This Brief introduces a novel research approach to investigate freedom of the press in Hong Kong. The authors pair computational analyses from the field of natural language processing with qualitative content analysis of patterns of journalistic practice in volatile political settings. Together, these shed light on the evolution of press freedom in Hong Kong since its return to Chinese sovereignty. Providing an interdisciplinary perspective, the Brief will appeal to a wide range of readers with interests in computational social science, public policy, political sciences as well as policy-makers, think tanks, and practitioners who focus on the China-Hong Kong nexus.