Operating System fingerprinting is a reconnaissance method which can be used by attackers or forensic investigators. It identifies a system's identity by observing its responses to targeted probes, or by listening on a network and passively observing its network ‘etiquette’. The increased deployment of encrypted tunnels and Virtual Private Networks (VPNs) calls for the formulation of new fingerprinting techniques, and poses the question: “How much information can be gleaned from encrypted tunnels?” This paper investigates IPSec VPN tunnel-establishment and tear-down on three IPSec implementations: Microsoft Windows 2003, Sun Solaris 9 x86, and racoon on Linux 2.6 kernel. By analysing each platform's Internet Key Exchange (IKE) messages, which negotiate the IPSec tunnel, we identify a number of discriminants, and show that each of these platforms can be uniquely identified by them. We also show that the nature of some encrypted traffic can be determined, thus giving the observer an idea of the type of communication that is taking place between the IPSec endpoints.