This paper examines the evolution of the boundary-spanning role of the school superintendent and its impact on their ability to function effectively as educational leaders. This role, which is a relatively new development in the definition of superintendency, includes acting as a filtering agent controlling the flow of information in and out of the open and permeable boundary between the school system, the board of education, and the community. The various activities associated with boundary-spanning are also significant sources of stress. Literature on the superintendency reveals boundary-spanning to be a major challenge to the position. To study the impact of boundary-spanning on the role of superintendent, 149 Connecticut superintendents were surveyed via a mailed questionnaire, of which 109 produced usable returns. Data were analyzed qualitatively to determine types of major stressors and frequencies of incidence of each type. Sources of stress include politics, gaining support for budget, public criticism and expectations, the challenge of student achievement, negative press coverage, and the personal and professional toll generated by a heavy workload. The primary recommendation, which holds policy implications, is the need to reexamine the position of school superintendent, paying particular attention to the boundary-spanning role. (Contains 29 references.) (RT)