Private tutoring is not a new practice in Italy, having accompanied the structuring of the education system since the middle of the 19th century. It has, however, assumed different guises over the years, depending on the political spirit of the age, and whether Italy was under the sway of liberalism, fascism or post-war democracy. The growth in private tutoring since the turn of the century has different causes, among which are a number of reforms introduced by the two right wing governments that led Italy between 2001 and 2011. This chapter provides a historical and critical overview of the diverse root causes of private tutoring, as well as its significance to different groups of citizens. It thus illustrates the fluid versatility and context-dependent features of the phenomenon. The chapter further suggests that under certain political configurations of hegemonic power, private tutoring can operate as an enclave of resistance, offering some forms of economic and socio-cultural redress for a persecuted class of individuals or groups. As such, private tutoring operates as much in relation to the political as it does in relation to the economic, and expresses the embedded tensions, struggles, and aspirations associated with conflicts over the aims of education.