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Teaching mathematics ambitiously has received increased attention. In this paper, we argue that to materialize this vision in contemporary classes, we need to understand how practicing teachers experiment with certain aspects of this teaching and what challenges they encounter. Toward this end, focusing on one aspect of teaching ambitiously—designing and using enablers and extenders—we follow four elementary schoolteachers’ experimentation during a video-club program. Drawing on a rich corpus of data and looking across the four cases, we sketch the changes these teachers introduced in their work and the challenges they faced. This mapping of changes and challenges can inform professional development attempts to support practicing teachers while attempting to engage all their students in mathematically challenging work.