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This article describes the use of developmental evaluation as applied to countering violent extremism (CVE) programs. It discusses the application of this method to an evaluation of the Boston CVE Pilot Program, with specific attention given to two CVE initiatives that were awarded pilot grants and volunteered to be evaluated. Developmental evaluation is an inherently iterative engagement that requires a continuous exchange between the parties designing the initiative and the parties evaluating it (the evaluation, in short, is not merely a post hoc engagement). We present the results of the evaluations using qualitative and quantitative data. The conclusion points to lessons learned in the application of a developmental evaluation framework: an assessment of the viability, utility, and benefits of utilizing such an approach to assess the impact of CVE programs (versus a traditional evaluation rubric. It also discusses the limitations that an outside organization engaged in this evaluative work might face.