This chapter addresses some key challenges facing CIOs and information technology managers including web-based testing and capacity planning in a rapidly changing Internet environment. Determining the testing scope is critical to the success of a web-based testing project. Utilizing typical client-server testing approaches will not address the many added complexities resulting from a web-based system. The requirement for much quicker development and testing cycles has led to the creation of sophisticated software quality tools that automate many of the test types. Effective performance testing is difficult without an accurate depiction of loads. The ability of an organization to effectively prioritize the components requiring testing and to rapidly execute the tests is a requirement in a competitive e-marketplace. Based on the testing scope, the testing organization needs to plan the testing phase, including the types and timing of tests to be performed in both the pre- and post-release stages.