Qualitative comparative analysis is gradually becoming more established in the evaluation field. The purpose of this article is to highlight the potential for evaluation research of engaging in consecutive rounds of this analysis. This is possible when approaching qualitative comparative analysis as a systematic strategy for configurational theorizing. To substantiate this potential, we present two evaluation studies on Research and Development subsidies for companies in Poland. Compared with the results of the first study, the findings of the subsequent consecutive qualitative comparative analysis studies were much more nuanced and helped in developing a full-fledged configurational program theory. In addition to elaborating on the strengths of a consecutive qualitative comparative analysis approach and the relevance of configurational program theories for evaluators, this article shares the main lessons learned in overcoming challenges common to such designs. Thus, concrete guidance is offered to researchers and evaluators who are willing to take configurational theorizing seriously.