The director of a university tutoring center collaborates with an Instructional Design and Technology professor and his students to develop an interactive multimedia format that presents at-risk college students with stories of people like them dealing with academic, financial, and personal issues. The scenario-based simulations (SBS) prompt students in a study skills course to openly, but safely, discuss the often sub-optimal decisions made by characters in the scenarios. This case takes readers inside the process of developing the SBS format from scratch. Transcribed interview comments from both the client (the tutoring center director) and the designer (the IDT professor) reveal an iterative and negotiated process rather than a systematic ADDIE process. The case highlights: 1) adapting corporate-style “soft skills” computer-based training (CBT) to higher education, 2) the role of CBT in a blended course, 3) rapid development of multimedia products, and 4) use testing of products with authentic learners.