This paper reports on the findings of two qualitative exploratory studies that sought to investigate design features of help options in computer-based L2 listening materials. Informed by principles of participatory design, language learners, software designers, language teachers, and a computer programmer worked collaboratively in a series of design sessions. The participants first evaluated researcher-generated prototypes, designed prototypes for two language proficiencies (beginner and upper intermediate) and iterated designs on both paper and screen. Analysis of the reworked prototypes resulted in five features of help option design: type, location, sequence, click-through, and display. Analyses of the interaction data showed that consensually the participants favored help options that are easy to use, promote learner control, support guidance, and stimulate learning.