diff --git a/redbot/core/commands/context.py b/redbot/core/commands/context.py
index c956db112..71434a511 100644
--- a/redbot/core/commands/context.py
+++ b/redbot/core/commands/context.py
@@ -248,8 +248,11 @@ class Context(DPYContext):
             see `discord.abc.Messageable.send`
         discord.HTTPException
             see `discord.abc.Messageable.send`
+        ValueError
+            when the message's length is not between 1 and 2000 characters.
         """
-
+        if not message or len(message) > 2000:
+            raise ValueError("Message length must be between 1 and 2000")
         if await self.embed_requested():
             return await self.send(
                 embed=discord.Embed(description=message, color=(await self.embed_colour()))