Today, companies face numerous obstacles in their organizational architectures. Outdated legacy information systems (LIS) and ever-changing business operations are the main drivers for organizations to modernize (Syntel, 2008). Some of the key concerns raised in the 2008 NASCIO national survey of legacy systems were limited or unavailable software maintenance/updates, inability to improve or alter applications, limited knowledge of legacy application tools, non-existent documentation, and ability to enrich or modify security measures. (NASCIO, 2008). Modernizing or replacing legacy systems has resulted in reduced expenses and risks. However, these benefits are not achieved without understanding and selecting an appropriate migration strategy. This research has two objectives: to analyze information security risks associated with legacy systems and to evaluate various types of migration strategies or systems used to modernize legacy systems. systems. Research topics covered include an evaluation of migration strategies used to modernize legacy systems, a comparison of legacy IT and IS architectures and systems deployed at OMH with Farm Family Insurance, a taxonomy of control systems or architectures used to replace legacy systems at OMH, and strategies used to modernize systems by improving functionality and IS. Positive Experiences One of the key benefits of migration is that it provides the opportunity to move critical, antiquated applications to modern technologies (NASCIO, 2008). Migration enriches and safeguards a company's long-standing investment in software infrastructure and efficiently reduces total cost of ownership (...... half of paper...... ges, obsolete IT systems and fluctuating business processes, require proactive solutions (Syntel, 2008). Migration enables the revitalization of current business processes which present opportunities offered by current and future technologies (Bass, 2013). 2013). Any new system must govern process knowledge through a combination of progressive technologies, industry knowledge and Six Sigma methodologies (Torzewski, 2009). inactivity (Torzewski, 2009). Furthermore, the system should comply with open industry standards (Torzewski, 2009).