HOWTO: Unauthenticated Opportunistic IPsec

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Classic VPNs provide encryption and authentication of hosts or users based on an existing and configured relationship. This can be an enterprise VPN, or a VPN service provider.

The goal of Opportunistic IPsec is to attempt to encrypt ALL communications between any two host without requiring a trust relationship or preconfiguration. That is, the goal is to encrypt the entire internet.


# install libreswan-3.19 or higher using apt-get, yum or dnf
cd /etc/ipsec.d
ipsec restart
# test by pinging a known Opportunistic IPsec site:
ipsec whack --trafficstatus

How does Opportunistic IPsec work?

The IKEv2 protocol is used to negotiate the symmetric encryption keys for the IPsec subsystem in the kernel. The kernel then takes care of encrypting and decrypting the traffic between the hosts.

The IKE daemon is responsible for this negotiation. It uses encryption itself to protect the IKE communication between the hosts. Therefor, IKE communication consists roughly of two parts:

  • Setup a secure communication link to the other host
  • Mutually agree on encryption keys and source/destination IP addresses to install in the kernel.

To setup a secure channel, the IKE protocol first performs a DiffieHellman Key Exchange. Then the peers authenticate each other. Once authenticated, symmetric keys for the kernel are derived.

The IKE daemon can also tell the kernel which traffic it wants to be notified for, so it can initiate IKE. For Opportunistic IPsec, the libreswan IKE daemon basically tells the kernel it is interested in all traffic. Once traffic for a new IP is received or ready to be sent, the kernel will inform the IKE daemon. The IKE daemon will attempt to setup an IPsec tunnel. If that is not possible, for instance because the other end does not support Opportunistic IPsec, the IKE daemon tells the kernel to let that traffic go unencrypted. The IKE daemon manages the established tunnels and cleartext passes. It will keep active IPsec tunnels alive and terminate idle IPsec tunnels. It also expires the cleartext passes to try and upgrade those to IPsec tunnels as well.

The biggest issue is how to authenticate someone you never communicated with before. And IKE/IPsec in the past required both parties to identify itself. However, as of IKEv2 and specifically since [ RFC-7619[, the IKE protocol allows a special NULL authentication. We use this to provide different levels of authentication and protection

Opportunistic IPsec is always host-to-host, meaning IPsec tunnels are only setup for the hosts themselves. Since there is no method to securely convey ownership of a certain IP address, an Opportunistic IPsec host can never be trusted to talk on another IP's behalf.

Types of Opportunistic Encryption

  • Mutually authenticated IPsec - this requires both peers authenticate each other. This is the classic IPsec model. Authentication could be based on X.509, Kerberos, DNSSEC or a bitcoin ledger.
  • Single side authentication - this requires that the client authenticates the server, but the server allows everyone to connect and encrypt. This is similar to the SSL/TLS model
  • Unauthenticated encryption - this requires no authentication from either side. But it is vulnerable to a Man In The Middle attack.

Work is being done to implement all three types of Opportunistic IPsec. As of version 3.16, libreswan supports unauthenticated encryption.

Configuring Opportunistic unauthenticated IPsec

To configure libreswan, simply download the configuration file oe-upgrade-authnull.conf and place it in the /etc/ipsec.d directory.

You can tune for which IP ranges you want to try Opportunistic IPsec. You can configure these ranges to be passive or active. Passive means the system will respond and accept IKE requests for IPsec, but it will never attempt to initiate it. This can be used on busy servers where it is expected that only few clients connecting to it will support Opportunistic IPsec. Active means that the system will always attempt to initiate IKE.

The passive IP ranges are configured in /etc/ipsec.d/policies/clear-or-private

The active IP ranges are configuref in /etc/ipsec.d/private-or-clear.

Per default, is places in the active range.

Simply restart libreswan and Opportunistic IPsec will be enabled.

Monitoring the sytem for IPsec tunnels

There are three important commands to get information about IPsec tunnels and Shunts. Shunts are placed in the kernel to allow cleartext, once the IKE daemon determined it cannot setup IPsec.

  • ipsec whack --trafficstatus

This will show the active IPsec tunnels

  • ipsec whack --shuntstatus

This will show the active shunts. The ones labeled "acquire" are currently in an IKE negotiation. The ones labeled "oe-failing" are shunts installed due to IKE failures.

  • ipsec status

This will give a lot of developer specific internal status of the IKE daemon.

Test hosts

If you want to test Opportunistic IPsec, you can do so by sending traffic to any * or * host. If you browse to it will inform you whether or not your connection has been encrypted with Opportunistic IPsec.

Below follows an example output from the commandline:

[root@oe1 ~]# ipsec whack --trafficstatus
006 #3225: "private-or-clear#"[2] ..., type=ESP,  add_time=1450417506, inBytes=252, outBytes=252, id='ID_NULL'
006 #3229: "private-or-clear#"[4] ..., type=ESP,  add_time=1450417537, inBytes=252, outBytes=252, id='ID_NULL'
006 #3234: "private-or-clear#"[774] ..., type=ESP,  add_time=1450417774, inBytes=0, outBytes=0, id='ID_NULL'
[root@oe1 ~]# ping -c 2
PING ( 56(84) bytes of data.
64 bytes from ( icmp_seq=2 ttl=64 time=25.1 ms
64 bytes from ( icmp_seq=3 ttl=64 time=25.2 ms
--- ping statistics ---
4 packets transmitted, 2 received, 50% packet loss, time 3002ms
rtt min/avg/max/mdev = 25.161/25.185/25.210/0.160 ms
[root@oe1 ~]# ipsec whack --trafficstatus
006 #3238: "clear-or-private#"[2] ..., type=ESP,  add_time=1450417921, inBytes=252, outBytes=252, id='ID_NULL'
006 #3225: "private-or-clear#"[2] ..., type=ESP,  add_time=1450417506, inBytes=252, outBytes=252, id='ID_NULL'
006 #3229: "private-or-clear#"[4] ..., type=ESP,  add_time=1450417537, inBytes=252, outBytes=252, id='ID_NULL'
006 #3236: "private-or-clear#"[775] ..., type=ESP,  add_time=1450417894, inBytes=0, outBytes=0, id='ID_NULL'

[root@oe1 ~]# ipsec whack --shuntstatus
000 Bare Shunt list:
000 -0-> => %pass 0    oe-failing