diff --git a/discord/ext/commands/_types.py b/discord/ext/commands/_types.py
index 89077664b..5c57a330e 100644
--- a/discord/ext/commands/_types.py
+++ b/discord/ext/commands/_types.py
@@ -23,7 +23,7 @@ DEALINGS IN THE SOFTWARE.
 """
 
 
-from typing import Any, Callable, Coroutine, TYPE_CHECKING, TypeVar, Union, Tuple
+from typing import Any, Awaitable, Callable, Coroutine, TYPE_CHECKING, TypeVar, Union, Tuple
 
 
 T = TypeVar('T')
@@ -37,18 +37,16 @@ if TYPE_CHECKING:
     from .errors import CommandError
 
     P = ParamSpec('P')
-    MaybeCoroFunc = Union[
-        Callable[P, 'Coro[T]'],
-        Callable[P, T],
-    ]
+    MaybeAwaitableFunc = Callable[P, 'MaybeAwaitable[T]']
 else:
     P = TypeVar('P')
-    MaybeCoroFunc = Tuple[P, T]
+    MaybeAwaitableFunc = Tuple[P, T]
 
 _Bot = Union['Bot', 'AutoShardedBot']
 Coro = Coroutine[Any, Any, T]
-MaybeCoro = Union[T, Coro[T]]
 CoroFunc = Callable[..., Coro[Any]]
+MaybeCoro = Union[T, Coro[T]]
+MaybeAwaitable = Union[T, Awaitable[T]]
 
 Check = Union[Callable[["Cog", "ContextT"], MaybeCoro[bool]], Callable[["ContextT"], MaybeCoro[bool]]]
 Hook = Union[Callable[["Cog", "ContextT"], Coro[Any]], Callable[["ContextT"], Coro[Any]]]
diff --git a/discord/ext/commands/bot.py b/discord/ext/commands/bot.py
index dde7545bd..d52194645 100644
--- a/discord/ext/commands/bot.py
+++ b/discord/ext/commands/bot.py
@@ -74,11 +74,11 @@ if TYPE_CHECKING:
         Check,
         CoroFunc,
         ContextT,
-        MaybeCoroFunc,
+        MaybeAwaitableFunc,
     )
 
     _Prefix = Union[Iterable[str], str]
-    _PrefixCallable = MaybeCoroFunc[[BotT, Message], _Prefix]
+    _PrefixCallable = MaybeAwaitableFunc[[BotT, Message], _Prefix]
     PrefixType = Union[_Prefix, _PrefixCallable[BotT]]
 
 __all__ = (
diff --git a/discord/ext/commands/help.py b/discord/ext/commands/help.py
index b0c3f7dc6..bf0e12104 100644
--- a/discord/ext/commands/help.py
+++ b/discord/ext/commands/help.py
@@ -31,6 +31,7 @@ import re
 
 from typing import (
     TYPE_CHECKING,
+    Awaitable,
     Optional,
     Generator,
     Generic,
@@ -54,7 +55,6 @@ if TYPE_CHECKING:
 
     import discord.abc
 
-    from ._types import Coro
     from .bot import BotBase
     from .cog import Cog
     from .context import Context
@@ -295,7 +295,7 @@ class HelpCommand(HelpCommandCommand, Generic[ContextT]):
         bot.remove_command(self.name)
         self._eject_cog()
 
-    async def _call_without_cog(self, callback: Callable[[ContextT], Coro[T]], ctx: ContextT) -> T:
+    async def _call_without_cog(self, callback: Callable[[ContextT], Awaitable[T]], ctx: ContextT) -> T:
         cog = self._cog
         self.cog = None
         try:
diff --git a/discord/member.py b/discord/member.py
index a8d1ca486..0b5ad4cbc 100644
--- a/discord/member.py
+++ b/discord/member.py
@@ -28,7 +28,7 @@ import datetime
 import inspect
 import itertools
 from operator import attrgetter
-from typing import Any, Callable, Collection, Coroutine, Dict, List, Optional, TYPE_CHECKING, Tuple, Union, Type
+from typing import Any, Awaitable, Callable, Collection, Dict, List, Optional, TYPE_CHECKING, Tuple, Union, Type
 
 import discord.abc
 
@@ -331,7 +331,7 @@ class Member(discord.abc.Messageable, _UserTag):
         default_avatar: Asset
         avatar: Optional[Asset]
         dm_channel: Optional[DMChannel]
-        create_dm: Callable[[], Coroutine[Any, Any, DMChannel]]
+        create_dm: Callable[[], Awaitable[DMChannel]]
         mutual_guilds: List[Guild]
         public_flags: PublicUserFlags
         banner: Optional[Asset]
diff --git a/discord/utils.py b/discord/utils.py
index aaa18b780..a3997930c 100644
--- a/discord/utils.py
+++ b/discord/utils.py
@@ -140,10 +140,7 @@ if TYPE_CHECKING:
 
     P = ParamSpec('P')
 
-    MaybeCoroFunc = Union[
-        Callable[P, Coroutine[Any, Any, 'T']],
-        Callable[P, 'T'],
-    ]
+    MaybeAwaitableFunc = Callable[P, 'MaybeAwaitable[T]']
 
     _SnowflakeListBase = array.array[int]
 
@@ -156,6 +153,7 @@ T = TypeVar('T')
 T_co = TypeVar('T_co', covariant=True)
 _Iter = Union[Iterable[T], AsyncIterable[T]]
 Coro = Coroutine[Any, Any, T]
+MaybeAwaitable = Union[T, Awaitable[T]]
 
 
 class CachedSlotProperty(Generic[T, T_co]):
@@ -615,7 +613,7 @@ def _parse_ratelimit_header(request: Any, *, use_clock: bool = False) -> float:
         return float(reset_after)
 
 
-async def maybe_coroutine(f: MaybeCoroFunc[P, T], *args: P.args, **kwargs: P.kwargs) -> T:
+async def maybe_coroutine(f: MaybeAwaitableFunc[P, T], *args: P.args, **kwargs: P.kwargs) -> T:
     value = f(*args, **kwargs)
     if _isawaitable(value):
         return await value