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. Another important factor in conducting evaluations is their cultural responsiveness. 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. Within the domain of education, of particular interest today are evaluations of programs situated in different settings, including urban settings. For these settings, one can ask questions such as: How useful and valid are identified program outcomes? How can staff design evaluations to ensure all stakeholders feel empowered and part of the evaluation process? How can evaluators include the context and culture of program participants during the evaluation process? Since traditional evaluation models cannot easily answer these questions, evaluation research needs to be extended to focus on the range of evidence available through other nontraditional evaluation models. This article explores some of the successes and challenges encountered in evaluating a Howard University Center for Research on the Education of Students Placed At Risk (CRESPAR) urban school-to-career intervention program using a culturally responsive approach.