Internationally, the issue of irregular immigration is highly contested and actors promote different frames in the news. In this article, we analyze the strategizing that goes on behind the scenes among nongovernmental organizations and public immigration authorities. Many studies have documented how strategic actors take advantage of mainstream news media conventions, but there is a dearth of research on how these frame sponsors critically reflect on their strategies. Based on ethnographic fieldwork and qualitative interviews, we analyze the dilemmas and challenges the actors face in adapting their communication strategies to the news media. The immigration authorities are systematic and professional in their media work, with easy access to leading media. Faced with the news media’s emphasis on dramatic individual stories, however, they struggle to find a media strategy that balances efficient communication with bureaucratic regulations and values. The NGOs, on the other hand, have the opportunity to exploit media conventions and pitch emotional, individual stories to journalists. Still, for both type of actors, the challenge is to expand the media interest beyond such stories to foster a systemic debate on immigration policy.