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This paper examines a ‘good story’ of probation supervision, recalled 50 years later by Mary, who reported that her probation officer, Grace had ‘turned [her] life around’. Set within the context of more contemporary studies that focus on the ‘pains of probation’, of rehabilitation and of reentry, the chapter examines the context of Mary’s story, what was ‘good’ about it, and what ‘good’ was being done in telling it. The analysis focuses on how Mary and her probation officer secured her escape from the classed and gendered constraints, on the roles played by recognition and ritual in the process, and on how and why different aspects of Mary’s story were silenced and spoken, both at the time and in its telling to me. In conclusion, I argue that this ‘good story’ reveals how the complex and contingent relationships between social structures and human agency can be mediated and moderated by inter-personal encounters and relational dynamics (Weaver and McNeill, 2015); in Mary’s case -- and in her judgement – much for the better.