The aim of this study is to demonstrate the challenges encountered in youth participatory evaluation and how digital technology may assist in overcoming these challenges. The study explores the meaning of youth participatory evaluation and examines the challenges faced in utilizing the approach. We argue that using digital technology can help overcome many challenges of youth participatory evaluations, with the added benefit that such technology may also attract and influence young people to engage more fully with evaluation processes. These findings show that digital technology helps decrease adultism, increase adults’ capacity to engage with youth, and respond to and empower youth. Some practical guidelines and challenges are also discussed.