A software tool is created with the hope of providing a journey into a connective, relevant, and meaningful way of knowing in and through the study of art. In this article, the author describes a research project that resulted from unfettered imagining and visualizing of what could be. The progress of this research is documented, along with the implications, hopes, and plans for its continued development. Although this article reports on the development of one particular tool, the author's intention is to inspire other art teachers to imagine, construct, and develop or build upon the lessons learned in this project. The hope is that in this process, art education will lead the way to implementing authentic embedded assessment processes across all education disciplines and grade levels.