diff --git a/discord/errors.py b/discord/errors.py
index fec1f45db..bd78131a4 100644
--- a/discord/errors.py
+++ b/discord/errors.py
@@ -122,6 +122,14 @@ class NotFound(HTTPException):
     """
     pass
 
+class DiscordServerError(HTTPException):
+    """Exception that's thrown for when a 500 range status code occurs.
+
+    Subclass of :exc:`HTTPException`.
+
+    .. versionadded:: 1.5
+    """
+    pass
 
 class InvalidData(ClientException):
     """Exception that's raised when the library encounters unknown
diff --git a/discord/http.py b/discord/http.py
index d91664c97..1ad11d9e6 100644
--- a/discord/http.py
+++ b/discord/http.py
@@ -33,7 +33,7 @@ import weakref
 
 import aiohttp
 
-from .errors import HTTPException, Forbidden, NotFound, LoginFailure, GatewayNotFound
+from .errors import HTTPException, Forbidden, NotFound, LoginFailure, DiscordServerError, GatewayNotFound
 from .gateway import DiscordClientWebSocketResponse
 from . import __version__, utils
 
@@ -252,6 +252,9 @@ class HTTPClient:
                     raise
 
             # We've run out of retries, raise.
+            if r.status >= 500:
+                raise DiscordServerError(r, data)
+
             raise HTTPException(r, data)
 
     async def get_from_cdn(self, url):
@@ -659,7 +662,7 @@ class HTTPClient:
 
     def get_template(self, code):
         return self.request(Route('GET', '/guilds/templates/{code}', code=code))
-    
+
     def create_from_template(self, code, name, region, icon):
         payload = {
             'name': name,
diff --git a/discord/webhook.py b/discord/webhook.py
index 7824c55ae..bd2802302 100644
--- a/discord/webhook.py
+++ b/discord/webhook.py
@@ -34,7 +34,7 @@ from urllib.parse import quote as _uriquote
 import aiohttp
 
 from . import utils
-from .errors import InvalidArgument, HTTPException, Forbidden, NotFound
+from .errors import InvalidArgument, HTTPException, Forbidden, NotFound, DiscordServerError
 from .enums import try_enum, WebhookType
 from .user import BaseUser, User
 from .asset import Asset
@@ -241,7 +241,10 @@ class AsyncWebhookAdapter(WebhookAdapter):
                     raise NotFound(r, response)
                 else:
                     raise HTTPException(r, response)
+
         # no more retries
+        if r.status >= 500:
+            raise DiscordServerError(r, response)
         raise HTTPException(r, response)
 
     async def handle_execution_response(self, response, *, wait):
@@ -342,7 +345,10 @@ class RequestsWebhookAdapter(WebhookAdapter):
                 raise NotFound(r, response)
             else:
                 raise HTTPException(r, response)
+
         # no more retries
+        if r.status >= 500:
+            raise DiscordServerError(r, response)
         raise HTTPException(r, response)
 
     def handle_execution_response(self, response, *, wait):
diff --git a/docs/api.rst b/docs/api.rst
index 759aece6a..c97197cd5 100644
--- a/docs/api.rst
+++ b/docs/api.rst
@@ -904,7 +904,7 @@ of :class:`enum.Enum`.
     is to be interpreted as a system message or a regular message.
 
     .. container:: operations
-    
+
       .. describe:: x == y
 
           Checks if two messages are equal.
@@ -2902,6 +2902,8 @@ The following exceptions are thrown by the library.
 
 .. autoexception:: NotFound
 
+.. autoexception:: DiscordServerError
+
 .. autoexception:: InvalidData
 
 .. autoexception:: InvalidArgument
@@ -2931,3 +2933,4 @@ Exception Hierarchy
             - :exc:`HTTPException`
                 - :exc:`Forbidden`
                 - :exc:`NotFound`
+                - :exc:`DiscordServerError`