Stroke is the fourth leading cause of death and the major cause of disability in Singapore. The number of stroke survivors is expected to rise with the increase in the ageing population. This paper describes how occupational therapists are involved in stroke and work rehabilitation in Singapore. A retrospective study of stroke clients referred to a vocational assessment unit in 2004 showed that 55% of the clients were able to return to work. The majority of the clients changed their job positions from blue-collar workers to clerical workers. On the other hand, the main reasons for poor outcome were: unfit to work in general, needed further rehabilitation, further medical care was indicated, failed to meet appointments and withdrawal from the job trial. Three case vignettes are discussed to illustrate the multifactorial aspects influencing positive work outcomes. Further research is needed in exploring the factors that affect stroke rehabilitation and return-to-work outcomes.