This chapter aims to understand the options for distributing newspaper content online and offline. By adopting a case study approach, it analyses the content strategy of one of the most widely read newspapers in Portugal, Jornal de Notícias (JN). Several data sources were used, including an interview with the director and a survey with 570 readers. JN shared a much larger number of news in the paper version. It is a newspaper focused on difficult news; however, it combines this strategy with the use of infotainment, especially in the online version. This chapter highlights the importance of aligning the content strategy and the preferences of readers.