This article advances a continuing line of inquiry into the potential of digital educative curriculum materials to support teachers’ development of professional teaching knowledge. Instead of standalone levers of change, the educative curricula in this study were featured resources within a novel professional development approach. The qualitative, design-based research experiment asked, “Can sustained, collaborative professional development experiences with digital educative curriculum materials help in-service social studies teachers develop professional teaching knowledge?” Following a 13-month study, none of the six participants fully adopted the promoted wise practice pedagogy, problem-based historical inquiry. However, findings suggested that sustained, collaborative experiences with digital educative curricula helped teachers in this study begin to articulate and demonstrate tenets of problem-based historical inquiry (e.g., purposeful student-inquiry grounded in recurring societal concerns, structuring classroom events to promote historical thinking). The authors proposed three features to strengthen future teacher-support efforts: dynamic experiences modeling wise practices, digital curriculum designed for collaboration, and expert mentors to help facilitate learning.