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Working with the family members of ex-offenders is a daunting and newly developing aspect of offender rehabilitation in Singapore.  A small scale practice research project was carried out by three social work practitioners and two academics over a period of 22 months, with the aim to explore the pertinent issues and challenges in working with family members of ex-offenders.  Systematic documentation of the process of working with three cases was carried out.  Specific skills and strategies were suggested, and recommendations for changes to service delivery and policy for working with ex-offenders and family members were made to the authorities.  This article highlights the enriching journey of collaboration between the academics and practitioners.