Training mentored youth and their caregivers to work together successfully with their mentor and mentoring program is critically important for achieving a safe, high-quality, sustained mentoring relationship, and for obtaining positive youth outcomes. Training for mentees and their caregivers is considered a best practice in the field of mentoring; however, many programs struggle to provide them with systemic and adequate training experiences. This may explain the challenges that some mentors report in their relations with the caregivers of their mentees, which include communication breakdowns, unexpected termination of the relationship, boundary violations, and misuse of power. Training in these areas can provide families with the skills, knowledge, and cognitions needed to develop a strong relationship with their mentor and mentoring program staff members. Given the negative impact of prematurely terminated relationships, programs report a great need for figuring out ways to sustain and support mentoring relationships, and training mentees and their caregivers is one critically important strategy. Through advances in mobile technology and the rise of internet and mobile technology use, there now exists an opportunity to provide innovative and accessible web and mobile-based training resources for parents and youth across the country, including those living in rural areas. The overall goal of the proposed project is to use an iterative proces to develop training for mentees and their caregivers that is accessible via Internet, tablet, and smartphone devices. The finished project will include a multimedia, interactive course designed for family members to complete together. The course content will address topics such as defining mentoring, explaining the importance of training, the benefits of mentoring, common motivations and expectations for mentoring, roles of everyone involved in a mentoring relationship, child safety and boundaries issues, and preparing for the first match meeting. Caregivers and mentees will be able to utilize downloadable tip sheets to help guide conversations with the mentor and mentoring program staff. A complete set of mobile applications for mentees and caregivers to use in training are planned for development. Commercialization of the proposed product will be facilitated through our connections with leaders in the field of youth mentoring and the rising demand from the field for this type of resource. In Phase I, three focus groups will be conducted with mentors, mentees, and their caregivers. They will provide feedback on program content and methods. A One-to-One Evaluation study with five mentee/caregiver dyads will provide feedback on program usability and consumer satisfaction. Finally, a Feasibility Study will be conducted to examine the short-term effectiveness of the training for mentees and caregivers for improving their attitudes and knowledge regarding preparing for a mentoring relationship and to obtain consumer satisfaction feedback.