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IPSec over TCP fails when traffic flows through ASA




Cisco  VPN Clients that connect to a VPN headend using IPSec over TCP might  connect to the headend just fine, but then after some time the  connection will fail. For this specific problem, switching to IPSec over  UDP or native ESP IPSec encapsulation will work just fine.



To  encounter this specific problem, Cisco VPN Clients must be configured  to connect to a VPN headend device using IPSec over TCP. Most commonly,  we see network administrators configure the ASA to accept Cisco VPN  Client connections over TCP Port 10000.



When  the VPN client is configured for IPSec over TCP (known as cTCP) the VPN  client software will not respond if a duplicate TCP ACK is received  asking for the VPN client to re-transmit data. A duplicate ACK might be  generated if there is packet loss somewhere between the VPN client and  the ASA headend; intermittent packet loss is a fairly common reality on  the internet. However, since the VPN endpoints are not using the TCP  protocol (remember they're using cTCP), the endpoints will continue  transmitting and the connection will continue.

A problem is only seen in this scenario if there is another  device such as a firewall tracking the TCP connection statefully. Since  the cTCP protocol does not fully implement a TCP client, and server  duplicate ACKs will not be responded to, this can cause other devices  in-line with this network stream to drop the TCP traffic. Packet loss  must occur on the network causing TCP segments to go missing, which  triggers the problem.


This isn't a bug, but a side effect of packet loss on the network,  and the fact that cTCP is not real TCP. cTCP tries to emulate the TCP  protocol by wrapping the IPSec packets within a TCP header, but that is  the extent of the protocol.


This issue occurs usually when network administrators implement  a ASA with an IPS, or do some sort of application inspection on the ASA  that causes the firewall to act as a full TCP proxy of the connection.  If there is packet loss, the ASA will ack for the missing data on behalf  of the cTCP server or client, but the vpn client will never respond;  since the ASA never receives the data it is expecting, communication  cannot continue, causing the connection to fail.



To resolve this problem, any of the following can be done:

  1. Switch from IPSec over TCP to IPSec over UDP, or native encapsulation with the ESP protocol.
  2. Switch to the AnyConnect client for VPN termination, which uses a fully implemented TCP protocol stack.
  3. Configure the ASA to apply tcp-state-bypass for these specific  IPSec/TCP flows. This essentially disables all security checks for the  connections that match the tcp-state-bypass policy, but will allow the  connections to work until another resolution from this list can be  implemented. More information on this feature can be found in the  configuration guide:
   4.  Identify the source of the packet loss, and take corrective action  to prevent the IPSec/TCP packets from being dropped on the network. This  is usually impossible or extremely difficult since the trigger to the  issue is usually packet loss on the internet, and the drops cannot be  prevented.
This document was created by Jay Johnston (
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