Consider the perceived risks of migrations that tend to cloud the benefits of new technologies from a business perspective, making it difficult to justify technology migrations to the decision makers in an enterprise. See how these risks can be identified, planned for ahead of time and evaluated against cost, time to market, and other business factors so that the project planner can have a solid handle on the bottom line of a project. See examples from a real-world commercial application and look at each of the business and technological factors that needed to be addressed when migrating an ASP application to ASP.NET on the soon to be released Windows Server 2003.