Professional learning is complex and is the result of a mix of experiences made in academic and workplace settings. An interesting step in the learning trajectories of professionals is represented by internship. Interns have to engage in boundary crossing when connecting academic learning with professional practices. An interesting issue to explore concerns the experiences of undergraduate interns when they encounter challenges in workplaces. Drawing upon Dewey’s notion of experience to examine internship learning, this article focuses on the role of sociomateriality when neophytes—interns—enter the workplace. Analysing semi-structured interviews with undergraduates (N = 38) performing their internship at the public relations and communication industry where internship is not an established practice, we present three findings. First, materiality of work activity plays a central role in organizing learning for interns at the workplace. Second, interns report networking at the workplace for convergence of work objectives which in turn provides opportunities and constraints for learning about the logic of workplace activities. Finally, interns report balancing between different identities during internship practice in order to direct their participatory efforts within the complex workplace organization. The value of internship learning calls for agency from the learners while considering the implications for the workplace organisations where learning experiences are located. Finally, we bring attention to the role of the workplace supervisors and faculty members in the development of professional learning in such complex professional learning settings.