The authors argue that hitherto separate methodological conversations about abduction and comparison can be fruitfully brought together to generate novel, well-founded insights and retheorize an object of study in multiple-case qualitative inquiry. The authors call this abductive cross-case comparison and illustrate it by way of a collective study of how professional boundary work is changing under transnational conditions. In this study, the authors faced a common challenge in qualitative-comparative research: what to do when initial observations generate “surprises” that seem to confound the theoretical frameworks undergirding the comparison? To discuss how abductive inferences supported the authors’ response to this challenge, they explicate the acts of discovery and (re)conceptualization involved through various steps in a team-based research process. Building on the existing qualitative comparison literature, the authors suggest that such procedures fill a methodological gap and may hold great promise for overcoming obstacles in designing and implementing comparative research. Overall, the authors explicate and illustrate the method of abductive cross-case comparison, including their work as a research team. The aim of this article is thus to help sociologists implement better qualitative research that leverages a fuller potential of comparative designs to push beyond established knowledge and frameworks.