In this paper, we discuss the challenges involved in developing an infrastructure to support a new generation of analytic tools for information analysts. The infrastructure provides data for establishing context about what the analyst is doing with the analytic tools, supports an integration environment to allow suites of tools to work together, and supports evaluation of the analytic tools. We discuss the functionality of the Glass Box, the challenges of evaluating adaptive systems including the capture of data for evaluation metrics, and lessons learned from our experiences to date.