Despite the introduction of many advanced programming languages and the escalating cost of developing programs in COBOL, development of COBOL source code continues throughout the business community. Eventually, the cost of maintaining this code will be prohibitive. Migrating software systems from COBOL based implementations to modern programming implementations will be necessary. The migration of legacy systems involves some risk which can be mitigated by selection of the appropriate migration strategy. In this thesis, various migration strategies are examined in terms of the risks and benefits of each approach. A methodology for assessing a business domain for the specific purpose of selecting the appropriate strategy is presented. The identified methodology will be demonstrated using the business functions specific to a large complex insurance company. It will be shown that for this specific industry, that reengineering requirements and building a replacement system in-house is superior to implementing a commerical off-the-shelf (COTS) like the Enterprise Resource Planning (ERP) system.