Lower-income students with outstanding academic credentials often lack the knowledge and support to apply to highly ranked colleges and universities that they would be eligible to attend. This study investigated a national e-mentoring program, CollegePoint, that provided one-to-one mentoring to low- and moderate-income, high-achieving high school students. The 15-month mentoring program covered college choice, application, and financial aid processes. We employed a human ecology theoretical framework that highlights interactions among mentoring experiences, individual characteristics, and multiple environmental contexts. Results of 13 focus groups with e-mentors and interviews with 123 student participants and 8 project directors indicated that the virtual mentoring format was comfortable and often preferable to students. The remote mode of communication allowed for considerable variation in engagement, however, with some students consistently in contact with their mentors and others dropping out temporarily or permanently. Students who remained highly engaged with their mentors were those who needed help, felt a connection to their mentor, and appreciated the arms-length relationship enabled by the virtual format. For these students, e-mentoring gave them a realistic sense of their eligibility for admission to a range of selective colleges and helped them complete time-sensitive tasks and make thoughtful decisions. Consonant with ecological theory, CollegePoint appeared to act as a bridge between students' immediate contexts and the policies, structures, and procedures related to college admissions and financial aid. When e-mentors were able to engage all aspects of students' ecology, CollegePoint had the potential to transform the college application experience and even the self-concept of students.