Thesis (Ph.D.)--Boston University / PLEASE NOTE: Boston University Libraries did not receive an Authorization To Manage form for this thesis or dissertation. It is therefore not openly accessible, though it may be available by request. If you are the author or principal advisor of this work and would like to request open access for it, please contact us at open-help@bu.edu. Thank you. / The size, diversity and continued growth of the World Wide Web combine to make its understanding difficult even at the most basic levels. The focus of our work is in developing novel methods for measuring and analyzing the Web which lead to a deeper understanding of its performance. We describe a methodology and a distributed infrastructure for taking measurements in both the network and end-hosts. The first unique characteristic of the infrastructure is our ability to generate requests at our Web server which closely imitate actual users. This ability is based on detailed analysis of Web client behavior and the creation of the Scalable URL Request Generator (SURGE) tool. SURGE provides us with the flexibility to test different aspects of Web performance. We demonstrate this flexibility in an evaluation of the 1.0 and 1.1 versions of the Hyper Text Transfer Protocol. The second unique aspect of our approach is that we analyze the details of Web transactions by applying critical path analysis (CPA). CPA enables us to precisely decompose latency in Web transactions into propagation delay, network variation, server delay, client delay and packet loss delays. We present analysis of pe1formance data collected in our infrastructure. Our results show that our methods can expose surprising behavior in Web servers, and can yield considerable insight into the causes of delay variability in Web transactions. / 2031-01-01