Children with autism often experience substantial challenges in understanding, structuring, and predicting activities in their daily lives. Visual supports—the use of symbols to augment communication or to represent a series of activities or steps in a temporal order—have been successfully used by caregivers as an effective intervention technique to help children with autism to understand, structure, and predict activities in their daily lives. Often, however, these visual schedules are not interactive and interesting enough to draw and maintain attention; they can be out of date or inaccurate; they do not support communication and collaboration surrounding activities; and they are difficult to track for usage analysis. Thus, in this work, I developed and evaluated vSked, an interactive and collaborative assistive technology for students with autism, combining visual schedules, choice boards, and a token-based reward system into an integrated classroom system. I evaluated the system in three deployments over two years. The findings from these trials reveal practices surrounding the use of assistive technologies in classrooms and highlight important considerations for both the design and the evaluation of assistive technologies in the future, especially those destined for classroom use. While using vSked, the classroom staff reported improvements in the perceived quality and quantity of communication and social interactions in the classroom as well as reduced staff effort required to use visual supports.