This article documents the historical and semiotic factors that have entailed a normative ambiguity of “the internship,” both as an ideological sign and as a participant role that has increasingly mediated the relationships between higher education and careers in the United States. We present comparative life history narratives of two interns drawn from a longitudinal interview study, which illustrate the negotiations, experiences, and consequences that the ambiguity of the internship participant role entails for students attempting to navigate the transition between education and employment. We argue that the stable semiotic ambiguity of the internship participant role is a consequence of a political economy of collusion, in which employers, educators, and students benefit from the emergence and spread of the internship economy, with students finding it uniquely useful to establish credibility in the highly competitive employment market. We point out how students’ class-based resources, networks, and positionalities constrain the possible outcomes for them from this process.