From the second half of the nineteenth century, millions of Europeans migrated towards different parts of the American continent. Although it was, in many cases, fantasized in their minds, the migration to another continent represented, for these individuals and families, the opportunity to start a new story. The dream of a better life in São Paulo, for example, motivated the desire to leave the homeland. However, as constantly described by the historiography on the subject, the Europeans who arrived at the then promising coffee economy of São Paulo were soon faced with a reality of fragility in the face of certain structural conditions. Exploring situations that occurred mainly in the municipality of São Carlos, this chapter intends to analyze the situation of fragility faced by Europeans who went to São Paulo state, between the end of the nineteenth century and the beginning of the twentieth century. Contrary to what most immigrants imagined, the act of emigrating could expose the dangers and adversities that insertion in another society could cause. The objective, in turn, is to shed light on how fragility and contingency can be central elements in thinking about migratory trajectories.