This chapter investigates the media context of Myanmar’s recent political reforms and transition of power. Drawing on interviews with more than 50 Yangon-based journalists, editors and media trainers, this chapter analyzes the obstacles to achieving greater media freedom in Myanmar. The nation’s difficult transition is examined in the context of similar challenges facing media systems in democratizing states throughout Southeast Asia and beyond. In particular, press ownership structures, political polarization, a passive civil society and the prevalence of social media as an information source are identified as key factors blighting free speech and a free media in Myanmar and across the region.