Two strategies that have significantly changed the way we conventionally think about managing software development and sustainment are the family of development approaches collectively referred to as agile methods, and the distribution of development efforts on a global scale. When you combine the two strategies, organizations have to address not only the technical challenges that arise from introducing new ways of working, but more importantly have to manage the 'soft' factors that if ignored lead to hard challenges. Using two case studies of distributed agile software development in India we illustrate the areas that organizations need to be aware of when transitioning work to India. The key issues that we emphasize are the need to recruit and retain personnel; the importance of teaching, mentoring and coaching; the need to manage customer expectations; the criticality of well-articulated senior leadership vision and commitment; and the reality of operating in a heterogeneous process environment.