diff --git a/rhodecode/integrations/types/webhook.py b/rhodecode/integrations/types/webhook.py
--- a/rhodecode/integrations/types/webhook.py
+++ b/rhodecode/integrations/types/webhook.py
@@ -255,14 +255,13 @@ class WebhookIntegrationType(Integration
 @task(ignore_result=True)
 def post_to_webhook(url_calls, settings):
     max_retries = 3
+    retries = Retry(
+        total=max_retries,
+        backoff_factor=0.15,
+        status_forcelist=[500, 502, 503, 504])
     for url, token, data in url_calls:
-        # retry max N times
-        retries = Retry(
-            total=max_retries,
-            backoff_factor=0.15,
-            status_forcelist=[500, 502, 503, 504])
         req_session = requests.Session()
-        req_session.mount(
+        req_session.mount(  # retry max N times
             'http://', requests.adapters.HTTPAdapter(max_retries=retries))
 
         method = settings.get('method_type') or 'post'
diff --git a/rhodecode/lib/vcs/client_http.py b/rhodecode/lib/vcs/client_http.py
--- a/rhodecode/lib/vcs/client_http.py
+++ b/rhodecode/lib/vcs/client_http.py
@@ -32,6 +32,7 @@ import uuid
 import pycurl
 import msgpack
 import requests
+from requests.packages.urllib3.util.retry import Retry
 
 from . import exceptions, CurlSession
 
@@ -232,7 +233,11 @@ class VcsHttpProxy(object):
     CHUNK_SIZE = 16384
 
     def __init__(self, server_and_port, backend_endpoint):
-        adapter = requests.adapters.HTTPAdapter(max_retries=5)
+
+
+        retries = Retry(total=5, connect=None, read=None, redirect=None)
+
+        adapter = requests.adapters.HTTPAdapter(max_retries=retries)
         self.base_url = urlparse.urljoin(
             'http://%s' % server_and_port, backend_endpoint)
         self.session = requests.Session()