This chapter discusses the evaluation of an urban schoolto-career intervention program using a culturally responsive approach, highlighting the successes and challenges experienced during the design and implementation of the study.Program evaluation has long been used to reveal program characteristics, merits, and challenges. While providing information about program effectiveness, evaluations can also ensure understanding of program outcomes, efficiency, and quality. Furthermore, evaluations can analyze and examine a program's political and social environment as well as appraise the achievement of its goals, objectives, impact, and costs (Posavac and Carey, 2003). Another important factor in conducting evaluations is their cultural responsiveness. Consideration of this factor seems quite obvious, but in our opinion remains uncommon.In the United States, numerous programs in various settings are having an effect on individuals of all types. Within the past three decades, there have been shifts to identify and meet program needs of these diverse populations and to make evaluations more inclusive of all cultures. This shift has helped in documenting program processes, effectiveness, and outcomes, as well as providing specific benefits to projects and their stakeholders.