Abstract: This thesis casts new light on the immigrant experience, focusing on one extended Scottish Jewish family, the descendents of Rabbi Zvi David Hoppenstein and his wife Sophia, who arrived in Scotland in the early 1880s. Going further than other studies by exploring connections and difference through five generations and across five branches of the family, it uses grounded theory and a feminist perspective and draws on secondary sources like census data and contemporary newspaper reports with the early immigrant generations, oral testimony with the third and fourth generations and an innovative use of social networking platforms to engage with the younger generation. It explores Bourdieu’s theories relating to cultural and economic capital and the main themes are examined through the triple lens of generational change, gender and class. The thesis draws out links between food and memory and examines outmarriage and ‘return inmarriage’. It explores the fact that antisemitic and negative reactions from the host community, changing in nature through the generations but always present, have had an effect on people’s sense of their Jewish identity just as much as has the transmission of Jewish identity at home, in the synagogue, in Hebrew classes and in Jewish political, educational, leisure and welfare organisations. It makes an important link between gendered educational opportunities and consequent gendered intergenerational class shift, challenges other studies which view Jewish identity as static and illustrates how the boundary between ‘insider’ and ‘outsider’ is blurred: the Hoppenstein family offers us a context where we can see clearly how insider and outsider status can be self-assigned, ascribed by others, or mediated by internal gatekeepers.