Evaluation of the design and implementation of a web-based e-health application offers an opportunity to apply extensive research findings and evidence-based practices from the learning and performance literature. In this study, we examined how interactions between stakeholders influenced the design, implementation, and outcomes of an e-health education system. The online system was designed for adults with diabetes. A midsized suburban medical practice in the Midwest partnered with a private sector information technology provider and a university research team to develop the system for patients. Design of the support system was based on a model developed by Schaffer and colleagues, and the implementation strategy was informed by Ely's conditions-of-change model. Analyses of design and pilot study implementation processes were accomplished through the lens of responsive evaluation. Discussion of the successes, tensions, and challenges related to the design of learning and performance environments in the e-health context will guide future system design and evaluation efforts.