This chapter presents and reflects on twenty years of personal experience working with the Adventist Development and Relief Agency (ADRA), and explores development across faith boundaries with two primary objectives. First, and most importantly, this chapter documents personal and organisational learnings about development across faith boundaries through critical selfreflection in a series of interwoven case studies. Second, exploring these case studies, it analyses experiences and draws out insights into factors that caused issues and enabled successful development work in interfaith contexts. Some proposed practical frameworks for intentionally making the practice of development across faith boundaries more effective are briefly explored. It is proposed that the application of both personal and professional practices to enhance empathy and to establish and maintain trust is essential to the achievement of successful development outcomes in interfaith collaborations. This can be explained in terms of building foundations around shared faith values. It must be noted at this point that the case studies presented reflect a distinctly personal and therefore necessarily subjective experience of working in development across faith boundaries. It is therefore important to ground the following case studies in some brief background on both ADRA and the author. Consistent with the qualitative research approaches advocated by Ratner (2002) when dealing with subjectivity, the validity of conclusions reached in this chapter must ultimately be judged against the actual behaviour exhibited by people working in development across faith boundaries. ADRA is the global humanitarian and development agency of the SeventhDay Adventist (SDA) Church. As such it is a Christian denominationally based, faith-inspired, not-for-profit development organisation. In seeking to demonstrate God’s love and compassion, ADRA works with people in poverty and distress to create just and positive change through empowering partnerships and responsible action. While, as will be seen in the case studies that follow, membership of the SDA Church is not a requirement to work for ADRA, I am a baptised member of the SDA Church. It is also important to recognise that the SDA Church, which is highly evangelical and invests heavily in evangelistic activity, has established ADRA with a clear charter to avoid proselytisation entirely in its development and humanitarian work.