Over the past few years, there has been significant interest in content-aware routing that use the information found in the payload of packets to provide intelligent request distribution. As these content-aware routing mechanisms have become an increasingly important building block for Internet service providers, the network behavior and effectiveness of such mechanisms are unclear. In this paper we analyze the network dynamic of a busy Web site with the content-aware routing mechanism. We find that some unique characteristics of Web traffic may limit the effectiveness of the content-aware switching. Based on these observations, we also propose solutions to remedy these deficiencies.