As a subset of the Information systems (IS) discipline, Decision Support Systems (DSS) development research needs a broader conceptual lens in order to evaluate design qualities specific to DSS. This paper presents a development-oriented approach for evaluating DSS applications. Based on a design science mental model proposed by Peffers, Tuunanen, Rothenberger and Chatterjeea (2008), our study outlines a new application area of this conceptual approach through a case demonstration of DSS development through various design checkpoints. To assess the proposed developmentoriented evaluation strategy the paper also describes a qualitative investigation that has been undertaken to assess the conceptual approach with target industry DSS users and developers. The findings suggest that this strategy is of use for improving the overall design qualities in every phase of DSS development, and could be useful for evaluating DSS design with target users and DSS designers within a socio-technical design context.