Vocational and career wellbeing is of essential importance for the successful reintegration of ex-offenders back into civil society, becoming healthy and productive citizens who contribute to the common good of the general society in which they live. Within a Canadian context, this article intends to draw attention to the vocational wellbeing of adult ex-offenders who have served time in prison after a conviction. To this end, the article identifies the major career issues for ex-offenders, and then links theoretical knowledge and research evidence to career development interventions to counter career problems experienced by this population. It sheds light on the pertinence of utilizing career theories to inform and direct career counselling interventions that can improve and enhance the career wellness of this population.