This thesis critically re-examines the “Norfolk Island Legend” by tracing the lives of 361 men returned to mainland New South Wales during 1839, under the Remissions Act. Employing archival sources, including convict records, petitions, and correspondence, and newspapers, it presents a collective biography that challenges the portrayal of Norfolk Island prisoners as uniformly brutalised and incorrigible. The study merges quantitative analysis with qualitative life histories, revealing the varied pre- and post-island experiences of these men. By foregrounding the human detail within larger penal narratives, this research both questions the validity of the Norfolk Island Legend and contributes to a deeper understanding of punishment and reintegration in convict New South Wales.