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The World Wide Web and the services it provides are continually evolving. Even for a single time instant, it is a complex task to methodologically determine the infrastructure over which these services are provided and the corresponding effect on user perceived performance. For such tasks, researchers typically rely on active measurements or large numbers of volunteer users. In this paper, we consider an alternative approach, which we refer to as passive crowd-based monitoring. More specifically, we use passively collected proxy logs from a global enterprise to observe differences in the quality of service (QoS) experienced by users on different continents. We also show how this technique can measure properties of the underlying infrastructures of different Web content providers. While some of these properties have been observed using active measurements, we are the first to show that many of these properties (such as location of servers) can be obtained using passive measurements of actual user activity. Passive crowd-based monitoring has the advantages that it does not add any overhead on Web infrastructure, it does not require any specific software on the clients, but still captures the performance and infrastructure observed by actual Web usage.