In recent years, underserved communities have received much attention within the field of positive youth development (PYD). While there are an increasing number of opportunities for underserved youth to join PYD-based programs, there is growing concern surrounding the lack of critical evaluation of these programs (Kidd, 2008). Unfortunately, there are numerous challenges related to evaluation within underserved communities and in international settings that often prevent or disrupt the research process. These challenges include difficulty building trust with the target population, power relations, obtaining parental consent, demonstrating cultural competence, and attrition. Moreover, these challenges are rarely discussed in the literature (Knight, Roosa, & Umaña-Taylor, 2009). The primary goal of this article is to present an open discussion of such challenges using case studies from four distinct programs implemented with four different underserved communities. In addition, the limited empirical evidence regarding these challenges is presented, along with potential solutions for consideration in future research efforts.