Web Systems are widely used and accepted due to their advantages over traditional desktop applications. Modernization of existing non-Web software towards the Web, however, is a complex and challenging task due to Legacy System characteristics. Independent Software Vendors are struggling to commence Web Migration because of the involved effort and risk. The Agile Web Migration for SMEs (AWSM) approach addresses shortcomings of existing research concerning dedicated support for the initial phase and feasibility with limited resources and expertise. Three novel Web Migration strategies for reverse engineering, risk management and customer impact control developed in the context of an research collaboration with a leading German eHealth Software Vendor, are proposed. In this talk, the effort and risk concerns of Web Migration will be detailed, the main contributions of AWSM presented, results from experiments integrating empirical user studies and quantitative measurements discussed, and a comparison to state-of-the-art Web Migration approaches will be made.