The current study investigated whether four Deaf students with developmental disabilities could learn a chain of independent living skills and follow activity schedules using a combination of the two iPod Touch applications (apps): inPromptu and First Then Visual Schedule. Using a multiple probe across participants design, the study examined the effects of the intervention on skill acquisition and generalization to untrained independent living skills and novel sequences of activity schedules after the students mastered the use of the two iPod apps. Least-to-most prompting was used to teach the two iPod apps. The results showed all participants successfully acquired a variety of independent living skills using video prompting. Three of the four participants were able to follow varied and novel activity schedules after they were trained to follow the fixed order activity schedule. Multiple exemplars were needed for one participant to master varied and novel activity schedules. In addition, all participants successfully followed activity schedules in an untrained setting (e.g., school dorm). This study extended the current literature on video prompting and activity schedules by incorporating both approaches and testing their generalization effects. As such, the study provided new practices that may increase functional independence for Deaf students with developmental disabilities.