Masquerade: How a Helpful Man-in-the-Middle Can Help You Evade Monitoring. presented at defcon 2014

by Ryan Lackey, The Grugq, Marc Rogers,

Summary : Sometimes, hiding the existence of a communication is as important as hiding the contents of that communication. While simple network tunneling such as Tor or a VPN can keep the contents of communications confidential, under active network monitoring or a restrictive IDS such tunnels are red flags which can subject the user to extreme scrutiny.Format-Transforming Encryption (FTE) can be used to tunnel traffic within otherwise innocuous protocols, keeping both the contents and existence of the sensitive traffic hidden.
However, more advanced automated intrusion detection, or moderately sophisticated manual inspection, raise other red flags when a host reporting to be a laser printer starts browsing the web or opening IM sessions, or when a machine which appears to be a Mac laptop sends network traffic using Windows-specific network settings.
We present Masquerade: a system which combines FTE and host OS profile selection to allow the user to emulate a user-selected operating system and application-set in network traffic and settings, evading both automated detection and frustrating after-the-fact analysis.