The arrival of the Internet and the financial crisis of 2008 fundamentally disturbed the media industry. Nowadays, journalism is still in the middle of a crisis, as media outlets have not managed to find a universal and functional business model. Independent media from Moldova experience most of the industry’s troubles. Furthermore, they are forced to operate in a restrictive environment, where they may suffer from political pressure or unfair competition. The present paper aims to study how this environment influences the sustainability of independent media outlets and how these institutions cope with the restrictive conditions. Moreover, the study touches upon the revenue models of the media organizations and their future plans of development. Within this study, three independent online media from Moldova have been analyzed. The research has been carried out using case study methodology and the data have been collected by conducting qualitative interviews with editors-in-chief and managers of the media outlets. The major theoretical framework of the study is the Industrial Organization Theory and its underlying Structure-Conduct-Performance (SCP) paradigm. According to the theory, the performance of an institution depends on the environment in which it competes. After six in-depth interviews had been conducted, the thematic analysis of their content revealed the following findings. The analyzed outlets rely exclusively on advertising and foreign aid and have failed yet to develop other sources of income. The sustainability of an independent media outlet is influenced by the advertising market, the politics and other media outlets. In order to cope with the restrictive environment, the media institutions adhere to their editorial policy and journalistic values. Additionally, the study confirmed the validity of Industrial Organization Theory and adapted the SCP paradigm to Moldovan media industry.