Students with mental retardation and deafness or deaf-blindness often need some type of communication system to communicate effectively with communication partners during community-based vocational training. However, students may need specific training to learn how to initiate requests for items or assistance, a skill identified as critical for job success. Students were taught to initiate requests using dual communication boards and gestures. Data were recorded on student performance using a multiple-baseline probe design in which data were collected during baseline, intervention, and generalization phases. Students were able to initiate requests with 80% to 100% accuracy with the communication system at vocational sites. Training students to initiate requests may need to be targeted when students are first learning a job, as this is when most naturally occurring opportunities exist.