This paper details a framework for evaluating the potential of particular forms of technology for supporting student engagement with mathematics. I propose that, focusing on the strength of affordances to engage in particular ways allows us to begin to build an analytic frame that serves two purposes: (1) to begin to document learning as an interaction with larger bodies of data; and (2) to make and evaluate conjectures about the potential of different technologies for supporting high quality engagement with mathematics. I describe design iterations from previous work that leveraged this framework as an example of how this framework could be used and why it has proven to be valuable. [For the complete proceedings, see ED584443.]