This Canadian study investigated how the transfer of learning occurred in an employment preparation programme for adults with low literacy skills using a multi-site case study research design. Four different programmes involving trainees, instructors and workplace supervisors participated in the investigation. Results indicated that the transfer of learning occurs through various life roles that adults enact while participating in the programme; the Essential Skills of computer literacy, oral communication, and continuous learning are the guideposts for transfer and the time/role model of learning transfer helps explain the different instructional strategies used in the classroom and the workplace. The findings shed some light on how sociocultural learning develops in adult literacy groups destined for the workforce and the importance of the tri-partnership of the instructor, trainee and workplace supervisor.