An autonomous task-prompting system is presented to increase workplace and life independence for people with cognitive impairments such as traumatic brain injury, intellectual disability, schizophrenia, and down syndrome. This paper describes an approach to providing distributed cognition support of work engagement for persons with cognitive disabilities. In the pilot study, a prototype was built and tested in a community-based rehabilitation program involving preservice food preparation training of eight participants with cognitive impairments. The results show improvement in helping with task engagement is statistically significant compared to the oral-instruction method. A follow-up comparative study with two participants evaluated the shadow-team approach against the proposed system. Although the number of participants was few, the participants were studied in depth and the findings were very promising. The results in the autonomous task prompting without staff intervention indicate that the performance is statistically as good as the shadow-team approach. Our findings suggest that acquisition of job skills may be facilitated by the proposed system in conjunction with operant conditioning strategies.