Use PEP 604 syntax wherever possible, part II (#7514)

Co-authored-by: Jelle Zijlstra <jelle.zijlstra@gmail.com>

stdlib/@python2/calendar.pyi

@@ -1,8 +1,8 @@
 import datetime
 from time import struct_time
-from typing import Any, Iterable, Optional, Sequence
+from typing import Any, Iterable, Sequence
 
-_LocaleType = tuple[Optional[str], Optional[str]]
+_LocaleType = tuple[str | None, str | None]
 
 class IllegalMonthError(ValueError):
     def __init__(self, month: int) -> None: ...

stdlib/@python2/copy_reg.pyi

@@ -1,7 +1,7 @@
-from typing import Any, Callable, Hashable, Optional, SupportsInt, TypeVar, Union
+from typing import Any, Callable, Hashable, SupportsInt, TypeVar, Union
 
 _TypeT = TypeVar("_TypeT", bound=type)
-_Reduce = Union[tuple[Callable[..., _TypeT], tuple[Any, ...]], tuple[Callable[..., _TypeT], tuple[Any, ...], Optional[Any]]]
+_Reduce = Union[tuple[Callable[..., _TypeT], tuple[Any, ...]], tuple[Callable[..., _TypeT], tuple[Any, ...], Any | None]]
 
 __all__ = ["pickle", "constructor", "add_extension", "remove_extension", "clear_extension_cache"]
 

stdlib/@python2/copyreg.pyi

@@ -1,7 +1,7 @@
-from typing import Any, Callable, Hashable, Optional, SupportsInt, TypeVar, Union
+from typing import Any, Callable, Hashable, SupportsInt, TypeVar, Union
 
 _TypeT = TypeVar("_TypeT", bound=type)
-_Reduce = Union[tuple[Callable[..., _TypeT], tuple[Any, ...]], tuple[Callable[..., _TypeT], tuple[Any, ...], Optional[Any]]]
+_Reduce = Union[tuple[Callable[..., _TypeT], tuple[Any, ...]], tuple[Callable[..., _TypeT], tuple[Any, ...], Any | None]]
 
 __all__ = ["pickle", "constructor", "add_extension", "remove_extension", "clear_extension_cache"]
 

stdlib/@python2/ctypes/__init__.pyi

@@ -9,7 +9,6 @@ from typing import (
     Iterable,
     Iterator,
     Mapping,
-    Optional,
     Sequence,
     Text,
     TypeVar,
@@ -88,7 +87,7 @@ class _CData(metaclass=_CDataMeta):
 class _CanCastTo(_CData): ...
 class _PointerLike(_CanCastTo): ...
 
-_ECT = Callable[[Optional[type[_CData]], _FuncPointer, tuple[_CData, ...]], _CData]
+_ECT = Callable[[type[_CData] | None, _FuncPointer, tuple[_CData, ...]], _CData]
 _PF = _UnionT[tuple[int], tuple[int, str], tuple[int, str, Any]]
 
 class _FuncPointer(_PointerLike, _CData):

stdlib/@python2/distutils/ccompiler.pyi

@@ -1,6 +1,6 @@
-from typing import Any, Callable, Optional, Union
+from typing import Any, Callable, Union
 
-_Macro = Union[tuple[str], tuple[str, Optional[str]]]
+_Macro = Union[tuple[str], tuple[str, str | None]]
 
 def gen_lib_options(
     compiler: CCompiler, library_dirs: list[str], runtime_library_dirs: list[str], libraries: list[str]

stdlib/@python2/distutils/fancy_getopt.pyi

@@ -1,6 +1,6 @@
-from typing import Any, Mapping, Optional, overload
+from typing import Any, Mapping, overload
 
-_Option = tuple[str, Optional[str], str]
+_Option = tuple[str, str | None, str]
 _GR = tuple[list[str], OptionDummy]
 
 def fancy_getopt(

stdlib/@python2/email/mime/application.pyi

@@ -1,7 +1,7 @@
 from email.mime.nonmultipart import MIMENonMultipart
-from typing import Callable, Optional, Union
+from typing import Callable, Union
 
-_ParamsType = Union[str, None, tuple[str, Optional[str], str]]
+_ParamsType = Union[str, None, tuple[str, str | None, str]]
 
 class MIMEApplication(MIMENonMultipart):
     def __init__(

stdlib/@python2/imaplib.pyi

@@ -3,14 +3,14 @@ import time
 from builtins import list as List  # alias to avoid name clashes with `IMAP4.list`
 from socket import socket as _socket
 from ssl import SSLSocket
-from typing import IO, Any, Callable, Pattern, Text, Union
+from typing import IO, Any, Callable, Pattern, Text
 from typing_extensions import Literal
 
 # TODO: Commands should use their actual return types, not this type alias.
 #       E.g. tuple[Literal["OK"], list[bytes]]
 _CommandResults = tuple[str, list[Any]]
 
-_AnyResponseData = Union[list[None], list[Union[bytes, tuple[bytes, bytes]]]]
+_AnyResponseData = list[None] | list[bytes | tuple[bytes, bytes]]
 
 class IMAP4:
     error: type[Exception] = ...

stdlib/@python2/inspect.pyi

@@ -1,5 +1,5 @@
 from types import CodeType, FrameType, FunctionType, MethodType, ModuleType, TracebackType
-from typing import Any, AnyStr, Callable, NamedTuple, Optional, Sequence, Union
+from typing import Any, AnyStr, Callable, NamedTuple, Sequence, Union
 
 # Types and members
 class EndOfBlock(Exception): ...
@@ -106,7 +106,7 @@ class Traceback(NamedTuple):
     code_context: list[str] | None
     index: int | None  # type: ignore[assignment]
 
-_FrameInfo = tuple[FrameType, str, int, str, Optional[list[str]], Optional[int]]
+_FrameInfo = tuple[FrameType, str, int, str, list[str] | None, int | None]
 
 def getouterframes(frame: FrameType, context: int = ...) -> list[_FrameInfo]: ...
 def getframeinfo(frame: FrameType | TracebackType, context: int = ...) -> Traceback: ...

stdlib/@python2/lib2to3/pgen2/grammar.pyi

@@ -1,7 +1,7 @@
 from _typeshed import Self, StrPath
-from typing import Optional, Text
+from typing import Text
 
-_Label = tuple[int, Optional[Text]]
+_Label = tuple[int, Text | None]
 _DFA = list[list[tuple[int, int]]]
 _DFAS = tuple[_DFA, dict[int, int]]
 

stdlib/@python2/lib2to3/pytree.pyi

@@ -1,12 +1,12 @@
 from _typeshed import Self
 from lib2to3.pgen2.grammar import Grammar
-from typing import Any, Callable, Iterator, Optional, Text, TypeVar
+from typing import Any, Callable, Iterator, Text, TypeVar
 
 _P = TypeVar("_P")
 _NL = Node | Leaf
 _Context = tuple[Text, int, int]
 _Results = dict[Text, _NL]
-_RawNode = tuple[int, Text, _Context, Optional[list[_NL]]]
+_RawNode = tuple[int, Text, _Context, list[_NL] | None]
 _Convert = Callable[[Grammar, _RawNode], Any]
 
 HUGE: int

stdlib/@python2/logging/__init__.pyi

@@ -2,9 +2,9 @@ import threading
 from _typeshed import StrPath, SupportsWrite
 from time import struct_time
 from types import FrameType, TracebackType
-from typing import IO, Any, Callable, Generic, Mapping, MutableMapping, Optional, Sequence, Text, TypeVar, Union, overload
+from typing import IO, Any, Callable, Generic, Mapping, MutableMapping, Sequence, Text, TypeVar, Union, overload
 
-_SysExcInfoType = Union[tuple[type, BaseException, Optional[TracebackType]], tuple[None, None, None]]
+_SysExcInfoType = Union[tuple[type, BaseException, TracebackType | None], tuple[None, None, None]]
 _ExcInfoType = None | bool | _SysExcInfoType
 _ArgsType = Union[tuple[Any, ...], Mapping[str, Any]]
 _FilterType = Filter | Callable[[LogRecord], int]

stdlib/@python2/msilib/sequence.pyi

@@ -1,9 +1,8 @@
 import sys
-from typing import Optional
 
 if sys.platform == "win32":
 
-    _SequenceType = list[tuple[str, Optional[str], int]]
+    _SequenceType = list[tuple[str, str | None, int]]
 
     AdminExecuteSequence: _SequenceType
     AdminUISequence: _SequenceType

stdlib/@python2/netrc.pyi

@@ -1,4 +1,4 @@
-from typing import Optional, Text
+from typing import Text
 
 class NetrcParseError(Exception):
     filename: str | None
@@ -7,7 +7,7 @@ class NetrcParseError(Exception):
     def __init__(self, msg: str, filename: Text | None = ..., lineno: int | None = ...) -> None: ...
 
 # (login, account, password) tuple
-_NetrcTuple = tuple[str, Optional[str], Optional[str]]
+_NetrcTuple = tuple[str, str | None, str | None]
 
 class netrc:
     hosts: dict[str, _NetrcTuple]

stdlib/@python2/os/__init__.pyi

@@ -16,7 +16,6 @@ from typing import (
     Sequence,
     Text,
     TypeVar,
-    Union,
     overload,
 )
 
@@ -269,7 +268,7 @@ def execlpe(file: Text, __arg0: bytes | Text, *args: Any) -> NoReturn: ...
 
 # The docs say `args: tuple or list of strings`
 # The implementation enforces tuple or list so we can't use Sequence.
-_ExecVArgs = Union[tuple[Union[bytes, Text], ...], list[bytes], list[Text], list[Union[bytes, Text]]]
+_ExecVArgs = tuple[bytes | Text, ...] | list[bytes] | list[Text] | list[bytes | Text]
 
 def execv(path: Text, args: _ExecVArgs) -> NoReturn: ...
 def execve(path: Text, args: _ExecVArgs, env: Mapping[str, str]) -> NoReturn: ...

stdlib/@python2/pickle.pyi

@@ -1,4 +1,4 @@
-from typing import IO, Any, Callable, Iterator, Optional, Union
+from typing import IO, Any, Callable, Iterator, Union
 
 HIGHEST_PROTOCOL: int
 bytes_types: tuple[type[Any], ...]  # undocumented
@@ -16,8 +16,8 @@ _reducedtype = Union[
     str,
     tuple[Callable[..., Any], tuple[Any, ...]],
     tuple[Callable[..., Any], tuple[Any, ...], Any],
-    tuple[Callable[..., Any], tuple[Any, ...], Any, Optional[Iterator[Any]]],
-    tuple[Callable[..., Any], tuple[Any, ...], Any, Optional[Iterator[Any]], Optional[Iterator[Any]]],
+    tuple[Callable[..., Any], tuple[Any, ...], Any, Iterator[Any] | None],
+    tuple[Callable[..., Any], tuple[Any, ...], Any, Iterator[Any] | None, Iterator[Any] | None],
 ]
 
 class Pickler:

stdlib/@python2/pkgutil.pyi

@@ -1,12 +1,12 @@
 from _typeshed import SupportsRead
-from typing import IO, Any, Callable, Iterable, Iterator, TypeVar, Union
+from typing import IO, Any, Callable, Iterable, Iterator, TypeVar
 
 Loader = Any
 MetaPathFinder = Any
 PathEntryFinder = Any
 
 _PathT = TypeVar("_PathT", bound=Iterable[str])
-_ModuleInfoLike = tuple[Union[MetaPathFinder, PathEntryFinder], str, bool]
+_ModuleInfoLike = tuple[MetaPathFinder | PathEntryFinder, str, bool]
 
 def extend_path(path: _PathT, name: str) -> _PathT: ...
 

stdlib/@python2/pyexpat/__init__.pyi

@@ -1,7 +1,7 @@
 import pyexpat.errors as errors
 import pyexpat.model as model
 from _typeshed import SupportsRead
-from typing import Any, Callable, Optional, Text
+from typing import Any, Callable, Text
 
 EXPAT_VERSION: str  # undocumented
 version_info: tuple[int, int, int]  # undocumented
@@ -19,7 +19,7 @@ XML_PARAM_ENTITY_PARSING_NEVER: int
 XML_PARAM_ENTITY_PARSING_UNLESS_STANDALONE: int
 XML_PARAM_ENTITY_PARSING_ALWAYS: int
 
-_Model = tuple[int, int, Optional[str], tuple[Any, ...]]
+_Model = tuple[int, int, str | None, tuple[Any, ...]]
 
 class XMLParserType(object):
     def Parse(self, __data: Text | bytes, __isfinal: bool = ...) -> int: ...

stdlib/@python2/sndhdr.pyi

@@ -1,6 +1,6 @@
-from typing import Text, Union
+from typing import Text
 
-_SndHeaders = tuple[str, int, int, int, Union[int, str]]
+_SndHeaders = tuple[str, int, int, int, int | str]
 
 def what(filename: Text) -> _SndHeaders | None: ...
 def whathdr(filename: Text) -> _SndHeaders | None: ...

stdlib/@python2/socket.pyi

@@ -1,5 +1,5 @@
 import sys
-from typing import Any, BinaryIO, Iterable, Text, Union, overload
+from typing import Any, BinaryIO, Iterable, Text, overload
 
 # ----- Constants -----
 # Some socket families are listed in the "Socket families" section of the docs,
@@ -373,7 +373,7 @@ class timeout(error):
 
 # Addresses can be either tuples of varying lengths (AF_INET, AF_INET6,
 # AF_NETLINK, AF_TIPC) or strings (AF_UNIX).
-_Address = Union[tuple[Any, ...], str]
+_Address = tuple[Any, ...] | str
 _RetAddress = Any
 # TODO Most methods allow bytes as address objects
 

stdlib/@python2/sre_parse.pyi

@@ -1,4 +1,4 @@
-from typing import Any, Iterable, Match, Optional, Pattern as _Pattern
+from typing import Any, Iterable, Match, Pattern as _Pattern
 
 SPECIAL_CHARS: str
 REPEAT_CHARS: str
@@ -21,7 +21,7 @@ class Pattern:
     def closegroup(self, gid: int) -> None: ...
     def checkgroup(self, gid: int) -> bool: ...
 
-_OpSubpatternType = tuple[Optional[int], int, int, SubPattern]
+_OpSubpatternType = tuple[int | None, int, int, SubPattern]
 _OpGroupRefExistsType = tuple[int, SubPattern, SubPattern]
 _OpInType = list[tuple[str, int]]
 _OpBranchType = tuple[None, list[SubPattern]]
@@ -56,7 +56,7 @@ def isdigit(char: str) -> bool: ...
 def isname(name: str) -> bool: ...
 def parse(str: str, flags: int = ..., pattern: Pattern = ...) -> SubPattern: ...
 
-_Template = tuple[list[tuple[int, int]], list[Optional[int]]]
+_Template = tuple[list[tuple[int, int]], list[int | None]]
 
 def parse_template(source: str, pattern: _Pattern[Any]) -> _Template: ...
 def expand_template(template: _Template, match: Match[Any]) -> str: ...

stdlib/@python2/trace.pyi

@@ -1,12 +1,12 @@
 import types
 from _typeshed import StrPath
-from typing import Any, Callable, Mapping, Optional, Sequence, TypeVar
+from typing import Any, Callable, Mapping, Sequence, TypeVar
 from typing_extensions import ParamSpec
 
 _T = TypeVar("_T")
 _P = ParamSpec("_P")
 _localtrace = Callable[[types.FrameType, str, Any], Callable[..., Any]]
-_fileModuleFunction = tuple[str, Optional[str], str]
+_fileModuleFunction = tuple[str, str | None, str]
 
 class CoverageResults:
     def __init__(

stdlib/@python2/traceback.pyi

@@ -1,7 +1,7 @@
 from types import FrameType, TracebackType
-from typing import IO, Optional
+from typing import IO
 
-_PT = tuple[str, int, str, Optional[str]]
+_PT = tuple[str, int, str, str | None]
 
 def print_tb(tb: TracebackType | None, limit: int | None = ..., file: IO[str] | None = ...) -> None: ...
 def print_exception(

stdlib/_socket.pyi

@@ -1,7 +1,7 @@
 import sys
 from _typeshed import ReadableBuffer, WriteableBuffer
 from collections.abc import Iterable
-from typing import Any, SupportsInt, Union, overload
+from typing import Any, SupportsInt, overload
 
 if sys.version_info >= (3, 8):
     from typing import SupportsIndex
@@ -15,7 +15,7 @@ _CMSGArg = tuple[int, int, ReadableBuffer]
 
 # Addresses can be either tuples of varying lengths (AF_INET, AF_INET6,
 # AF_NETLINK, AF_TIPC) or strings (AF_UNIX).
-_Address = Union[tuple[Any, ...], str]
+_Address = tuple[Any, ...] | str
 _RetAddress = Any
 # TODO Most methods allow bytes as address objects
 

stdlib/_thread.pyi

@@ -2,7 +2,7 @@ import sys
 from _typeshed import structseq
 from threading import Thread
 from types import TracebackType
-from typing import Any, Callable, NoReturn, Optional
+from typing import Any, Callable, NoReturn
 from typing_extensions import final
 
 error = RuntimeError
@@ -33,9 +33,7 @@ TIMEOUT_MAX: float
 if sys.version_info >= (3, 8):
     def get_native_id() -> int: ...  # only available on some platforms
     @final
-    class _ExceptHookArgs(
-        structseq[Any], tuple[type[BaseException], Optional[BaseException], Optional[TracebackType], Optional[Thread]]
-    ):
+    class _ExceptHookArgs(structseq[Any], tuple[type[BaseException], BaseException | None, TracebackType | None, Thread | None]):
         @property
         def exc_type(self) -> type[BaseException]: ...
         @property

stdlib/calendar.pyi

@@ -1,7 +1,7 @@
 import datetime
 import sys
 from time import struct_time
-from typing import Any, Iterable, Optional, Sequence
+from typing import Any, Iterable, Sequence
 from typing_extensions import Literal
 
 __all__ = [
@@ -31,7 +31,7 @@ __all__ = [
     "weekheader",
 ]
 
-_LocaleType = tuple[Optional[str], Optional[str]]
+_LocaleType = tuple[str | None, str | None]
 
 class IllegalMonthError(ValueError):
     def __init__(self, month: int) -> None: ...

stdlib/cgitb.pyi

@@ -1,8 +1,8 @@
 from _typeshed import StrOrBytesPath
 from types import FrameType, TracebackType
-from typing import IO, Any, Callable, Optional
+from typing import IO, Any, Callable
 
-_ExcInfo = tuple[Optional[type[BaseException]], Optional[BaseException], Optional[TracebackType]]
+_ExcInfo = tuple[type[BaseException] | None, BaseException | None, TracebackType | None]
 
 __UNDEF__: object  # undocumented sentinel
 

stdlib/copyreg.pyi

@@ -1,7 +1,7 @@
-from typing import Any, Callable, Hashable, Optional, SupportsInt, TypeVar, Union
+from typing import Any, Callable, Hashable, SupportsInt, TypeVar, Union
 
 _T = TypeVar("_T")
-_Reduce = Union[tuple[Callable[..., _T], tuple[Any, ...]], tuple[Callable[..., _T], tuple[Any, ...], Optional[Any]]]
+_Reduce = Union[tuple[Callable[..., _T], tuple[Any, ...]], tuple[Callable[..., _T], tuple[Any, ...], Any | None]]
 
 __all__ = ["pickle", "constructor", "add_extension", "remove_extension", "clear_extension_cache"]
 

stdlib/ctypes/__init__.pyi

@@ -1,20 +1,7 @@
 import sys
 from _typeshed import ReadableBuffer, Self, WriteableBuffer
 from abc import abstractmethod
-from typing import (
-    Any,
-    Callable,
-    ClassVar,
-    Generic,
-    Iterable,
-    Iterator,
-    Mapping,
-    Optional,
-    Sequence,
-    TypeVar,
-    Union as _UnionT,
-    overload,
-)
+from typing import Any, Callable, ClassVar, Generic, Iterable, Iterator, Mapping, Sequence, TypeVar, Union as _UnionT, overload
 
 if sys.version_info >= (3, 9):
     from types import GenericAlias
@@ -97,7 +84,7 @@ class _CData(metaclass=_CDataMeta):
 class _CanCastTo(_CData): ...
 class _PointerLike(_CanCastTo): ...
 
-_ECT = Callable[[Optional[type[_CData]], _FuncPointer, tuple[_CData, ...]], _CData]
+_ECT = Callable[[type[_CData] | None, _FuncPointer, tuple[_CData, ...]], _CData]
 _PF = _UnionT[tuple[int], tuple[int, str], tuple[int, str, Any]]
 
 class _FuncPointer(_PointerLike, _CData):

stdlib/distutils/ccompiler.pyi

@@ -1,6 +1,6 @@
-from typing import Any, Callable, Optional, Union
+from typing import Any, Callable, Union
 
-_Macro = Union[tuple[str], tuple[str, Optional[str]]]
+_Macro = Union[tuple[str], tuple[str, str | None]]
 
 def gen_lib_options(
     compiler: CCompiler, library_dirs: list[str], runtime_library_dirs: list[str], libraries: list[str]

stdlib/distutils/fancy_getopt.pyi

@@ -1,6 +1,6 @@
-from typing import Any, Iterable, Mapping, Optional, overload
+from typing import Any, Iterable, Mapping, overload
 
-_Option = tuple[str, Optional[str], str]
+_Option = tuple[str, str | None, str]
 _GR = tuple[list[str], OptionDummy]
 
 def fancy_getopt(

stdlib/email/message.pyi

@@ -4,7 +4,7 @@ from email.errors import MessageDefect
 from email.policy import Policy
 
 # using a type alias ("_HeaderType = Any") breaks mypy, who knows why
-from typing import Any, Any as _HeaderType, Generator, Iterator, Optional, Sequence, TypeVar, Union
+from typing import Any, Any as _HeaderType, Generator, Iterator, Sequence, TypeVar, Union
 
 __all__ = ["Message", "EmailMessage"]
 
@@ -12,8 +12,8 @@ _T = TypeVar("_T")
 
 _PayloadType = list[Message] | str | bytes
 _CharsetType = Charset | str | None
-_ParamsType = Union[str, None, tuple[str, Optional[str], str]]
-_ParamType = Union[str, tuple[Optional[str], Optional[str], str]]
+_ParamsType = Union[str, None, tuple[str, str | None, str]]
+_ParamType = Union[str, tuple[str | None, str | None, str]]
 
 class Message:
     policy: Policy  # undocumented

stdlib/email/mime/application.pyi

@@ -1,10 +1,10 @@
 from email.mime.nonmultipart import MIMENonMultipart
 from email.policy import Policy
-from typing import Callable, Optional, Union
+from typing import Callable, Union
 
 __all__ = ["MIMEApplication"]
 
-_ParamsType = Union[str, None, tuple[str, Optional[str], str]]
+_ParamsType = Union[str, None, tuple[str, str | None, str]]
 
 class MIMEApplication(MIMENonMultipart):
     def __init__(

stdlib/email/mime/audio.pyi

@@ -1,10 +1,10 @@
 from email.mime.nonmultipart import MIMENonMultipart
 from email.policy import Policy
-from typing import Callable, Optional, Union
+from typing import Callable, Union
 
 __all__ = ["MIMEAudio"]
 
-_ParamsType = Union[str, None, tuple[str, Optional[str], str]]
+_ParamsType = Union[str, None, tuple[str, str | None, str]]
 
 class MIMEAudio(MIMENonMultipart):
     def __init__(

stdlib/email/mime/base.pyi

@@ -1,10 +1,10 @@
 import email.message
 from email.policy import Policy
-from typing import Optional, Union
+from typing import Union
 
 __all__ = ["MIMEBase"]
 
-_ParamsType = Union[str, None, tuple[str, Optional[str], str]]
+_ParamsType = Union[str, None, tuple[str, str | None, str]]
 
 class MIMEBase(email.message.Message):
     def __init__(self, _maintype: str, _subtype: str, *, policy: Policy | None = ..., **_params: _ParamsType) -> None: ...

stdlib/email/mime/image.pyi

@@ -1,10 +1,10 @@
 from email.mime.nonmultipart import MIMENonMultipart
 from email.policy import Policy
-from typing import Callable, Optional, Union
+from typing import Callable, Union
 
 __all__ = ["MIMEImage"]
 
-_ParamsType = Union[str, None, tuple[str, Optional[str], str]]
+_ParamsType = Union[str, None, tuple[str, str | None, str]]
 
 class MIMEImage(MIMENonMultipart):
     def __init__(

stdlib/email/mime/multipart.pyi

@@ -1,11 +1,11 @@
 from email.message import Message
 from email.mime.base import MIMEBase
 from email.policy import Policy
-from typing import Optional, Sequence, Union
+from typing import Sequence, Union
 
 __all__ = ["MIMEMultipart"]
 
-_ParamsType = Union[str, None, tuple[str, Optional[str], str]]
+_ParamsType = Union[str, None, tuple[str, str | None, str]]
 
 class MIMEMultipart(MIMEBase):
     def __init__(

stdlib/email/utils.pyi

@@ -1,7 +1,7 @@
 import datetime
 import sys
 from email.charset import Charset
-from typing import Optional, Union, overload
+from typing import Union, overload
 
 __all__ = [
     "collapse_rfc2231_value",
@@ -21,8 +21,8 @@ __all__ = [
     "unquote",
 ]
 
-_ParamType = Union[str, tuple[Optional[str], Optional[str], str]]
-_PDTZ = tuple[int, int, int, int, int, int, int, int, int, Optional[int]]
+_ParamType = Union[str, tuple[str | None, str | None, str]]
+_PDTZ = tuple[int, int, int, int, int, int, int, int, int, int | None]
 
 def quote(str: str) -> str: ...
 def unquote(str: str) -> str: ...

stdlib/grp.pyi

@@ -1,11 +1,11 @@
 import sys
 from _typeshed import structseq
-from typing import Any, Optional
+from typing import Any
 from typing_extensions import final
 
 if sys.platform != "win32":
     @final
-    class struct_group(structseq[Any], tuple[str, Optional[str], int, list[str]]):
+    class struct_group(structseq[Any], tuple[str, str | None, int, list[str]]):
         @property
         def gr_name(self) -> str: ...
         @property

stdlib/imaplib.pyi

@@ -5,7 +5,7 @@ from _typeshed import Self
 from socket import socket as _socket
 from ssl import SSLContext, SSLSocket
 from types import TracebackType
-from typing import IO, Any, Callable, Pattern, Union
+from typing import IO, Any, Callable, Pattern
 from typing_extensions import Literal
 
 __all__ = ["IMAP4", "IMAP4_stream", "Internaldate2tuple", "Int2AP", "ParseFlags", "Time2Internaldate", "IMAP4_SSL"]
@@ -14,7 +14,7 @@ __all__ = ["IMAP4", "IMAP4_stream", "Internaldate2tuple", "Int2AP", "ParseFlags"
 #       E.g. Tuple[Literal["OK"], List[bytes]]
 _CommandResults = tuple[str, list[Any]]
 
-_AnyResponseData = Union[list[None], list[Union[bytes, tuple[bytes, bytes]]]]
+_AnyResponseData = list[None] | list[bytes | tuple[bytes, bytes]]
 
 _list = list  # conflicts with a method named "list"
 

stdlib/lib2to3/pgen2/grammar.pyi

@@ -1,7 +1,6 @@
 from _typeshed import Self, StrPath
-from typing import Optional
 
-_Label = tuple[int, Optional[str]]
+_Label = tuple[int, str | None]
 _DFA = list[list[tuple[int, int]]]
 _DFAS = tuple[_DFA, dict[int, int]]
 

stdlib/lib2to3/pytree.pyi

@@ -1,11 +1,11 @@
 from _typeshed import Self
 from lib2to3.pgen2.grammar import Grammar
-from typing import Any, Callable, Iterator, Optional
+from typing import Any, Callable, Iterator
 
 _NL = Node | Leaf
 _Context = tuple[str, int, int]
 _Results = dict[str, _NL]
-_RawNode = tuple[int, str, _Context, Optional[list[_NL]]]
+_RawNode = tuple[int, str, _Context, list[_NL] | None]
 _Convert = Callable[[Grammar, _RawNode], Any]
 
 HUGE: int

stdlib/logging/__init__.pyi

@@ -6,7 +6,7 @@ from io import TextIOWrapper
 from string import Template
 from time import struct_time
 from types import FrameType, TracebackType
-from typing import Any, ClassVar, Generic, Optional, Pattern, TextIO, TypeVar, Union, overload
+from typing import Any, ClassVar, Generic, Pattern, TextIO, TypeVar, Union, overload
 from typing_extensions import Literal
 
 __all__ = [
@@ -54,9 +54,9 @@ __all__ = [
     "raiseExceptions",
 ]
 
-_SysExcInfoType = Union[tuple[type[BaseException], BaseException, Optional[TracebackType]], tuple[None, None, None]]
+_SysExcInfoType = Union[tuple[type[BaseException], BaseException, TracebackType | None], tuple[None, None, None]]
 _ExcInfoType = None | bool | _SysExcInfoType | BaseException
-_ArgsType = Union[tuple[object, ...], Mapping[str, object]]
+_ArgsType = tuple[object, ...] | Mapping[str, object]
 _FilterType = Filter | Callable[[LogRecord], int]
 _Level = int | str
 _FormatStyle = Literal["%", "{", "$"]

stdlib/msilib/sequence.pyi

@@ -1,9 +1,8 @@
 import sys
-from typing import Optional
 
 if sys.platform == "win32":
 
-    _SequenceType = list[tuple[str, Optional[str], int]]
+    _SequenceType = list[tuple[str, str | None, int]]
 
     AdminExecuteSequence: _SequenceType
     AdminUISequence: _SequenceType

stdlib/netrc.pyi

@@ -1,5 +1,4 @@
 from _typeshed import StrOrBytesPath
-from typing import Optional
 
 __all__ = ["netrc", "NetrcParseError"]
 
@@ -10,7 +9,7 @@ class NetrcParseError(Exception):
     def __init__(self, msg: str, filename: StrOrBytesPath | None = ..., lineno: int | None = ...) -> None: ...
 
 # (login, account, password) tuple
-_NetrcTuple = tuple[str, Optional[str], Optional[str]]
+_NetrcTuple = tuple[str, str | None, str | None]
 
 class netrc:
     hosts: dict[str, _NetrcTuple]

stdlib/pickle.pyi

@@ -1,5 +1,5 @@
 import sys
-from typing import Any, Callable, ClassVar, Iterable, Iterator, Mapping, Optional, Protocol, Union
+from typing import Any, Callable, ClassVar, Iterable, Iterator, Mapping, Protocol, Union
 from typing_extensions import final
 
 if sys.version_info >= (3, 8):
@@ -227,8 +227,8 @@ _reducedtype = Union[
     str,
     tuple[Callable[..., Any], tuple[Any, ...]],
     tuple[Callable[..., Any], tuple[Any, ...], Any],
-    tuple[Callable[..., Any], tuple[Any, ...], Any, Optional[Iterator[Any]]],
-    tuple[Callable[..., Any], tuple[Any, ...], Any, Optional[Iterator[Any]], Optional[Iterator[Any]]],
+    tuple[Callable[..., Any], tuple[Any, ...], Any, Iterator[Any] | None],
+    tuple[Callable[..., Any], tuple[Any, ...], Any, Iterator[Any] | None, Iterator[Any] | None],
 ]
 
 class Pickler:

stdlib/pyexpat/__init__.pyi

@@ -1,7 +1,7 @@
 import pyexpat.errors as errors
 import pyexpat.model as model
 from _typeshed import SupportsRead
-from typing import Any, Callable, Optional
+from typing import Any, Callable
 from typing_extensions import final
 
 EXPAT_VERSION: str  # undocumented
@@ -20,7 +20,7 @@ XML_PARAM_ENTITY_PARSING_NEVER: int
 XML_PARAM_ENTITY_PARSING_UNLESS_STANDALONE: int
 XML_PARAM_ENTITY_PARSING_ALWAYS: int
 
-_Model = tuple[int, int, Optional[str], tuple[Any, ...]]
+_Model = tuple[int, int, str | None, tuple[Any, ...]]
 
 @final
 class XMLParserType:

stdlib/smtplib.pyi

@@ -4,7 +4,7 @@ from email.message import Message as _Message
 from socket import socket
 from ssl import SSLContext
 from types import TracebackType
-from typing import Any, Pattern, Protocol, Sequence, Union, overload
+from typing import Any, Pattern, Protocol, Sequence, overload
 
 if sys.version_info >= (3, 7):
     __all__ = [
@@ -43,7 +43,7 @@ else:
 _Reply = tuple[int, bytes]
 _SendErrs = dict[str, _Reply]
 # Should match source_address for socket.create_connection
-_SourceAddress = tuple[Union[bytearray, bytes, str], int]
+_SourceAddress = tuple[bytearray | bytes | str, int]
 
 SMTP_PORT: int
 SMTP_SSL_PORT: int

stdlib/sre_parse.pyi

@@ -1,7 +1,7 @@
 import sys
 from sre_constants import *
 from sre_constants import _NamedIntConstant as _NIC, error as _Error
-from typing import Any, Iterable, Match, Optional, Pattern as _Pattern, overload
+from typing import Any, Iterable, Match, Pattern as _Pattern, overload
 
 SPECIAL_CHARS: str
 REPEAT_CHARS: str
@@ -37,7 +37,7 @@ if sys.version_info >= (3, 8):
 else:
     Pattern = _State
 
-_OpSubpatternType = tuple[Optional[int], int, int, SubPattern]
+_OpSubpatternType = tuple[int | None, int, int, SubPattern]
 _OpGroupRefExistsType = tuple[int, SubPattern, SubPattern]
 _OpInType = list[tuple[_NIC, int]]
 _OpBranchType = tuple[None, list[SubPattern]]
@@ -87,8 +87,8 @@ class Tokenizer:
 
 def fix_flags(src: str | bytes, flags: int) -> int: ...
 
-_TemplateType = tuple[list[tuple[int, int]], list[Optional[str]]]
-_TemplateByteType = tuple[list[tuple[int, int]], list[Optional[bytes]]]
+_TemplateType = tuple[list[tuple[int, int]], list[str | None]]
+_TemplateByteType = tuple[list[tuple[int, int]], list[bytes | None]]
 if sys.version_info >= (3, 8):
     def parse(str: str, flags: int = ..., state: State | None = ...) -> SubPattern: ...
     @overload

stdlib/ssl.pyi

@@ -9,7 +9,7 @@ _PCTRTT = tuple[tuple[str, str], ...]
 _PCTRTTT = tuple[_PCTRTT, ...]
 _PeerCertRetDictType = dict[str, str | _PCTRTTT | _PCTRTT]
 _PeerCertRetType = _PeerCertRetDictType | bytes | None
-_EnumRetType = list[tuple[bytes, str, Union[set[str], bool]]]
+_EnumRetType = list[tuple[bytes, str, set[str] | bool]]
 _PasswordType = Union[Callable[[], str | bytes], str, bytes]
 
 _SrvnmeCbType = Callable[[SSLSocket | SSLObject, str | None, SSLSocket], int | None]

stdlib/tkinter/font.pyi

@@ -1,7 +1,7 @@
 import _tkinter
 import sys
 import tkinter
-from typing import Any, Union, overload
+from typing import Any, overload
 from typing_extensions import Literal, TypedDict
 
 if sys.version_info >= (3, 9):
@@ -12,17 +12,13 @@ ROMAN: Literal["roman"]
 BOLD: Literal["bold"]
 ITALIC: Literal["italic"]
 
-_FontDescription = Union[
-    # "Helvetica 12"
-    str,
-    # A font object constructed in Python
-    Font,
-    # ("Helvetica", 12, BOLD)
-    list[Any],
-    tuple[Any, ...],
-    # A font object constructed in Tcl
-    _tkinter.Tcl_Obj,
-]
+_FontDescription = (
+    str  # "Helvetica 12"
+    | Font  # A font object constructed in Python
+    | list[Any]  # ("Helvetica", 12, BOLD)
+    | tuple[Any, ...]
+    | _tkinter.Tcl_Obj  # A font object constructed in Tcl
+)
 
 class _FontDict(TypedDict):
     family: str

stdlib/trace.pyi

@@ -1,7 +1,7 @@
 import sys
 import types
 from _typeshed import StrPath
-from typing import Any, Callable, Mapping, Optional, Sequence, TypeVar
+from typing import Any, Callable, Mapping, Sequence, TypeVar
 from typing_extensions import ParamSpec
 
 __all__ = ["Trace", "CoverageResults"]
@@ -9,7 +9,7 @@ __all__ = ["Trace", "CoverageResults"]
 _T = TypeVar("_T")
 _P = ParamSpec("_P")
 _localtrace = Callable[[types.FrameType, str, Any], Callable[..., Any]]
-_fileModuleFunction = tuple[str, Optional[str], str]
+_fileModuleFunction = tuple[str, str | None, str]
 
 class CoverageResults:
     def __init__(

stdlib/tracemalloc.pyi

@@ -1,6 +1,6 @@
 import sys
 from _tracemalloc import *
-from typing import Any, Optional, Sequence, Union, overload
+from typing import Any, Sequence, Union, overload
 from typing_extensions import SupportsIndex
 
 def get_object_traceback(obj: object) -> Traceback | None: ...
@@ -61,7 +61,7 @@ class Frame:
         def __le__(self, other: Frame, NotImplemented: Any = ...) -> bool: ...
 
 if sys.version_info >= (3, 9):
-    _TraceTupleT = Union[tuple[int, int, Sequence[_FrameTupleT], Optional[int]], tuple[int, int, Sequence[_FrameTupleT]]]
+    _TraceTupleT = Union[tuple[int, int, Sequence[_FrameTupleT], int | None], tuple[int, int, Sequence[_FrameTupleT]]]
 else:
     _TraceTupleT = tuple[int, int, Sequence[_FrameTupleT]]
 

stdlib/xmlrpc/server.pyi

@@ -3,11 +3,11 @@ import pydoc
 import socketserver
 import sys
 from datetime import datetime
-from typing import Any, Callable, Iterable, Mapping, Pattern, Protocol, Union
+from typing import Any, Callable, Iterable, Mapping, Pattern, Protocol
 from xmlrpc.client import Fault
 
 # TODO: Recursive type on tuple, list, dict
-_Marshallable = Union[None, bool, int, float, str, bytes, tuple[Any, ...], list[Any], dict[Any, Any], datetime]
+_Marshallable = None | bool | int | float | str | bytes | tuple[Any, ...] | list[Any] | dict[Any, Any] | datetime
 
 # The dispatch accepts anywhere from 0 to N arguments, no easy way to allow this in mypy
 class _DispatchArity0(Protocol):

stubs/Pillow/PIL/Image.pyi

@@ -22,7 +22,7 @@ _Box = tuple[int, int, int, int]
 _ConversionMatrix = Union[
     tuple[float, float, float, float], tuple[float, float, float, float, float, float, float, float, float, float, float, float],
 ]
-_Color = Union[float, tuple[float, ...]]
+_Color = float | tuple[float, ...]
 
 class _Writeable(SupportsWrite[bytes], Protocol):
     def seek(self, __offset: int) -> Any: ...