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This research aims to understand how design tools for math learning that afford creative exploration can encourage sustained engagement and what effect use of such tools will have for the learner. It explores engagement with the design medium and with the math content in the moment and over an extended period of time. Some goals of this research are to suggest how to encourage sustained interest on the part of the learner, ways in which the craft or design domain and the content should be related to each other, and how software and software tools can support this relationship.Our hypothesis is that a dynamic, constructionist environment used over time that allows exploration of curricular content in an artistic, expressive way, coupled with reflective activity that highlights connections between the expressive and content domains will promote: 1) sustained engagement with the content area, 2) choosing to engage with the expressive medium, and 3) substantial learning in the content area. Support for this hypothesis is being sought by having students use a constructionist software environment for design intermittently for several months in the classroom with the option of using it at home during free time. During that time, we will follow students as their engagement waxes and wanes in the context of us trying to keep them engaged in several ways, e.g., by adding new tools to the software system.This research is based on a constellation of ideas from math learning, constructionism, and design learning, and builds on these foundations in addition to using other closely related research for guidance. It takes suggestions from literature on designing constructionist toolkits that suggest designing learning environments with strong connections to what learners already know, understand, or enjoy so that they can take full advantage of the learning opportunities available to them in the system (e.g., Resnick et al., 1996). Some constructionist research focuses on children finding their "gears" for learning, a medium that drives their passion for finding out new things (e.g., Papert, 1980). This research aims to show how to help some children find their "gears" while offering an accessible learning experience for all the students in the classroom by providing activities and tools that support realization of learning affordances. This research finds support in the literatures on learning through design (e.g., Kafai & Harel 1991; Shaffer, 1997; Kolodner et al., 2003), combining math and craft (e.g., Shaffer, 1996; Eisenberg, 2003), and math learning (e.g., Clements, 1999).