The efficient transportation of elementary and high school students within the United States has long been of interest to academics and practitioners alike. Research in the field has closely followed the development of solution techniques to general network routing problems by appropriately altering these models and the associated algorithms to address the subtleties of a particular bus routing problem. In this paper, a mathematical model that accommodates many of the sources and impacts of uncertainty is presented. Due to the impact of time windows on routing, traditional solution heuristics are unsuitable. However, a number of regular stochastic events that arise in the design and operation of pupil transportation are discussed and general solution outlines are presented.