The authors conducted a secondary deductive analysis of 53 written reflections submitted by 12 middle-level mathematics preservice teachers (PSTs) who had each participated in up to five web-based interactive scenarios. The reflections were originally designed to gather data for a previous study about the development of professional judgement using web-based interactive scenarios. However, in reviewing the reflection documents, the authors concluded that there was sufficient data to support a secondary analysis that might inform future scenario development. The article describes the design framework and original development of the scenarios, written by a panel of retired public school administrators and university teacher education faculty members. In anticipation of continued and future development of additional scenarios, several technology delivery formats were used, including still photos with text-based dialogue, video clips with human actors, computer animated images with computer synthesized speech, and computer animated images with human speech dubbed in for audio. The analysis revealed five of nine design elements: commentary, artifacts, personal choices, technology-general, and products were mentioned most frequently by PSTs. The remaining four design elements: technology-positive, branching, control, and technology-negative, provided nuance to the recommendations for future web-based interactive scenario development.