A chain is always as strong as its weakest link. All agile and adaptive organization initiatives need to continuously keep a comprehensive view across markets, targets, organization, processes, people, and technology. An important area is legacy IT modernization. Alongside a real-life client situation, the modernization journey of a custom-build application stack is described. Aspects like enterprise architecture, security, governance and standardization/harmonization beyond pure IT play an important role to ultimately lead to a high-quality market evaluation and the very focused service partner selection.  In this session we will discuss contextualizing the modernization of legacy apps to understand key success factors,  learn from real-time examples, best practice customized approaches, key challenges along with solutions to it.