Summary: Web cost estimation models and productivity analysis reports help project managers allocate resources more adequately, control costs, schedule and improve current practices, leading to projects that are finished on time and within budget. Therefore this chapter has two main objectives. The first is to introduce the concepts related to Web cost estimation \& Web applications’ sizing and present a case study where a real Web cost model is built; the second is to introduce the concepts of productivity measurement \& benchmarking, and to also present a case study on productivity benchmarking.