diff --git a/discord/ext/commands/converter.py b/discord/ext/commands/converter.py
index 3d706bf80..123b6699c 100644
--- a/discord/ext/commands/converter.py
+++ b/discord/ext/commands/converter.py
@@ -26,6 +26,7 @@ DEALINGS IN THE SOFTWARE.
 
 import re
 import inspect
+import typing
 
 import discord
 
@@ -555,6 +556,9 @@ class _Greedy:
         if converter is str or converter is type(None) or converter is _Greedy:
             raise TypeError('Greedy[%s] is invalid.' % converter.__name__)
 
+        if getattr(converter, '__origin__', None) is typing.Union and type(None) in converter.__args__:
+            raise TypeError('Greedy[%r] is invalid.' % converter)
+
         return self.__class__(converter=converter)
 
 Greedy = _Greedy()
diff --git a/docs/ext/commands/commands.rst b/docs/ext/commands/commands.rst
index fbf87fc27..523de3e3e 100644
--- a/docs/ext/commands/commands.rst
+++ b/docs/ext/commands/commands.rst
@@ -552,8 +552,8 @@ This command can be invoked any of the following ways:
     unintended parsing ambiguities in your code. One technique would be to clamp down the expected syntaxes
     allowed through custom converters or reordering the parameters to minimise clashes.
 
-    To help aid with some parsing ambiguities, :class:`str`, ``None`` and :data:`~ext.commands.Greedy` are
-    forbidden as parameters for the :data:`~ext.commands.Greedy` converter.
+    To help aid with some parsing ambiguities, :class:`str`, ``None``, :data:`typing.Optional` and
+    :data:`~ext.commands.Greedy` are forbidden as parameters for the :data:`~ext.commands.Greedy` converter.
 
 .. _ext_commands_error_handler: