This descriptive case study includes both new principals and their mentor principals engaged in e-mentoring activities. This study examines the components of a school district's mentoring program in order to make sense of e-mentoring technology. The literature review highlights mentoring practices in education, and also draws upon e-mentoring research in the fields of business and healthcare. This is an innovative study because the use of e-mentoring technology for principal support and development is unexplored. Senge's (1990) learning organization serves as a theoretical foundation, focusing this study by recognizing that the success of a principal is tied to the success of the principal's school. The development of a case study protocol ensured thorough analysis of the five sources of data collected: 1) documentation; 2) archival records; 3) interviews; 4) direct observations; and 5) physical artifacts (Yin, 1994; 2009). Findings included eight elements that impact e-mentoring: 1) background knowledge and experience of the participants; 2) technology experience of the participants; 3) job-related duties and responsibilities of the participants; 4) goals and aims of the e-mentoring program; 5) content of the e-mentoring conversations; 6) technology training provided to participants; 7) synchronous or asynchronous nature of the technology involved; and 8) support for multiple mentors and mentees. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]