diff --git a/python/ycm/client/base_request.py b/python/ycm/client/base_request.py
index 4c46a5d9..d67836a5 100644
--- a/python/ycm/client/base_request.py
+++ b/python/ycm/client/base_request.py
@@ -20,10 +20,15 @@
 import vim
 import json
 import requests
+from retries import retries
 from requests_futures.sessions import FuturesSession
+from concurrent.futures import ThreadPoolExecutor
 from ycm import vimsupport
 
 HEADERS = {'content-type': 'application/json'}
+# TODO: This TPE might be the reason we're shutting down slowly. It seems that
+# it waits for all worker threads to stop before letting the interpreter exit.
+EXECUTOR = ThreadPoolExecutor( max_workers = 4 )
 
 class ServerError( Exception ):
   def __init__( self, message ):
@@ -57,12 +62,24 @@ class BaseRequest( object ):
   # This returns a future! Use JsonFromFuture to get the value.
   @staticmethod
   def PostDataToHandlerAsync( data, handler ):
-    return BaseRequest.session.post( _BuildUri( handler ),
-                                     data = json.dumps( data ),
-                                     headers = HEADERS )
+    def PostData( data, handler ):
+      return BaseRequest.session.post( _BuildUri( handler ),
+                                      data = json.dumps( data ),
+                                      headers = HEADERS )
+
+    @retries( 3, delay = 0.5 )
+    def DelayedPostData( data, handler ):
+      return requests.post( _BuildUri( handler ),
+                            data = json.dumps( data ),
+                            headers = HEADERS )
+
+    if not _CheckServerIsHealthyWithCache():
+      return EXECUTOR.submit( DelayedPostData, data, handler )
+
+    return PostData( data, handler )
 
 
-  session = FuturesSession( max_workers = 4 )
+  session = FuturesSession( executor = EXECUTOR )
   server_location = 'http://localhost:6666'
 
 
@@ -102,3 +119,22 @@ def _BuildUri( handler ):
   return ''.join( [ BaseRequest.server_location, '/', handler ] )
 
 
+SERVER_HEALTHY = False
+
+def _CheckServerIsHealthyWithCache():
+  global SERVER_HEALTHY
+
+  def _ServerIsHealthy():
+    response = requests.get( _BuildUri( 'healthy' ) )
+    response.raise_for_status()
+    return response.json()
+
+  if SERVER_HEALTHY:
+    return True
+
+  try:
+    SERVER_HEALTHY = _ServerIsHealthy()
+    return SERVER_HEALTHY
+  except:
+    return False
+
diff --git a/python/ycm/client/event_notification.py b/python/ycm/client/event_notification.py
index 62c0fa65..c39a4f43 100644
--- a/python/ycm/client/event_notification.py
+++ b/python/ycm/client/event_notification.py
@@ -17,8 +17,6 @@
 # You should have received a copy of the GNU General Public License
 # along with YouCompleteMe.  If not, see <http://www.gnu.org/licenses/>.
 
-import traceback
-from ycm import vimsupport
 from ycm.client.base_request import BaseRequest, BuildRequestData
 
 
@@ -35,15 +33,7 @@ class EventNotification( BaseRequest ):
       request_data.update( self._extra_data )
     request_data[ 'event_name' ] = self._event_name
 
-    # On occasion, Vim tries to send event notifications to the server before
-    # it's up. This causes intrusive exception messages to interrupt the user.
-    # While we do want to log these exceptions just in case, we post them
-    # quietly to the Vim message log because nothing bad will happen if the
-    # server misses some events and we don't want to annoy the user.
-    try:
-      self.PostDataToHandlerAsync( request_data, 'event_notification' )
-    except:
-      vimsupport.EchoText( traceback.format_exc() )
+    self.PostDataToHandlerAsync( request_data, 'event_notification' )
 
 
 def SendEventNotificationAsync( event_name, extra_data = None ):