Description: This paper explores the ambiguous feelings expressed by UK-based Gypsies towards literacy. Given the adaptations of Romani lifestyles resulting from changing socio-economic factors, to what extent is this reflected in attitudes towards education, and specifically, literacy? Traditional identity markers have become eroded in recent years in the UK (Fraser, 1995; Hawes and Perez, 1995). At the same time, in Roma communities across Europe, Gypsies continue to express a different group identity through performance (Guy y Blasco, 2000; Levinson, 2005; Levinson and Sparkes, 2005). In this context, the conflicts between contrasting banks of cultural capital, and the challenges confronting both Gypsy communities and the education system (suggested by Gheorghe, 1997; Liegeois, 1987; Liegeois, 1997), have become more acute. In the UK, barriers to engagement in the education system revolve around the compromises that become necessary (see e.g. Kiddle, 1999; Levinson and Sparkes, 2003; Levinson and Sparkes, 2004; Levinson and Sparkes, 2006). This paper investigates the traditional suspicion towards the written word, and considers the (often) paradoxical positions taken by individual Gypsies towards schooling, and more specifically, literacy. As literacy remains the currency of school-based learning, are attitudes towards it changing? If this is the case, what is the wider impact on Gypsy communities? And how do individual members of those communities negotiate the tensions between literacy-based learning and the traditional models of learning encountered in the home context? Methodology: The findings are based on an ethnographic study (1996-2000) carried out, primarily, in the South West of England. This study explored the interface between education, culture and identity among different Romani communities. This included semi-structured interviews with more than 100 individuals across the age range. The findings of that study are supported by a further (small-scale) study, currently taking place in the South West of England (2005-6), involving more in-depth interviews with a smaller group of participants, with a more specific focus on the impact of prolonged involvement in education and attitudes towards literacy-based learning. Conclusions: Individual Gypsies who remain within the education system when their peer group have left are often faced with uncomfortable choices. The implications go beyond the level of individuals; in a number of instances, not only do they find themselves becoming alienated from other family members, their own families become isolated from their surrounding communities. The challenge for themselves and the education system is to help foster a climate whereby the acquisition of the tools necessary for success in a literacy-based society does not entail the loss of a cultural identity founded, partially, on the rejection of literacy.