Native advertising is often perceived as the future of both media and advertising. Notonly is it said to lead to better, more effective advertising, it is also thought to be partof the solution to journalism’s current economic crisis. Both supporters and critics areconvinced of its future success: the transition to native is supposedly both smooth andunproblematic. This chapter seeks to nuance such accounts, using the example of Sweden.There are at least three main dilemmas, or barriers – economic, ideological/organisationaland regulatory – for those who wish to ‘go native’ or in other ways maximise theinfluence of advertising upon editorial content. Analysing them suggests some avenuesfor action, including targeted protection of particular forms of media content such asnews, and greater public support for a structurally divided media system: if commercialmedia can no longer manage to uphold a ‘wall’ within their companies, then the ‘wall’might instead run through the media system at large.