The World Wide Web facilitates user access to knowledge-based decision support systems. Such web-enabled systems can provide users with advice about how decision-makers exercise discretion. GetAid, developed using the web-based shell environment WebShell, is an example of a web-based decision support system operating in a discretionary legal domain. This paper presents the Context, Criteria, Contingency evaluation framework for knowledge- based systems, general in design but geared towards the evaluation of legal knowledge-based systems. Central to this framework is a hierarchical model of evaluation criteria arranged in four quadrants: verification and validation, user credibility, technical infrastructure and the impact of the system upon its environment. This framework frames an evaluation both in terms of the context of use of the system and the context of its evaluation and includes guidelines for the selection of appropriate evaluation criteria under differing contingencies. A case study is presented describing the use of this evaluation framework in planning the evaluation of the web-deployed GetAid system.