Formal mentoring has been an effective approach to mitigate challenges facing underserved youth and contributes to observable improvements in behavior, relationships, and emotional well-being. In recent years, virtual mentoring has emerged as a promising way to expand the provision of mentoring. By engaging virtually, mentorship programs can mitigate typical challenges of travel time and distance between mentor and mentee. Nonetheless, there are also challenges associated with virtual mentoring, including the potential for miscommunication and possible difficulties developing deep connections. In 2020, the U.S. Dream Academy began developing and implementing virtual and hybrid mentoring services to explore the benefits and address the challenges of virtual mentoring. As the coronavirus disease 2019 (COVID-19) pandemic caused widespread disruption in schooling in the United States, the U.S. Dream Academy leveraged this unique opportunity to begin implementing virtual mentoring. This report describes how the U.S. Dream Academy sought to expand its mentoring program to include a virtual option. The authors summarize the development and implementation of the mentoring program and lessons learned from this experience with the goal of supporting program improvement. This report may also assist other mentoring programs that seek to adopt a similar mentoring model. [The research for this report was sponsored by U.S. Dream Academy.]