diff --git a/cassandra/connection.py b/cassandra/connection.py
index 4ca458bf..6f60025b 100644
--- a/cassandra/connection.py
+++ b/cassandra/connection.py
@@ -121,7 +121,6 @@ class _Frame(object):
 
 NONBLOCKING = (errno.EAGAIN, errno.EWOULDBLOCK)
 
-
 class ConnectionException(Exception):
     """
     An unrecoverable error was hit when attempting to use a connection,
@@ -187,6 +186,8 @@ else:
 
 class Connection(object):
 
+    CALLBACK_ERR_THREAD_THRESHOLD = 100
+
     in_buffer_size = 4096
     out_buffer_size = 4096
 
@@ -354,8 +355,12 @@ class Connection(object):
         with self.lock:
             requests = self._requests
             self._requests = {}
+
+        if not requests:
+            return
+
         new_exc = ConnectionShutdown(str(exc))
-        for cb, _ in requests.values():
+        def try_callback(cb):
             try:
                 cb(new_exc)
             except Exception:
@@ -363,6 +368,28 @@ class Connection(object):
                             "failed connection (%s) to host %s:",
                             id(self), self.host, exc_info=True)
 
+        # run first callback from this thread to ensure pool state before leaving
+        cb, _ = requests.popitem()[1]
+        try_callback(cb)
+
+        if not requests:
+            return
+
+        # additional requests are optionally errored from a separate thread
+        # The default callback and retry logic is fairly expensive -- we don't
+        # want to tie up the event thread when there are many requests
+        def err_all_callbacks():
+            for cb, _ in requests.values():
+                try_callback(cb)
+        if len(requests) < Connection.CALLBACK_ERR_THREAD_THRESHOLD:
+            err_all_callbacks()
+        else:
+            # daemon thread here because we want to stay decoupled from the cluster TPE
+            # TODO: would it make sense to just have a driver-global TPE?
+            t = Thread(target=err_all_callbacks)
+            t.daemon = True
+            t.start()
+
     def get_request_id(self):
         """
         This must be called while self.lock is held.
diff --git a/tests/unit/test_host_connection_pool.py b/tests/unit/test_host_connection_pool.py
index fec889e9..79391a2a 100644
--- a/tests/unit/test_host_connection_pool.py
+++ b/tests/unit/test_host_connection_pool.py
@@ -184,7 +184,7 @@ class HostConnectionPoolTests(unittest.TestCase):
     def test_return_defunct_connection_on_down_host(self):
         host = Mock(spec=Host, address='ip1')
         session = self.make_session()
-        conn = NonCallableMagicMock(spec=Connection, in_flight=0, is_defunct=False, is_closed=False, max_request_id=100)
+        conn = NonCallableMagicMock(spec=Connection, in_flight=0, is_defunct=False, is_closed=False, max_request_id=100, signaled_error=False)
         session.cluster.connection_factory.return_value = conn
 
         pool = HostConnectionPool(host, HostDistance.LOCAL, session)