The purpose of this study was to determine the quality of an e-mentoring program and the impact of participation on at-risk high school students enrolled in dropout prevention programs. The quality of the program was evaluated based on the ease of implementation, use of technology, and overall satisfaction. Indicators of student's self-esteem, career decision, attendance, and GED test scores were used to gauge the impact of participation. Design-based research methods were used to compare the participation of students in mentored and control groups. The results indicated a high level of satisfaction with ease of implementation, use of technology, and overall program quality. However, there were no significant differences between the mentored and control groups regarding self-esteem, career indecision, attendance, and GED test scores. Since the GED dropout prevention program provides guidance and mentorship by the coordinator, further research is suggested to account for the role of program and other contributing variables. Also, further research is suggested on the ancillary benefits of e-mentoring.