Two recent developments – the WikiLeaks releases and the Arab Spring – have demonstrated the capacities of individuals and movements in advancing free expression, transparency and social change through the use of online and social media. However they have also highlighted new sets of challenges and threats that interfere with, and restrict, such media uses. In this article I will present an analytical framework for understanding and investigating these contemporary restrictions to freedom of expression, based on the dimensions of information control, access to infrastructure, critical resources and applications, surveillance, and physical repression. The model takes into account current trends such as the use of intermediaries in control regimes, and provides a global perspective that incorporates restrictions in both East and West. Further, I will outline how free expression advocates and civil society campaigns, such as the Icelandic Modern Media Initiative (IMMI), have contested these practices, and discuss whether their agendas confirm the issue areas highlighted above. The restrictions to, and the advocacy for, free online communication demonstrate some of the key struggles and contestations on freedom of expression in the current digital media environment, the strategic points of intervention by different actors (states, businesses, and civil society), and the requirements for “modern freedom of expression”.