The process of designing technological systems for the developing world is a challenging task. In a project that we undertook in the summer of 2007 using an iterative design process, we attempted to develop delay-tolerant networking technology on mobile phones to support workers at AIDS orphanages in Zambia and South Africa. Despite extensive preparations and research, we found that conditions on the ground were radically different from what we had anticipated, and we had to quickly re-group and redefine our strategic goals. This experience made us realize that, for this type of design, resiliency and contingency planning were the most valuable tools in our interaction design toolbox. In response to changing conditions, we rapidly prototyped a different mobile telephony application called Nomatic*AID that provides a feedback loop among donors, non-governmental organizations (NGOs), and field workers. In this paper, we reflect on the redirection of our work once we reached our field site and our resulting acceptance of design blind spots. We present lessons we learned to help practitioners meet their goals in the presence of considerable and obvious design distance.