The purpose of this qualitative narrative study was to examine the sources of stress experienced by urban high school principals and to explore the extent to which stress factors contribute to sustainable leadership practices. The study also sought to provide insight into what urban high school principals perceive as being most supportive and helpful to them with regard to alleviating identified stress factors, thus allowing them to successfully fulfill their daily duties and responsibilities, and promote sustainability. In order to gain an in-depth and behind-the-scenes view of four urban high school principals, a narrative research design was selected. The study used in-depth semi-structured interviews as the method for gathering data from four DRG I Connecticut high school principals. The results of this study support seven policy recommendations to support Connecticut's urban high school principals: (a) Cultivate urban school leaders from within; (b) Provide formal mentoring and ongoing professional development for urban principals and their successors; (c) Embed a community component into the job description of urban principals; (d) Provide urban administrators greater autonomy for selecting their administrative teams; (e) Provide incentives for aspiring urban principals; (f) Align the model for measuring schoolwide growth and success with principles of sustainability; and (g) Redefine the role of head principal. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]