1), expected_src.format(extra_imports='', typ='int')),
-    (8, lambda parser: parser.add_setting('-t', '--test', action='append_const', const=1), expected_src.format(extra_imports='', typ='list')),
-    (9, lambda parser: parser.add_setting('-t', '--test', action='store_true'), expected_src.format(extra_imports='', typ='bool')),
-    (10, lambda parser: parser.add_setting('-t', '--test', action='store_false'), expected_src.format(extra_imports='', typ='bool')),
-    (11, lambda parser: parser.add_setting('-t', '--test', action=settngs.BooleanOptionalAction), expected_src.format(extra_imports='', typ='bool')),
-    (12, lambda parser: parser.add_setting('-t', '--test', action=_customAction), expected_src.format(extra_imports='import typing\n', typ='typing.Any')),
-    (13, lambda parser: parser.add_setting('-t', '--test', action='help'), no_type_expected_src),
-    (14, lambda parser: parser.add_setting('-t', '--test', action='version'), no_type_expected_src),
-    (15, lambda parser: parser.add_setting('-t', '--test', type=int), expected_src.format(extra_imports='', typ='int')),
-    (16, lambda parser: parser.add_setting('-t', '--test', type=_typed_function), expected_src.format(extra_imports='import tests.settngs_test\n', typ='tests.settngs_test.test_type')),
-    (17, lambda parser: parser.add_setting('-t', '--test', type=_untyped_function, default=1), expected_src.format(extra_imports='', typ='int')),
-    (18, lambda parser: parser.add_setting('-t', '--test', type=_untyped_function), expected_src.format(extra_imports='import typing\n', typ='typing.Any')),
+    (0, lambda parser: parser.add_setting('-t', '--test'), TypeResult(extra_imports='', typ='str | None')),
+    (1, lambda parser: parser.add_setting('-t', '--test', cmdline=False), TypeResult(extra_imports='import typing\n', typ='typing.Any')),
+    (2, lambda parser: parser.add_setting('-t', '--test', default=1, file=True, cmdline=False), TypeResult(extra_imports='', typ='int')),
+    (3, lambda parser: parser.add_setting('-t', '--test', default='test'), TypeResult(extra_imports='', typ='str')),
+    (4, lambda parser: parser.add_setting('-t', '--test', default='test', file=True, cmdline=False), TypeResult(extra_imports='', typ='str')),
+    (5, lambda parser: parser.add_setting('-t', '--test', action='count'), TypeResult(extra_imports='', typ='int | None')),
+    (6, lambda parser: parser.add_setting('-t', '--test', action='append'), TypeResult(extra_imports='', typ=f'{List[str]} | None')),
+    (7, lambda parser: parser.add_setting('-t', '--test', action='extend'), TypeResult(extra_imports='', typ=f'{List[str]} | None')),
+    (8, lambda parser: parser.add_setting('-t', '--test', nargs='+'), TypeResult(extra_imports='', typ=f'{List[str]} | None')),
+    (9, lambda parser: parser.add_setting('-t', '--test', nargs='+', type=pathlib.Path), TypeResult(extra_imports='import pathlib._local\n' if sys.version_info[:2] == (3, 13) else 'import pathlib\n', typ=f'{List[pathlib.Path]} | None')),
+    (10, lambda parser: parser.add_setting('-t', '--test', nargs='+', type=test_enum), TypeResult(extra_imports='import tests.settngs_test\n', typ=f'{List[test_enum]} | None')),
+    (11, lambda parser: parser.add_setting('-t', '--test', action='store_const', const=1), TypeResult(extra_imports='', typ='int | None')),
+    (12, lambda parser: parser.add_setting('-t', '--test', action='append_const', const=1), TypeResult(extra_imports='', typ=f'{List[int]} | None')),
+    (13, lambda parser: parser.add_setting('-t', '--test', action='store_true'), TypeResult(extra_imports='', typ='bool')),
+    (14, lambda parser: parser.add_setting('-t', '--test', action='store_false'), TypeResult(extra_imports='', typ='bool')),
+    (15, lambda parser: parser.add_setting('-t', '--test', action=argparse.BooleanOptionalAction), TypeResult(extra_imports='', typ='bool | None')),
+    (16, lambda parser: parser.add_setting('-t', '--test', action=_customAction), TypeResult(extra_imports='import typing\n', typ='typing.Any')),
+    (17, lambda parser: parser.add_setting('-t', '--test', type=test_enum), TypeResult(extra_imports='import tests.settngs_test\n', typ='tests.settngs_test.test_enum | None')),
+    (18, lambda parser: parser.add_setting('-t', '--test', type=int), TypeResult(extra_imports='', typ='int | None')),
+    (19, lambda parser: parser.add_setting('-t', '--test', type=int, nargs='+'), TypeResult(extra_imports='', typ=f'{List[int]} | None')),
+    (20, lambda parser: parser.add_setting('-t', '--test', type=_typed_function), TypeResult(extra_imports='import tests.settngs_test\n', typ='tests.settngs_test.test_type | None')),
+    (21, lambda parser: parser.add_setting('-t', '--test', type=_untyped_function, default=1), TypeResult(extra_imports='', typ='int')),
+    (22, lambda parser: parser.add_setting('-t', '--test', type=_untyped_function, default=[1]), TypeResult(extra_imports='', typ=f'{List[int]}')),
+    (23, lambda parser: parser.add_setting('-t', '--test', type=_untyped_function), TypeResult(extra_imports='import typing\n', typ='typing.Any')),
+    (24, lambda parser: parser.add_setting('-t', '--test', type=_untyped_function, default={1}), TypeResult(extra_imports='', typ=f'{Set[int]}')),
+    (25, lambda parser: parser.add_setting('-t', '--test', action='append', type=int), TypeResult(extra_imports='', typ=f'{List[int]} | None')),
+    (26, lambda parser: parser.add_setting('-t', '--test', action='extend', type=int, nargs=2), TypeResult(extra_imports='', typ=f'{List[int]} | None')),
+    (27, lambda parser: parser.add_setting('-t', '--test', action='append', type=int, nargs=2), TypeResult(extra_imports='', typ=f'{List[List[int]]} | None')),
+    (28, lambda parser: parser.add_setting('-t', '--test', action='extend', nargs='+'), TypeResult(extra_imports='', typ=f'{List[str]} | None')),
+    (29, lambda parser: parser.add_setting('-t', '--test', action='extend', type=_typed_list_generic_function), TypeResult(extra_imports='import tests.settngs_test\n', typ=f'{List[test_type]} | None')),
+    (30, lambda parser: parser.add_setting('-t', '--test', action='extend', type=_typed_list_function), TypeResult(extra_imports='', typ=f'{settngs._type_to_string(List)[0]} | None')),
+    (31, lambda parser: parser.add_setting('-t', '--test', action='extend', type=_typed_set_function), TypeResult(extra_imports='', typ=f'{settngs._type_to_string(Set)[0]} | None')),
 )
 
 
@@ -723,14 +763,13 @@ def test_generate_ns(settngs_manager, num, set_options, expected):
     imports, types = settngs_manager.generate_ns()
     generated_src = '\n\n\n'.join((imports, types))
 
-    assert generated_src == expected
+    assert generated_src == expected_src.format(**expected._asdict())
 
     ast.parse(generated_src)
 
 
 expected_src_dict = '''from __future__ import annotations
 
-import typing
 {extra_imports}
 
 class test(typing.TypedDict):
@@ -740,49 +779,18 @@ class test(typing.TypedDict):
 class SettngsDict(typing.TypedDict):
     test: test
 '''
-no_type_expected_src_dict = '''from __future__ import annotations
-
-import typing
 
 
-class test(typing.TypedDict):
-    ...
-
-
-class SettngsDict(typing.TypedDict):
-    test: test
-'''
-settings_dict = (
-    (0, lambda parser: parser.add_setting('-t', '--test'), expected_src_dict.format(extra_imports='', typ='str')),
-    (1, lambda parser: parser.add_setting('-t', '--test', cmdline=False), expected_src_dict.format(extra_imports='', typ='typing.Any')),
-    (2, lambda parser: parser.add_setting('-t', '--test', default=1, file=True, cmdline=False), expected_src_dict.format(extra_imports='', typ='int')),
-    (3, lambda parser: parser.add_setting('-t', '--test', action='count'), expected_src_dict.format(extra_imports='', typ='int')),
-    (4, lambda parser: parser.add_setting('-t', '--test', action='append'), expected_src_dict.format(extra_imports='' if sys.version_info < (3, 9) else '', typ='typing.List[str]' if sys.version_info < (3, 9) else 'list[str]')),
-    (5, lambda parser: parser.add_setting('-t', '--test', action='extend'), expected_src_dict.format(extra_imports='' if sys.version_info < (3, 9) else '', typ='typing.List[str]' if sys.version_info < (3, 9) else 'list[str]')),
-    (6, lambda parser: parser.add_setting('-t', '--test', nargs='+'), expected_src_dict.format(extra_imports='' if sys.version_info < (3, 9) else '', typ='typing.List[str]' if sys.version_info < (3, 9) else 'list[str]')),
-    (7, lambda parser: parser.add_setting('-t', '--test', action='store_const', const=1), expected_src_dict.format(extra_imports='', typ='int')),
-    (8, lambda parser: parser.add_setting('-t', '--test', action='append_const', const=1), expected_src_dict.format(extra_imports='', typ='list')),
-    (9, lambda parser: parser.add_setting('-t', '--test', action='store_true'), expected_src_dict.format(extra_imports='', typ='bool')),
-    (10, lambda parser: parser.add_setting('-t', '--test', action='store_false'), expected_src_dict.format(extra_imports='', typ='bool')),
-    (11, lambda parser: parser.add_setting('-t', '--test', action=settngs.BooleanOptionalAction), expected_src_dict.format(extra_imports='', typ='bool')),
-    (12, lambda parser: parser.add_setting('-t', '--test', action=_customAction), expected_src_dict.format(extra_imports='', typ='typing.Any')),
-    (13, lambda parser: parser.add_setting('-t', '--test', action='help'), no_type_expected_src_dict),
-    (14, lambda parser: parser.add_setting('-t', '--test', action='version'), no_type_expected_src_dict),
-    (15, lambda parser: parser.add_setting('-t', '--test', type=int), expected_src_dict.format(extra_imports='', typ='int')),
-    (16, lambda parser: parser.add_setting('-t', '--test', type=_typed_function), expected_src_dict.format(extra_imports='import tests.settngs_test\n', typ='tests.settngs_test.test_type')),
-    (17, lambda parser: parser.add_setting('-t', '--test', type=_untyped_function, default=1), expected_src_dict.format(extra_imports='', typ='int')),
-    (18, lambda parser: parser.add_setting('-t', '--test', type=_untyped_function), expected_src_dict.format(extra_imports='', typ='typing.Any')),
-)
-
-
-@pytest.mark.parametrize('num,set_options,expected', settings_dict)
+@pytest.mark.parametrize('num,set_options,expected', settings)
 def test_generate_dict(settngs_manager, num, set_options, expected):
     settngs_manager.add_group('test', set_options)
 
     imports, types = settngs_manager.generate_dict()
     generated_src = '\n\n\n'.join((imports, types))
 
-    assert generated_src == expected
+    if 'import typing' not in expected.extra_imports:
+        expected = TypeResult('import typing\n' + expected.extra_imports, expected.typ)
+    assert generated_src == expected_src_dict.format(**expected._asdict())
 
     ast.parse(generated_src)