The chapter analyses migrant men, masculinities, and remittances in the context of South Indian mobility to Italy, drawing from long-term multi-sited research in Rome and Kochi. The relational and processual analysis considers how engagement with remittances changes according to the migration ends, life-cycle stage, and actor. The notion of double discredit captures the unorthodox positioning of lower-class migrant men with respect to social scripts that emphasise their hegemonic role as leading remitting subjects. Double discredit is generated by the inversion of male-centred migration pathways—deemed by the upper middle class to contaminate the masculinised history of Kerala’s transnationalism, social progress, and cosmopolitan success. Further, double discredit results from the racialisation of subaltern migrant men as feminised subjects who are simultaneously trapped between downgraded work and dependency on women.