This article explores how being a small island jurisdiction affects actors in the journalism sector. The media is often referred to as the fourth estate, an institution inherently important for democracy. By scrutinizing politicians, journalists have the possibility to reveal transgressions and provide the public insight into how powerholders are performing as state officials. With this knowledge, the public can make informed decisions as to who will earn their vote in coming elections. This article studies the space for manoeuvre of investigative journalism in a small island state where the interconnectedness of people – journalists, sources, and powerholders – is a fact. It does so by studying the case of Cape Verde, a small island nation with 560 000 residents. Interviews with 12 Cape Verdian journalists from a range of the most important media outlets in the country, reveal that although freedom of expression and freedom of the press are constitutionally guaranteed, there are substantial practical limitations of free journalism. Respondents tell of widespread self-censorship, underfunding, and political interference as aspects that limit the possibility of conducting their work in a manner that would make them the watchdog institution that most of them aspire to and wish they could be.