diff --git a/discord/http.py b/discord/http.py
index 2d3bb8e1c..bddf56e30 100644
--- a/discord/http.py
+++ b/discord/http.py
@@ -194,7 +194,7 @@ class HTTPClient:
                         continue
 
                     # we've received a 500 or 502, unconditional retry
-                    if r.status in {500, 502} and tries <= 5:
+                    if r.status in {500, 502}:
                         yield from asyncio.sleep(1 + tries * 2, loop=self.loop)
                         continue
 
@@ -208,6 +208,8 @@ class HTTPClient:
                 finally:
                     # clean-up just in case
                     yield from r.release()
+            # We've run out of retries, raise.
+            raise HTTPException(r, data)
 
     def get_attachment(self, url):
         resp = yield from self._session.get(url)