We describe, analyze, and discuss the study, interpretation, and implementation of ongoing educational change that explores the limits of conventional approaches to inquiry driven projects and offers some alternative approaches to engaging change. Using data from a case study of a recent technical assistance project concerned with educational equity for marginalized groups, we detail the challenges of careful inquiry and interpretation in a rapidly changing complex environment that characterizes school systems in the United States (U.S.). In this chapter we suggest that technical assistance offers a critical opportunity to engage individuals and activity systems in changing the outcomes of their practice and, in doing so, shift their praxis in ways that can mediate future work. Because we locate this work within a methodology that is steeped in activity theory, we describe and critique a set of methods for technical assistance that offers a rich context for ongoing research and inquiry as a critical feature for systems transformation.