diff --git a/stubs/Jinja2/jinja2/nodes.pyi b/stubs/Jinja2/jinja2/nodes.pyi
index 84871975d..2f680dbc7 100644
--- a/stubs/Jinja2/jinja2/nodes.pyi
+++ b/stubs/Jinja2/jinja2/nodes.pyi
@@ -1,5 +1,5 @@
 import typing
-from typing import Any, Optional
+from typing import Any
 
 class Impossible(Exception): ...
 
@@ -10,7 +10,7 @@ class EvalContext:
     environment: Any
     autoescape: Any
     volatile: bool
-    def __init__(self, environment, template_name: Optional[Any] = ...) -> None: ...
+    def __init__(self, environment, template_name: Any | None = ...) -> None: ...
     def save(self): ...
     def revert(self, old): ...
 
@@ -21,8 +21,8 @@ class Node:
     attributes: Any
     abstract: bool
     def __init__(self, *fields, **attributes) -> None: ...
-    def iter_fields(self, exclude: Optional[Any] = ..., only: Optional[Any] = ...): ...
-    def iter_child_nodes(self, exclude: Optional[Any] = ..., only: Optional[Any] = ...): ...
+    def iter_fields(self, exclude: Any | None = ..., only: Any | None = ...): ...
+    def iter_child_nodes(self, exclude: Any | None = ..., only: Any | None = ...): ...
     def find(self, node_type): ...
     def find_all(self, node_type): ...
     def set_ctx(self, ctx): ...
@@ -89,20 +89,20 @@ class AssignBlock(Stmt):
 
 class Expr(Node):
     abstract: bool
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
     def can_assign(self): ...
 
 class BinExpr(Expr):
     fields: Any
     operator: Any
     abstract: bool
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class UnaryExpr(Expr):
     fields: Any
     operator: Any
     abstract: bool
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Name(Expr):
     fields: Any
@@ -113,71 +113,71 @@ class Literal(Expr):
 
 class Const(Literal):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
     @classmethod
-    def from_untrusted(cls, value, lineno: Optional[Any] = ..., environment: Optional[Any] = ...): ...
+    def from_untrusted(cls, value, lineno: Any | None = ..., environment: Any | None = ...): ...
 
 class TemplateData(Literal):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Tuple(Literal):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
     def can_assign(self): ...
 
 class List(Literal):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Dict(Literal):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Pair(Helper):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Keyword(Helper):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class CondExpr(Expr):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Filter(Expr):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Test(Expr):
     fields: Any
 
 class Call(Expr):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Getitem(Expr):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
     def can_assign(self): ...
 
 class Getattr(Expr):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
     def can_assign(self): ...
 
 class Slice(Expr):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Concat(Expr):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Compare(Expr):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Operand(Helper):
     fields: Any
@@ -205,11 +205,11 @@ class Pow(BinExpr):
 
 class And(BinExpr):
     operator: str
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Or(BinExpr):
     operator: str
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class Not(UnaryExpr):
     operator: str
@@ -235,11 +235,11 @@ class InternalName(Expr):
 
 class MarkSafe(Expr):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class MarkSafeIfAutoescape(Expr):
     fields: Any
-    def as_const(self, eval_ctx: Optional[Any] = ...): ...
+    def as_const(self, eval_ctx: Any | None = ...): ...
 
 class ContextReference(Expr): ...
 class Continue(Stmt): ...
diff --git a/stubs/click/click/core.pyi b/stubs/click/click/core.pyi
index e655f515a..bd7341852 100644
--- a/stubs/click/click/core.pyi
+++ b/stubs/click/click/core.pyi
@@ -21,53 +21,53 @@ from click.parser import OptionParser
 _CC = TypeVar("_CC", bound=Callable[[], Any])
 
 def invoke_param_callback(
-    callback: Callable[[Context, Parameter, Optional[str]], Any], ctx: Context, param: Parameter, value: Optional[str]
+    callback: Callable[[Context, Parameter, str | None], Any], ctx: Context, param: Parameter, value: str | None
 ) -> Any: ...
-def augment_usage_errors(ctx: Context, param: Optional[Parameter] = ...) -> ContextManager[None]: ...
+def augment_usage_errors(ctx: Context, param: Parameter | None = ...) -> ContextManager[None]: ...
 def iter_params_for_processing(
     invocation_order: Sequence[Parameter], declaration_order: Iterable[Parameter]
 ) -> Iterable[Parameter]: ...
 
 class Context:
-    parent: Optional[Context]
+    parent: Context | None
     command: Command
-    info_name: Optional[str]
+    info_name: str | None
     params: Dict[Any, Any]
     args: List[str]
     protected_args: List[str]
     obj: Any
-    default_map: Optional[Mapping[str, Any]]
-    invoked_subcommand: Optional[str]
-    terminal_width: Optional[int]
-    max_content_width: Optional[int]
+    default_map: Mapping[str, Any] | None
+    invoked_subcommand: str | None
+    terminal_width: int | None
+    max_content_width: int | None
     allow_extra_args: bool
     allow_interspersed_args: bool
     ignore_unknown_options: bool
     help_option_names: List[str]
-    token_normalize_func: Optional[Callable[[str], str]]
+    token_normalize_func: Callable[[str], str] | None
     resilient_parsing: bool
-    auto_envvar_prefix: Optional[str]
-    color: Optional[bool]
+    auto_envvar_prefix: str | None
+    color: bool | None
     _meta: Dict[str, Any]
     _close_callbacks: List[Any]
     _depth: int
     def __init__(
         self,
         command: Command,
-        parent: Optional[Context] = ...,
-        info_name: Optional[str] = ...,
-        obj: Optional[Any] = ...,
-        auto_envvar_prefix: Optional[str] = ...,
-        default_map: Optional[Mapping[str, Any]] = ...,
-        terminal_width: Optional[int] = ...,
-        max_content_width: Optional[int] = ...,
+        parent: Context | None = ...,
+        info_name: str | None = ...,
+        obj: Any | None = ...,
+        auto_envvar_prefix: str | None = ...,
+        default_map: Mapping[str, Any] | None = ...,
+        terminal_width: int | None = ...,
+        max_content_width: int | None = ...,
         resilient_parsing: bool = ...,
-        allow_extra_args: Optional[bool] = ...,
-        allow_interspersed_args: Optional[bool] = ...,
-        ignore_unknown_options: Optional[bool] = ...,
-        help_option_names: Optional[List[str]] = ...,
-        token_normalize_func: Optional[Callable[[str], str]] = ...,
-        color: Optional[bool] = ...,
+        allow_extra_args: bool | None = ...,
+        allow_interspersed_args: bool | None = ...,
+        ignore_unknown_options: bool | None = ...,
+        help_option_names: List[str] | None = ...,
+        token_normalize_func: Callable[[str], str] | None = ...,
+        color: bool | None = ...,
     ) -> None: ...
     @property
     def meta(self) -> Dict[str, Any]: ...
@@ -83,11 +83,11 @@ class Context:
     def lookup_default(self, name: str) -> Any: ...
     def fail(self, message: str) -> NoReturn: ...
     def abort(self) -> NoReturn: ...
-    def exit(self, code: Union[int, str] = ...) -> NoReturn: ...
+    def exit(self, code: int | str = ...) -> NoReturn: ...
     def get_usage(self) -> str: ...
     def get_help(self) -> str: ...
-    def invoke(self, callback: Union[Command, Callable[..., Any]], *args: Any, **kwargs: Any) -> Any: ...
-    def forward(self, callback: Union[Command, Callable[..., Any]], *args: Any, **kwargs: Any) -> Any: ...
+    def invoke(self, callback: Command | Callable[..., Any], *args: Any, **kwargs: Any) -> Any: ...
+    def forward(self, callback: Command | Callable[..., Any], *args: Any, **kwargs: Any) -> Any: ...
 
 class BaseCommand:
     allow_extra_args: bool
@@ -95,28 +95,28 @@ class BaseCommand:
     ignore_unknown_options: bool
     name: str
     context_settings: Dict[Any, Any]
-    def __init__(self, name: str, context_settings: Optional[Dict[Any, Any]] = ...) -> None: ...
+    def __init__(self, name: str, context_settings: Dict[Any, Any] | None = ...) -> None: ...
     def get_usage(self, ctx: Context) -> str: ...
     def get_help(self, ctx: Context) -> str: ...
-    def make_context(self, info_name: str, args: List[str], parent: Optional[Context] = ..., **extra: Any) -> Context: ...
+    def make_context(self, info_name: str, args: List[str], parent: Context | None = ..., **extra: Any) -> Context: ...
     def parse_args(self, ctx: Context, args: List[str]) -> List[str]: ...
     def invoke(self, ctx: Context) -> Any: ...
     def main(
         self,
-        args: Optional[List[str]] = ...,
-        prog_name: Optional[str] = ...,
-        complete_var: Optional[str] = ...,
+        args: List[str] | None = ...,
+        prog_name: str | None = ...,
+        complete_var: str | None = ...,
         standalone_mode: bool = ...,
         **extra: Any,
     ) -> Any: ...
     def __call__(self, *args: Any, **kwargs: Any) -> Any: ...
 
 class Command(BaseCommand):
-    callback: Optional[Callable[..., Any]]
+    callback: Callable[..., Any] | None
     params: List[Parameter]
-    help: Optional[str]
-    epilog: Optional[str]
-    short_help: Optional[str]
+    help: str | None
+    epilog: str | None
+    short_help: str | None
     options_metavar: str
     add_help_option: bool
     no_args_is_help: bool
@@ -125,12 +125,12 @@ class Command(BaseCommand):
     def __init__(
         self,
         name: str,
-        context_settings: Optional[Dict[Any, Any]] = ...,
-        callback: Optional[Callable[..., Any]] = ...,
-        params: Optional[List[Parameter]] = ...,
-        help: Optional[str] = ...,
-        epilog: Optional[str] = ...,
-        short_help: Optional[str] = ...,
+        context_settings: Dict[Any, Any] | None = ...,
+        callback: Callable[..., Any] | None = ...,
+        params: List[Parameter] | None = ...,
+        help: str | None = ...,
+        epilog: str | None = ...,
+        short_help: str | None = ...,
         options_metavar: str = ...,
         add_help_option: bool = ...,
         no_args_is_help: bool = ...,
@@ -141,7 +141,7 @@ class Command(BaseCommand):
     def format_usage(self, ctx: Context, formatter: HelpFormatter) -> None: ...
     def collect_usage_pieces(self, ctx: Context) -> List[str]: ...
     def get_help_option_names(self, ctx: Context) -> Set[str]: ...
-    def get_help_option(self, ctx: Context) -> Optional[Option]: ...
+    def get_help_option(self, ctx: Context) -> Option | None: ...
     def make_parser(self, ctx: Context) -> OptionParser: ...
     def get_short_help_str(self, limit: int = ...) -> str: ...
     def format_help(self, ctx: Context, formatter: HelpFormatter) -> None: ...
@@ -160,42 +160,42 @@ class MultiCommand(Command):
     result_callback: Callable[..., Any]
     def __init__(
         self,
-        name: Optional[str] = ...,
+        name: str | None = ...,
         invoke_without_command: bool = ...,
-        no_args_is_help: Optional[bool] = ...,
-        subcommand_metavar: Optional[str] = ...,
+        no_args_is_help: bool | None = ...,
+        subcommand_metavar: str | None = ...,
         chain: bool = ...,
-        result_callback: Optional[Callable[..., Any]] = ...,
+        result_callback: Callable[..., Any] | None = ...,
         **attrs: Any,
     ) -> None: ...
     def resultcallback(self, replace: bool = ...) -> Callable[[_F], _F]: ...
     def format_commands(self, ctx: Context, formatter: HelpFormatter) -> None: ...
     def resolve_command(self, ctx: Context, args: List[str]) -> Tuple[str, Command, List[str]]: ...
-    def get_command(self, ctx: Context, cmd_name: str) -> Optional[Command]: ...
+    def get_command(self, ctx: Context, cmd_name: str) -> Command | None: ...
     def list_commands(self, ctx: Context) -> Iterable[str]: ...
 
 class Group(MultiCommand):
     commands: Dict[str, Command]
-    def __init__(self, name: Optional[str] = ..., commands: Optional[Dict[str, Command]] = ..., **attrs: Any) -> None: ...
-    def add_command(self, cmd: Command, name: Optional[str] = ...) -> None: ...
+    def __init__(self, name: str | None = ..., commands: Dict[str, Command] | None = ..., **attrs: Any) -> None: ...
+    def add_command(self, cmd: Command, name: str | None = ...) -> None: ...
     def command(self, *args: Any, **kwargs: Any) -> Callable[[Callable[..., Any]], Command]: ...
     def group(self, *args: Any, **kwargs: Any) -> Callable[[Callable[..., Any]], Group]: ...
 
 class CommandCollection(MultiCommand):
     sources: List[MultiCommand]
-    def __init__(self, name: Optional[str] = ..., sources: Optional[List[MultiCommand]] = ..., **attrs: Any) -> None: ...
+    def __init__(self, name: str | None = ..., sources: List[MultiCommand] | None = ..., **attrs: Any) -> None: ...
     def add_source(self, multi_cmd: MultiCommand) -> None: ...
 
 class _ParamType:
     name: str
     is_composite: bool
-    envvar_list_splitter: Optional[str]
-    def __call__(self, value: Optional[str], param: Optional[Parameter] = ..., ctx: Optional[Context] = ...) -> Any: ...
+    envvar_list_splitter: str | None
+    def __call__(self, value: str | None, param: Parameter | None = ..., ctx: Context | None = ...) -> Any: ...
     def get_metavar(self, param: Parameter) -> str: ...
     def get_missing_message(self, param: Parameter) -> str: ...
-    def convert(self, value: str, param: Optional[Parameter], ctx: Optional[Context]) -> Any: ...
+    def convert(self, value: str, param: Parameter | None, ctx: Context | None) -> Any: ...
     def split_envvar_value(self, rv: str) -> List[str]: ...
-    def fail(self, message: str, param: Optional[Parameter] = ..., ctx: Optional[Context] = ...) -> NoReturn: ...
+    def fail(self, message: str, param: Parameter | None = ..., ctx: Context | None = ...) -> NoReturn: ...
 
 # This type is here to resolve https://github.com/python/mypy/issues/5275
 _ConvertibleType = Union[
@@ -209,26 +209,26 @@ class Parameter:
     secondary_opts: List[str]
     type: _ParamType
     required: bool
-    callback: Optional[Callable[[Context, Parameter, str], Any]]
+    callback: Callable[[Context, Parameter, str], Any] | None
     nargs: int
     multiple: bool
     expose_value: bool
     default: Any
     is_eager: bool
-    metavar: Optional[str]
-    envvar: Union[str, List[str], None]
+    metavar: str | None
+    envvar: str | List[str] | None
     def __init__(
         self,
-        param_decls: Optional[Iterable[str]] = ...,
-        type: Optional[_ConvertibleType] = ...,
+        param_decls: Iterable[str] | None = ...,
+        type: _ConvertibleType | None = ...,
         required: bool = ...,
-        default: Optional[Any] = ...,
-        callback: Optional[Callable[[Context, Parameter, str], Any]] = ...,
-        nargs: Optional[int] = ...,
-        metavar: Optional[str] = ...,
+        default: Any | None = ...,
+        callback: Callable[[Context, Parameter, str], Any] | None = ...,
+        nargs: int | None = ...,
+        metavar: str | None = ...,
         expose_value: bool = ...,
         is_eager: bool = ...,
-        envvar: Optional[Union[str, List[str]]] = ...,
+        envvar: str | List[str] | None = ...,
     ) -> None: ...
     @property
     def human_readable_name(self) -> str: ...
@@ -241,7 +241,7 @@ class Parameter:
     def value_is_missing(self, value: Any) -> bool: ...
     def full_process_value(self, ctx: Context, value: Any) -> Any: ...
     def resolve_envvar_value(self, ctx: Context) -> str: ...
-    def value_from_envvar(self, ctx: Context) -> Union[str, List[str]]: ...
+    def value_from_envvar(self, ctx: Context) -> str | List[str]: ...
     def handle_parse_result(self, ctx: Context, opts: Dict[str, Any], args: List[str]) -> Tuple[Any, List[str]]: ...
     def get_help_record(self, ctx: Context) -> Tuple[str, str]: ...
     def get_usage_pieces(self, ctx: Context) -> List[str]: ...
@@ -257,25 +257,25 @@ class Option(Parameter):
     count: bool
     multiple: bool
     allow_from_autoenv: bool
-    help: Optional[str]
+    help: str | None
     hidden: bool
     show_default: bool
     show_choices: bool
     show_envvar: bool
     def __init__(
         self,
-        param_decls: Optional[Iterable[str]] = ...,
+        param_decls: Iterable[str] | None = ...,
         show_default: bool = ...,
-        prompt: Union[bool, str] = ...,
+        prompt: bool | str = ...,
         confirmation_prompt: bool = ...,
         hide_input: bool = ...,
-        is_flag: Optional[bool] = ...,
-        flag_value: Optional[Any] = ...,
+        is_flag: bool | None = ...,
+        flag_value: Any | None = ...,
         multiple: bool = ...,
         count: bool = ...,
         allow_from_autoenv: bool = ...,
-        type: Optional[_ConvertibleType] = ...,
-        help: Optional[str] = ...,
+        type: _ConvertibleType | None = ...,
+        help: str | None = ...,
         hidden: bool = ...,
         show_choices: bool = ...,
         show_envvar: bool = ...,
@@ -284,4 +284,4 @@ class Option(Parameter):
     def prompt_for_value(self, ctx: Context) -> Any: ...
 
 class Argument(Parameter):
-    def __init__(self, param_decls: Optional[Iterable[str]] = ..., required: Optional[bool] = ..., **attrs: Any) -> None: ...
+    def __init__(self, param_decls: Iterable[str] | None = ..., required: bool | None = ..., **attrs: Any) -> None: ...
diff --git a/stubs/requests/requests/sessions.pyi b/stubs/requests/requests/sessions.pyi
index e3d3c3a34..dfddaee4f 100644
--- a/stubs/requests/requests/sessions.pyi
+++ b/stubs/requests/requests/sessions.pyi
@@ -62,13 +62,13 @@ _SessionT = TypeVar("_SessionT", bound=Session)
 class Session(SessionRedirectMixin):
     __attrs__: Any
     headers: CaseInsensitiveDict[Text]
-    auth: Union[None, Tuple[Text, Text], _auth.AuthBase, Callable[[PreparedRequest], PreparedRequest]]
+    auth: None | Tuple[Text, Text] | _auth.AuthBase | Callable[[PreparedRequest], PreparedRequest]
     proxies: MutableMapping[Text, Text]
     hooks: _Hooks
     params: _Params
     stream: bool
-    verify: Union[None, bool, Text]
-    cert: Union[None, Text, Tuple[Text, Text]]
+    verify: None | bool | Text
+    cert: None | Text | Tuple[Text, Text]
     max_redirects: int
     trust_env: bool
     cookies: RequestsCookieJar
@@ -81,152 +81,152 @@ class Session(SessionRedirectMixin):
     def request(
         self,
         method: str,
-        url: Union[str, bytes, Text],
-        params: Optional[_Params] = ...,
+        url: str | bytes | Text,
+        params: _Params | None = ...,
         data: _Data = ...,
-        headers: Optional[MutableMapping[Text, Text]] = ...,
-        cookies: Union[None, RequestsCookieJar, MutableMapping[Text, Text]] = ...,
-        files: Optional[MutableMapping[Text, IO[Any]]] = ...,
-        auth: Union[None, Tuple[Text, Text], _auth.AuthBase, Callable[[PreparedRequest], PreparedRequest]] = ...,
-        timeout: Union[None, float, Tuple[float, float], Tuple[float, None]] = ...,
-        allow_redirects: Optional[bool] = ...,
-        proxies: Optional[MutableMapping[Text, Text]] = ...,
-        hooks: Optional[_HooksInput] = ...,
-        stream: Optional[bool] = ...,
-        verify: Union[None, bool, Text] = ...,
-        cert: Union[Text, Tuple[Text, Text], None] = ...,
-        json: Optional[Any] = ...,
+        headers: MutableMapping[Text, Text] | None = ...,
+        cookies: None | RequestsCookieJar | MutableMapping[Text, Text] = ...,
+        files: MutableMapping[Text, IO[Any]] | None = ...,
+        auth: None | Tuple[Text, Text] | _auth.AuthBase | Callable[[PreparedRequest], PreparedRequest] = ...,
+        timeout: None | float | Tuple[float, float] | Tuple[float, None] = ...,
+        allow_redirects: bool | None = ...,
+        proxies: MutableMapping[Text, Text] | None = ...,
+        hooks: _HooksInput | None = ...,
+        stream: bool | None = ...,
+        verify: None | bool | Text = ...,
+        cert: Text | Tuple[Text, Text] | None = ...,
+        json: Any | None = ...,
     ) -> Response: ...
     def get(
         self,
-        url: Union[Text, bytes],
-        params: Optional[_Params] = ...,
-        data: Optional[Any] = ...,
-        headers: Optional[Any] = ...,
-        cookies: Optional[Any] = ...,
-        files: Optional[Any] = ...,
-        auth: Optional[Any] = ...,
-        timeout: Optional[Any] = ...,
+        url: Text | bytes,
+        params: _Params | None = ...,
+        data: Any | None = ...,
+        headers: Any | None = ...,
+        cookies: Any | None = ...,
+        files: Any | None = ...,
+        auth: Any | None = ...,
+        timeout: Any | None = ...,
         allow_redirects: bool = ...,
-        proxies: Optional[Any] = ...,
-        hooks: Optional[Any] = ...,
-        stream: Optional[Any] = ...,
-        verify: Optional[Any] = ...,
-        cert: Optional[Any] = ...,
-        json: Optional[Any] = ...,
+        proxies: Any | None = ...,
+        hooks: Any | None = ...,
+        stream: Any | None = ...,
+        verify: Any | None = ...,
+        cert: Any | None = ...,
+        json: Any | None = ...,
     ) -> Response: ...
     def options(
         self,
-        url: Union[Text, bytes],
-        params: Optional[_Params] = ...,
-        data: Optional[Any] = ...,
-        headers: Optional[Any] = ...,
-        cookies: Optional[Any] = ...,
-        files: Optional[Any] = ...,
-        auth: Optional[Any] = ...,
-        timeout: Optional[Any] = ...,
+        url: Text | bytes,
+        params: _Params | None = ...,
+        data: Any | None = ...,
+        headers: Any | None = ...,
+        cookies: Any | None = ...,
+        files: Any | None = ...,
+        auth: Any | None = ...,
+        timeout: Any | None = ...,
         allow_redirects: bool = ...,
-        proxies: Optional[Any] = ...,
-        hooks: Optional[Any] = ...,
-        stream: Optional[Any] = ...,
-        verify: Optional[Any] = ...,
-        cert: Optional[Any] = ...,
-        json: Optional[Any] = ...,
+        proxies: Any | None = ...,
+        hooks: Any | None = ...,
+        stream: Any | None = ...,
+        verify: Any | None = ...,
+        cert: Any | None = ...,
+        json: Any | None = ...,
     ) -> Response: ...
     def head(
         self,
-        url: Union[Text, bytes],
-        params: Optional[_Params] = ...,
-        data: Optional[Any] = ...,
-        headers: Optional[Any] = ...,
-        cookies: Optional[Any] = ...,
-        files: Optional[Any] = ...,
-        auth: Optional[Any] = ...,
-        timeout: Optional[Any] = ...,
+        url: Text | bytes,
+        params: _Params | None = ...,
+        data: Any | None = ...,
+        headers: Any | None = ...,
+        cookies: Any | None = ...,
+        files: Any | None = ...,
+        auth: Any | None = ...,
+        timeout: Any | None = ...,
         allow_redirects: bool = ...,
-        proxies: Optional[Any] = ...,
-        hooks: Optional[Any] = ...,
-        stream: Optional[Any] = ...,
-        verify: Optional[Any] = ...,
-        cert: Optional[Any] = ...,
-        json: Optional[Any] = ...,
+        proxies: Any | None = ...,
+        hooks: Any | None = ...,
+        stream: Any | None = ...,
+        verify: Any | None = ...,
+        cert: Any | None = ...,
+        json: Any | None = ...,
     ) -> Response: ...
     def post(
         self,
-        url: Union[Text, bytes],
+        url: Text | bytes,
         data: _Data = ...,
-        json: Optional[Any] = ...,
-        params: Optional[_Params] = ...,
-        headers: Optional[Any] = ...,
-        cookies: Optional[Any] = ...,
-        files: Optional[Any] = ...,
-        auth: Optional[Any] = ...,
-        timeout: Optional[Any] = ...,
+        json: Any | None = ...,
+        params: _Params | None = ...,
+        headers: Any | None = ...,
+        cookies: Any | None = ...,
+        files: Any | None = ...,
+        auth: Any | None = ...,
+        timeout: Any | None = ...,
         allow_redirects: bool = ...,
-        proxies: Optional[Any] = ...,
-        hooks: Optional[Any] = ...,
-        stream: Optional[Any] = ...,
-        verify: Optional[Any] = ...,
-        cert: Optional[Any] = ...,
+        proxies: Any | None = ...,
+        hooks: Any | None = ...,
+        stream: Any | None = ...,
+        verify: Any | None = ...,
+        cert: Any | None = ...,
     ) -> Response: ...
     def put(
         self,
-        url: Union[Text, bytes],
+        url: Text | bytes,
         data: _Data = ...,
-        params: Optional[_Params] = ...,
-        headers: Optional[Any] = ...,
-        cookies: Optional[Any] = ...,
-        files: Optional[Any] = ...,
-        auth: Optional[Any] = ...,
-        timeout: Optional[Any] = ...,
+        params: _Params | None = ...,
+        headers: Any | None = ...,
+        cookies: Any | None = ...,
+        files: Any | None = ...,
+        auth: Any | None = ...,
+        timeout: Any | None = ...,
         allow_redirects: bool = ...,
-        proxies: Optional[Any] = ...,
-        hooks: Optional[Any] = ...,
-        stream: Optional[Any] = ...,
-        verify: Optional[Any] = ...,
-        cert: Optional[Any] = ...,
-        json: Optional[Any] = ...,
+        proxies: Any | None = ...,
+        hooks: Any | None = ...,
+        stream: Any | None = ...,
+        verify: Any | None = ...,
+        cert: Any | None = ...,
+        json: Any | None = ...,
     ) -> Response: ...
     def patch(
         self,
-        url: Union[Text, bytes],
+        url: Text | bytes,
         data: _Data = ...,
-        params: Optional[_Params] = ...,
-        headers: Optional[Any] = ...,
-        cookies: Optional[Any] = ...,
-        files: Optional[Any] = ...,
-        auth: Optional[Any] = ...,
-        timeout: Optional[Any] = ...,
+        params: _Params | None = ...,
+        headers: Any | None = ...,
+        cookies: Any | None = ...,
+        files: Any | None = ...,
+        auth: Any | None = ...,
+        timeout: Any | None = ...,
         allow_redirects: bool = ...,
-        proxies: Optional[Any] = ...,
-        hooks: Optional[Any] = ...,
-        stream: Optional[Any] = ...,
-        verify: Optional[Any] = ...,
-        cert: Optional[Any] = ...,
-        json: Optional[Any] = ...,
+        proxies: Any | None = ...,
+        hooks: Any | None = ...,
+        stream: Any | None = ...,
+        verify: Any | None = ...,
+        cert: Any | None = ...,
+        json: Any | None = ...,
     ) -> Response: ...
     def delete(
         self,
-        url: Union[Text, bytes],
-        params: Optional[_Params] = ...,
-        data: Optional[Any] = ...,
-        headers: Optional[Any] = ...,
-        cookies: Optional[Any] = ...,
-        files: Optional[Any] = ...,
-        auth: Optional[Any] = ...,
-        timeout: Optional[Any] = ...,
+        url: Text | bytes,
+        params: _Params | None = ...,
+        data: Any | None = ...,
+        headers: Any | None = ...,
+        cookies: Any | None = ...,
+        files: Any | None = ...,
+        auth: Any | None = ...,
+        timeout: Any | None = ...,
         allow_redirects: bool = ...,
-        proxies: Optional[Any] = ...,
-        hooks: Optional[Any] = ...,
-        stream: Optional[Any] = ...,
-        verify: Optional[Any] = ...,
-        cert: Optional[Any] = ...,
-        json: Optional[Any] = ...,
+        proxies: Any | None = ...,
+        hooks: Any | None = ...,
+        stream: Any | None = ...,
+        verify: Any | None = ...,
+        cert: Any | None = ...,
+        json: Any | None = ...,
     ) -> Response: ...
     def send(self, request: PreparedRequest, **kwargs) -> Response: ...
     def merge_environment_settings(self, url, proxies, stream, verify, cert): ...
     def get_adapter(self, url): ...
     def close(self) -> None: ...
-    def mount(self, prefix: Union[Text, bytes], adapter: BaseAdapter) -> None: ...
+    def mount(self, prefix: Text | bytes, adapter: BaseAdapter) -> None: ...
 
 def session() -> Session: ...
diff --git a/stubs/six/six/__init__.pyi b/stubs/six/six/__init__.pyi
index 80b21672d..bf22203db 100644
--- a/stubs/six/six/__init__.pyi
+++ b/stubs/six/six/__init__.pyi
@@ -16,12 +16,10 @@ from typing import (
     KeysView,
     Mapping,
     NoReturn,
-    Optional,
     Pattern,
     Tuple,
     Type,
     TypeVar,
-    Union,
     ValuesView,
     overload,
 )
@@ -56,10 +54,10 @@ def create_unbound_method(func: types.FunctionType, cls: type) -> types.Function
 Iterator = object
 
 def get_method_function(meth: types.MethodType) -> types.FunctionType: ...
-def get_method_self(meth: types.MethodType) -> Optional[object]: ...
-def get_function_closure(fun: types.FunctionType) -> Optional[Tuple[types._Cell, ...]]: ...
+def get_method_self(meth: types.MethodType) -> object | None: ...
+def get_function_closure(fun: types.FunctionType) -> Tuple[types._Cell, ...] | None: ...
 def get_function_code(fun: types.FunctionType) -> types.CodeType: ...
-def get_function_defaults(fun: types.FunctionType) -> Optional[Tuple[Any, ...]]: ...
+def get_function_defaults(fun: types.FunctionType) -> Tuple[Any, ...] | None: ...
 def get_function_globals(fun: types.FunctionType) -> Dict[str, Any]: ...
 def iterkeys(d: Mapping[_K, Any]) -> typing.Iterator[_K]: ...
 def itervalues(d: Mapping[Any, _V]) -> typing.Iterator[_V]: ...
@@ -79,47 +77,43 @@ def int2byte(i: int) -> bytes: ...
 def byte2int(bs: binary_type) -> int: ...
 def indexbytes(buf: binary_type, i: int) -> int: ...
 def iterbytes(buf: binary_type) -> typing.Iterator[int]: ...
-def assertCountEqual(self: unittest.TestCase, first: Iterable[_T], second: Iterable[_T], msg: Optional[str] = ...) -> None: ...
+def assertCountEqual(self: unittest.TestCase, first: Iterable[_T], second: Iterable[_T], msg: str | None = ...) -> None: ...
 @overload
-def assertRaisesRegex(self: unittest.TestCase, msg: Optional[str] = ...) -> Any: ...
+def assertRaisesRegex(self: unittest.TestCase, msg: str | None = ...) -> Any: ...
 @overload
 def assertRaisesRegex(self: unittest.TestCase, callable_obj: Callable[..., Any], *args: Any, **kwargs: Any) -> Any: ...
 def assertRegex(
-    self: unittest.TestCase, text: AnyStr, expected_regex: Union[AnyStr, Pattern[AnyStr]], msg: Optional[str] = ...
+    self: unittest.TestCase, text: AnyStr, expected_regex: AnyStr | Pattern[AnyStr], msg: str | None = ...
 ) -> None: ...
 
 exec_ = exec
 
-def reraise(
-    tp: Optional[Type[BaseException]], value: Optional[BaseException], tb: Optional[types.TracebackType] = ...
-) -> NoReturn: ...
-def raise_from(value: Union[BaseException, Type[BaseException]], from_value: Optional[BaseException]) -> NoReturn: ...
+def reraise(tp: Type[BaseException] | None, value: BaseException | None, tb: types.TracebackType | None = ...) -> NoReturn: ...
+def raise_from(value: BaseException | Type[BaseException], from_value: BaseException | None) -> NoReturn: ...
 
 print_ = print
 
 def with_metaclass(meta: type, *bases: type) -> type: ...
 def add_metaclass(metaclass: type) -> Callable[[_T], _T]: ...
-def ensure_binary(s: Union[bytes, str], encoding: str = ..., errors: str = ...) -> bytes: ...
-def ensure_str(s: Union[bytes, str], encoding: str = ..., errors: str = ...) -> str: ...
-def ensure_text(s: Union[bytes, str], encoding: str = ..., errors: str = ...) -> str: ...
+def ensure_binary(s: bytes | str, encoding: str = ..., errors: str = ...) -> bytes: ...
+def ensure_str(s: bytes | str, encoding: str = ..., errors: str = ...) -> str: ...
+def ensure_text(s: bytes | str, encoding: str = ..., errors: str = ...) -> str: ...
 def python_2_unicode_compatible(klass: _T) -> _T: ...
 
 class _LazyDescriptor:
     name: str
     def __init__(self, name: str) -> None: ...
-    def __get__(self, obj: Optional[object], type: Optional[type] = ...) -> Any: ...
+    def __get__(self, obj: object | None, type: type | None = ...) -> Any: ...
 
 class MovedModule(_LazyDescriptor):
     mod: str
-    def __init__(self, name: str, old: str, new: Optional[str] = ...) -> None: ...
+    def __init__(self, name: str, old: str, new: str | None = ...) -> None: ...
     def __getattr__(self, attr: str) -> Any: ...
 
 class MovedAttribute(_LazyDescriptor):
     mod: str
     attr: str
-    def __init__(
-        self, name: str, old_mod: str, new_mod: str, old_attr: Optional[str] = ..., new_attr: Optional[str] = ...
-    ) -> None: ...
+    def __init__(self, name: str, old_mod: str, new_mod: str, old_attr: str | None = ..., new_attr: str | None = ...) -> None: ...
 
-def add_move(move: Union[MovedModule, MovedAttribute]) -> None: ...
+def add_move(move: MovedModule | MovedAttribute) -> None: ...
 def remove_move(name: str) -> None: ...