The article analyses how specific market and political conditions restrain the technology-driven change of the news industry and affect the way the new media landscape is taking shape in Italy. The interviews and secondary data analysis show that the digital transition (the growth of online news and the move to digital terrestrial television) has only limited implications for the pluralism of information within the Italian media system. The TV sector is still dominated by a few legacy broadcasters, and the structure of the online news market substantially reflects that of the newspaper sector. Although the new media, compared to the traditional media, have lower technological barriers inhibiting entry, market and political factors still hinder the entrance of newcomers. A major role is played by the dominant positions of two broadcasters (Rai and Mediaset) in the Italian media sector, the lack of effective media policies and the Berlusconi’s conflict of interest. Finally, the digital transition is more significantly impacting the power relations between broadcasters and newspaper organisations in the online news market, which is dominated by established press publishers who, because of the crisis in their traditional sector, have strongly invested in their online activities.