This research aimed to understand how former prisoners make sense of their participation in carceral employment programs in terms of their reintegration into the labour market upon release. Following a social constructivist approach, semi-structured interviews were conducted with fourteen men living in Ottawa, Canada, who had participated in employment programs while incarcerated in Canadian federal prisons. Content analysis of the transcribed interviews showed that participation in work programs was perceived as beneficial for reintegration into the labour market if the individual received a provincially-recognized trade certificate, could count hours worked in prison towards an apprenticeship, or if engaged in a field of work that matched their aspirations in terms of future employment plans. Most participants noted additional advantages for engaging in work activities in prison, such as the use of work as a strategy to cope with feelings of idleness and estrangement from society while incarcerated. Participants who did not perceive participation as helpful mentioned that returning to the labour market was not desirable or was made difficult by plans to retire, to receive a government pension due to disabilities, mental health conditions experienced during and after prison, the stigma for being a former prisoner as overriding any potential benefit from the program, and parole conditions limiting or preventing the search for jobs in the community. Future studies investigating reintegration into the labour market upon release and seeking to understand how former prisoners make sense of their participation in carceral employment programs could focus on individuals who have completed their sentences and are not subjected to parole conditions. This would allow an investigation of the perceptions and experiences of those who are not impeded in seeking employment and have been actively searching for or engaging with employment upon release.