To what extent do divided cities characterized by geopolitical conflicts and a variety of contradictory expectations create a distinctive context and a unique professional conflict for individuals holding boundary-spanning roles? Data collected in a set of in-depth interviews conducted with school principals leading Arab schools located in East Jerusalem provide evidence for principals' stress following the large and various number of role expectations they are expected to satisfy. The data testify to principals' exposure to a hybrid role conflict--a unique conflict reflecting a mixture of incongruent expectations regarding a particular issue coming from both internal and external sources representing different sets of values. Moreover, it is evident that hybrid conflicts suggesting a clash between competing values and ideologies foster principals' tendency to employ a radical coping strategy based on a cost-benefit minimal risk approach and to act deceitfully as means to diminish their stress. The study demonstrates the significance of contextual features that frame the scope for individuals' professional behavior when serving in boundary-spanning roles and discusses some implications of hybrid conflicts for professional judgment and behavior.