Early in my PhD training, I became involved with evaluating an intervention aimed at linking and retaining young, racial and ethnic minority men who have sex with men who were living with HIV into medical care. This intervention, ‘Strength Through Youth Livin’ Empowered', was a multicomponent program that was carried out over 3 years. This case study details my experience coming into the project as it was concluding and being asked to conduct the quantitative evaluation. I draw attention to the process by which we came to the decisions ultimately represented in the published journal article. Of particular note, I focus on defining the scope of the evaluation, operationalizing our primary outcome of retention, constructing an appropriate comparison group, and describing the steps that go into analysis. By going through each of these steps, I highlight both conceptual issues and pragmatic considerations that can influence the evaluation process. Using my experience as an example, this case study guides graduate students and other new researchers about how to navigate the disconnect between in-classroom education and on-the-ground realities of evaluation research.