Open and free internet-based platforms are seen as an enabler of global free expression, releasing writers from commercial and space constraints. However, many are working without the assistance of an in-house lawyer, or other legal resources. This may lead to undue suppression of public interest material, with important implications for freedom of expression and the democratic function of media. Two online surveys among digital and online journalists in England and Wales in 2013 indicated that the majority of encounters with defamation and privacy law take place outside the courts, with few formally recorded legal actions. This was particularly evident in a sample of 'hyperlocal' and local community publishers. In light of the results, this paper calls for a reappraisal of overly simplistic judicial and media applications of the 'chilling effect' doctrine, in order to expose its subjectivities and complexities. Additionally, attention needs to be paid to global and cross-jurisdictional media-legal environments, in order to help develop better internet policy and legal frameworks for protecting legitimate expression.