Research on the relationship between play and early literacy flourished in the 1990s but slowed to a trickle at the start of the new millennium. As we see it, play—literacy research is stuck in a theoretical and methodological rut. Two promising conceptual frameworks — connectionist and dynamic systems theories — can supply the thrust needed to get this important area of research moving forward again. We give examples of how Fischer’s dynamic skill theory provides analytic tools for examining data on play and literacy, including partially ordered scaling of items (POSI), dynamic modeling, and dynamic assessment. These new tools and theoretical lenses have the potential to answer the essential question: Does play make a difference in early literacy development?