Despite an increased interest in the phenomenon of stigma in organizations, we know very little about the interactions between those who are stigmatized and those who stigmatize them. Integrating both the perceptions of the stigmatized worker and the stigmatizing customer into one model, the present study addresses this gap. It examines the role of stereotypes held by customers of stigmatized organizations and metastereotypes held by the stigmatized workers themselves (i.e., their shared beliefs of the stereotypes customers associate with them) in frontline exchanges. To do so, data regarding frontline workers (vendors) of homeless-advocate newspapers from 3 different sources (vendors, customers, trained observers) were gathered. Multilevel path-analytic hypotheses tests reveal (a) how frontline workers’ prototypicality for a stigmatized organization renders salient a stigma within frontline interactions and (b) how stereotypes by customers and metastereotypes by frontline workers interact with each other in such contacts. The results support a hypothesized interaction between frontline workers’ metastereotypes and customers’ stereotypes—what we call the “stigma magnification effect”. The study also derives important practical implications by linking stigma to frontline workers’ discretionary financial gains. (PsycINFO Database Record (c) 2015 APA, all rights reserved)