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This paper analyzes web server performance under simulated WAN conditions. The workload simulates many critical network characteristics, such as network delay, bandwidth limit for client connections, and small MTU sizes to dial-up clients. A novel aspect of this study is the examination of the internal behavior of the web server at the network protocol stack and the device driver. We discovered that WAN network characteristics may significantly change the behavior of the web server compared to LAN-based simulations and may make many of optimizations of server design irrelevant in this environment. Particularly, we found that the small MTU size of the dial-up or wireless user connections can increase the processing overhead several times.