This design case examines what program leaders learned from failures in the design of a program of authentic learning about teaching diverse audiences through educational outreach. The program was initiated and then redesigned to develop the teaching and communication skills of graduate students from a wide range of backgrounds by engaging them in authentic experiences with middle school teachers and students. Analysis of post-program data revealed seven design failures related to the lack of upfront analysis to inform the program design. Each design failure was detailed through a fishbone diagram method to identify the corresponding contributing factors. The failures in this design case reinforce the need for upfront learner analysis and contextual analysis. A participatory design was also suggested from the post-program data analysis. An instructional design model was recommended for continuous program redesign.