The growing potential of Tangible User Interfaces (TUIs) for education in the child-computer interaction community has yet to explore how TUIs can best be designed and evaluated for complicated and dynamic classroom settings. This thesis aims to help researchers and designers gain a better understanding of what matters when embedding TUIs within a classroom environment by exploring themes of contextual concerns derived from teacher interviews. Through a comparative exploration, comprised of two studies, I examined both predictions of use and actual classroom integration in an effort to understand important design and evaluation considerations. I present results that are a culmination of data from both studies to form a more full picture of the problem space. I contribute both analytic themes and design considerations for TUI tabletops for primary educational classrooms. I introduce The Activity Checklist as a tool to guide existing qualitative inquiry methods for 'real world' deployments.