Street papers are publications produced specifically for sale by the homeless and other vulnerable people in many countries around the world. Their social status is, however, often conspicuously unstable: 'Get a job!' has been reported as a common insult addressed to vendors, and street paper organisations have responded with their own rhetoric and strategies that aim at disrupting any analogy with begging. The present analysis frames these rhetorical confrontations as a struggle over economic legitimacy, highlighting some of the ways in which social actors build and sever the normatively loaded associations that position them and others in social space, and how the 'experimental' combination of business and social responsibilities tests social actors' abilities to adapt to this practice.