Knowledge of the convict period in New South Wales has been substantially expanded and enriched through a number of revisionist scholarly studies in the last quarter of the twentieth century. The cumulative result has been the establishment of a number of new orthodoxies. These studies have drawn on a number of analytic frameworks including feminism and cliometrics, successfully challenging the previous historiography. The rich archival sources in New South Wales have been utilised to reformulate the convict period by a number of scholars, demonstrating the complexity of life in the penal colony. Academic divisions between what are regarded as “Australian” history and “British” history have imposed their own agendas on writing about transportation. This study challenges this imposition through an examination of petitioners’ approaches to the home and colonial administrations. A lacuna in the scholarly studies has been a lack of attention to transportation’s consequences for married couples and their children. This study seeks to narrow that gap through these petitions. The findings of the study demonstrate the continuation of links between those who were transported and those who remained in Britain. It is argued that these findings have important implications for future research within Britain, and that what is disclosed by these petitions and the individuals who were involved in on-going communications cannot be restricted either to Australian or convict histories. Our knowledge of what transportation meant to individuals in the periphery as well as those in the metropole is diminished if the focus remains firmly on the settler community. Supplementary material from contemporary sources as well as the official records passing between the two administrations has been utilised and these supplementary sources suggest that there was a broad division between official publicly stated policy and practice in respect of transportees’ family circumstances. Chapter One establishes the architecture of the thesis and explains the methodology adopted. Chapter Two offers a reinterpretation of the colony’s formation in 1788 and inserts the “convict audience” of that day into the historiography . Chapter Three examines two petitioners writing from different gaols in Britain prior to their expected transportation. A resolution of the division between cliometrics and this more qualitative humanist approach is proposed. Chapter Four is a study of petitioners in Britain and a study of the process required for a reunion and reconstitution of family units in New South Wales. Chapter Five seeks to a resiting of male convicts as family members through an examination of a number of contemporary sources. Chapter Six examines the petitions raised by husbands and fathers for their wives and families to be given free passages to the colony. Chapter Seven provides case studies of three transportees and their experiences of the petitioning process. In Chapter Eight the focus broadens out from married men to examine and provide a revision of convicts’ correspondence with their relatives and friends in Britain. Such correspondence has previously provided the basis for nationalist interpretations; the revision here suggests that such interpretations are anachronistic. Chapter Nine is an extended metaphor drawing the material together to the conclusions of the study.