diff --git a/discord/abc.py b/discord/abc.py
index 726fe5567..dfc96761a 100644
--- a/discord/abc.py
+++ b/discord/abc.py
@@ -1391,15 +1391,10 @@ class Messageable:
         await self._state.http.send_typing(channel.id)
 
     def typing(self) -> Typing:
-        """Returns a context manager that allows you to type for an indefinite period of time.
+        """Returns an asynchronous context manager that allows you to type for an indefinite period of time.
 
         This is useful for denoting long computations in your bot.
 
-        .. note::
-
-            This is both a regular context manager and an async context manager.
-            This means that both ``with`` and ``async with`` work with this.
-
         Example Usage: ::
 
             async with channel.typing():
@@ -1408,6 +1403,8 @@ class Messageable:
 
             await channel.send('done!')
 
+        .. versionchanged:: 2.0
+            This no longer works with the ``with`` syntax, ``async with`` must be used instead.
         """
         return Typing(self)
 
diff --git a/discord/context_managers.py b/discord/context_managers.py
index 5ba6efbc1..e6aa67901 100644
--- a/discord/context_managers.py
+++ b/discord/context_managers.py
@@ -25,15 +25,13 @@ DEALINGS IN THE SOFTWARE.
 from __future__ import annotations
 
 import asyncio
-from typing import TYPE_CHECKING, TypeVar, Optional, Type
+from typing import TYPE_CHECKING, Optional, Type
 
 if TYPE_CHECKING:
     from .abc import Messageable
 
     from types import TracebackType
 
-    TypingT = TypeVar('TypingT', bound='Typing')
-
 # fmt: off
 __all__ = (
     'Typing',
@@ -66,23 +64,11 @@ class Typing:
             await typing(channel.id)
             await asyncio.sleep(5)
 
-    def __enter__(self: TypingT) -> TypingT:
-        self.task: asyncio.Task = self.loop.create_task(self.do_typing())
-        self.task.add_done_callback(_typing_done_callback)
-        return self
-
-    def __exit__(
-        self,
-        exc_type: Optional[Type[BaseException]],
-        exc_value: Optional[BaseException],
-        traceback: Optional[TracebackType],
-    ) -> None:
-        self.task.cancel()
-
-    async def __aenter__(self: TypingT) -> TypingT:
+    async def __aenter__(self) -> None:
         self._channel = channel = await self.messageable._get_channel()
         await channel._state.http.send_typing(channel.id)
-        return self.__enter__()
+        self.task: asyncio.Task = self.loop.create_task(self.do_typing())
+        self.task.add_done_callback(_typing_done_callback)
 
     async def __aexit__(
         self,