The year 2022 marks the fiftieth anniversary of Okinawa's reversion to Japan. This article examines the Japan Civil Liberties Union's 1955 solidarity activism on occupied Okinawa, which generated Japanese civil society's first awakening to the “Okinawa problem.” The Asahi Shinbun's front-page article on the organization's publication “Human Rights Problems in Okinawa” and its follow-up coverage triggered public debate influencing Japan/U.S. official policies on Okinawa. Drawing on archival evidence, the article illuminates the contested nature of Japanese activism caught between Cold War Asia and decolonizing Asia. It argues that the 1955 activist movement shaped the subsequent trajectory of Japanese engagement with the “Okinawa problem.”