This study explored certain leadership methods that eSupervisors were utilizing with eInterns through the theoretical lenses of House’s (1971) path-goal theory of leadership and the effectiveness of these methods on learning outcomes. The overarching research question that guided this study was: How do eSupervisors contribute to the learning growth of eInterns? A qualitative multi-case study was conducted on a population of eSupervisors, current eInterns (students), and past eInterns (graduates) that were associated with the Virtual Student Foreign Service (VSFS) program. VSFS is a program aimed at exposing students to working opportunities in the government. The findings from this study imply that there are a number of ways in which eSupervisors can contribute to the learning growth of eInterns. These contributions will vary depending on the eInterns, the environmental characteristics, the leadership approach taken, and the motivational factors involved. The significance in applying this research today falls in line with the booming growth of distance education programs the trend of incorporating technology in the classrooms.