We propose a three-part framework describing support tools for users of complex software applications such as enterprise resource planning and decision support systems. The model is motivated by the objectives of learning, performance, and analysis and is grounded in the theories of constructivism, pragmatism, and reflection respectively. This mapping is supported both by results of prior research and by a case study formative evaluation of a complex, cognitive support system developed for antiterrorism resource allocation. The work contributes to the field of system usability by providing an integrative framework linking established theoretical positions with empirical research on human-computer interaction.