Encrypted protocols, such as SSL, are becoming more prevalent because of the growing use of e-commerce, anonymity services, and secure authentication. Likewise, traffic analysis is becoming more common because it is often the only way to analyze these protocols. Though there are many valid uses for traffic analysis (such as network policy enforcement and intrusion detection), it can also be used to maliciously compromise the secrecy or privacy of a user. While the payload can be strongly protected by encryption, analysis of traffic patterns can yield information about the type and nature of traffic. In this paper we use simulation and an analytic model to examine the impact on user experience of a scheme that masks the behavior of real traffic by embedding it in synthetic, encrypted, cover traffic. This point provides a novel context where we observe the synergy of simulation and analytic modeling. We show that a detailed simulation model of network traffic characteristics can be used to estimate the parameters of an analytic model of tunneling.