This paper is an exploratory study to understand the content marketing practices in Estonia, a current trend that ties together journalism, communications, and advertising. Estonia is a small market where the ‘guilds’ of journalists and PR professionals are rather intertwined. Trends occurring here may provide suggestions for larger markets and future developments. A qualitative study was conducted in Spring 2018. The objective of the study was to describe the problems and potential complications arising from the reorganization of traditional areas of activity of agents operating in the field of the communications industry – specifically in the context of content marketing, and from the viewpoint of representatives of PR agencies. The article begins with putting the phenomenon of content marketing into a wider societal context – and specifically that of the Estonian media ecosystem. The possible influences of content marketing on such important realms, and such defining factors as trust (Luhmann 2000), social capital (Bourdieu 1995) the integrity, independence, and the interactions between the different fields (ibid) are discussed. The results of the survey indicate that the field of public relations is changing as a result of the forces from the other neighbouring fields, that of journalism and advertising. The paper points out that the issue of trust and trustworthiness and the origins of ‘the media’ need to be addressed in order to provide integrity and transparency.