The purpose of this study was to investigate linkages between students mathematical play, affective experiences, and cognition. The study was conducted in the researchers seventh grade mathematics course. Students experience with school mathematics changed when they entered a course driven by problems and requiring articulation of mathematical reasoning in support of assertions and solutions. In an effort to mediate the transition a variety of non-standard pedagogical approaches were incorporated. Under investigation in this study was the influence technology tools providing a microworld governed by mathematical rules, The Geometers Sketchpad and Microsoft Excel, had in provoking a students engagement, playful activity, and its influence on a students affective experience. The data is largely drawn from four students created files and video recordings of experiences solving problems over a two-month period. Using student expression of emotional experience to focus the analysis of their engagement, this study offers insight into the influence of affective experience during engagement with school mathematics. Results suggest technology tools can provide students opportunities to engage in a broader range of activities playfully. These opportunities to play promoted affective experience, which supported continued engagement with problem solving and the learning of significant mathematics. Further conclusions link a students goal orientation to the nature of their playful activity. Implications for student mathematics learning, teaching practices, the incorporation of technology tools, and student motivation to engage in school mathematics are offered.