Many people living with HIV/AIDS (PHAs) have experienced significant improvements in their health over the last few years, to the point that many are considering returning to work. The objectives of this study were to develop a model of return to work which could apply to chronic illnesses with a fluctuating or uncertain course. Issues related to health, work and return to work were explored using in-depth interviews with 20 PHAs in Toronto, Canada, who had been on long-term disability for at least five years. Data were analyzed using a grounded theory approach. Contextual factors like the approach of disability and health (drug) insurance plans and intervening conditions like PHAs' current activities influenced their consideration of returning to work and the strategies they employed as a result of considering such a return. More than two-thirds of the sample had undertaken more activities as their health improved. The three study participants who had returned to work either had an opportunity for a low-risk trial of work or could return to their old job. Employers and disability compensation plan administrators, assisted by AIDS service organizations and governments, can facilitate return to work for PHAs by reducing the risks of and removing the barriers to returning to work.