diff --git a/kdcproxy/__init__.py b/kdcproxy/__init__.py
index 1493b30..f61e867 100644
--- a/kdcproxy/__init__.py
+++ b/kdcproxy/__init__.py
@@ -60,6 +60,11 @@ def __init__(self, code, msg, headers=[]):
     def __str__(self):
         return "%d %s" % (self.code, httplib.responses[self.code])
 
+class SocketException(Exception):
+
+    def __init__(self, message, sock):
+        super(Exception, self).__init__(message)
+        self.sockfno = sock.fileno()
 
 class Application:
     MAX_LENGTH = 128 * 1024
@@ -68,10 +73,23 @@ class Application:
         "udp": socket.SOCK_DGRAM,
     }
 
+    def addr2socktypename(self, addr):
+        ret = None
+        for name in self.SOCKTYPES:
+            if self.SOCKTYPES[name] == addr[1]:
+                ret = name
+                break
+        return ret
+
     def __init__(self):
         self.__resolver = MetaResolver()
 
     def __await_reply(self, pr, rsocks, wsocks, timeout):
+        starting_time = time.time()
+        send_error = None
+        recv_error = None
+        failing_sock = None
+        reactivations = {}
         extra = 0
         read_buffers = {}
         while (timeout + extra) > time.time():
@@ -92,6 +110,9 @@ def __await_reply(self, pr, rsocks, wsocks, timeout):
                     pass
 
             for sock in w:
+                (react_n, react_t) = reactivations.get(sock, (-1, 0.0))
+                if react_t > time.time():
+                    continue
                 try:
                     if self.sock_type(sock) == socket.SOCK_DGRAM:
                         # If we proxy over UDP, remove the 4-byte length
@@ -101,8 +122,13 @@ def __await_reply(self, pr, rsocks, wsocks, timeout):
                         sock.sendall(pr.request)
                         extra = 10  # New connections get 10 extra seconds
                 except Exception as e:
-                    logging.warning("Conection broken while writing (%s)", e)
+                    send_error = e
+                    failing_sock = sock
+                    reactivations[sock] = (react_n + 1,
+                                           time.time() + 2.0**(react_n+1) / 10)
                     continue
+                if sock in reactivations:
+                    del reactivations[sock]
                 rsocks.append(sock)
                 wsocks.remove(sock)
 
@@ -110,7 +136,8 @@ def __await_reply(self, pr, rsocks, wsocks, timeout):
                 try:
                     reply = self.__handle_recv(sock, read_buffers)
                 except Exception as e:
-                    logging.warning("Connection broken while reading (%s)", e)
+                    recv_error = e
+                    failing_sock = sock
                     if self.sock_type(sock) == socket.SOCK_STREAM:
                         # Remove broken TCP socket from readers
                         rsocks.remove(sock)
@@ -118,6 +145,21 @@ def __await_reply(self, pr, rsocks, wsocks, timeout):
                     if reply is not None:
                         return reply
 
+        if reactivations:
+            raise SocketException("Timeout while sending packets after %.2fs "
+                                  "and %d tries: %s" % (
+                                      (timeout + extra) - starting_time,
+                                      sum(map(lambda r: r[0],
+                                              reactivations.values())),
+                                      send_error),
+                                  failing_sock)
+        elif recv_error is not None:
+            raise SocketException("Timeout while receiving packets after "
+                                  "%.2fs: %s" % (
+                                      (timeout + extra) - starting_time,
+                                      recv_error),
+                                  failing_sock)
+
         return None
 
     def __handle_recv(self, sock, read_buffers):
@@ -215,6 +257,7 @@ def __call__(self, env, start_response):
             reply = None
             wsocks = []
             rsocks = []
+            sockfno2addr = {}
             for server in map(urlparse.urlparse, servers):
                 # Enforce valid, supported URIs
                 scheme = server.scheme.lower().split("+", 1)
@@ -261,6 +304,7 @@ def __call__(self, env, start_response):
                                 continue
                         except io.BlockingIOError:
                             pass
+                        sockfno2addr[sock.fileno()] = addr
                         wsocks.append(sock)
 
                     # Resend packets to UDP servers
@@ -271,7 +315,15 @@ def __call__(self, env, start_response):
 
                     # Call select()
                     timeout = time.time() + (15 if addr is None else 2)
-                    reply = self.__await_reply(pr, rsocks, wsocks, timeout)
+                    try:
+                        reply = self.__await_reply(pr, rsocks, wsocks, timeout)
+                    except SocketException as e:
+                        fail_addr = sockfno2addr[e.sockfno]
+                        fail_socktype = self.addr2socktypename(fail_addr)
+                        fail_ip = fail_addr[4][0]
+                        fail_port = fail_addr[4][1]
+                        logging.warning("Exchange with %s:[%s]:%d failed: %s",
+                                        fail_socktype, fail_ip, fail_port, e)
                     if reply is not None:
                         break