Educators of students with moderate and severe intellectual disabilities face a significant challenge in preparing their students while in school to function, acquire, and maintain skills that would facilitate successful performance in the workforce while in supported and/or independent employment after graduation. The field of special education still debates about the best way to teach students with moderate intellectual disabilities, the best setting for their instruction and the best instructional schedule. The current research investigated the effectiveness and efficiency of three instructional schedules in the skill acquisition and generalization of two-way radio usage to report task completion by high school students with moderate intellectual disabilities. The instructional schedules investigated were: (a) community-based instruction only (CBI), (b) community based instruction plus simulated instruction in the classroom-same day (CBISC) and (c) simulated instruction in the classroom only (SICO). A Multiple Probe Design across participants with intermittent probe trials within each instructional group, and an added generalization phase (Horner & Baer, 1978; Tawney & Gast, 1984; Alberto & Troutman, 2003) was employed in this study. Nine high school students with moderate intellectual disabilities, three in each instructional schedule, were taught to use a two-way radio to report task completion. The results of the study revealed that the CBI instructional schedule was the overall most efficient instructional schedule for skill acquisition. Two of the CBI participants required the least number of trials to learn to use a two-way radio to report task completion. The second most efficient schedule was the CBISC and the least efficient instructional schedule was the SICO. Based on Mean scores, learning efficiency appeared to be greater for the participants in the CBI and CBISC instructional schedule. These participants required the least number of intrusive prompts. Results indicated that the SICO instructional scheduled was more efficient for only one participant. This participant only required verbal prompts for acquisition of the skill. However, participant one on the SICO instructional schedule required the most intrusive prompts of all participants across groups. For generalization, the CBISC instructional schedule appeared to be the most effective. In this schedule, the two participants that concluded the study generalized the skill across three novel settings with 100% accuracy. The SICO schedule, also had two participants generalized the skill across three novel settings; however, one participant in that group failed to generalize the skill in two settings. The CBI instructional schedule appeared to be the least effective for skill generalization in this study. In this schedule, only one participant generalized the skill in all three novel settings.