Drawing on the theory of the legal opportunity structure, this article traces the progress of prison reform in Taiwan by highlighting how a case of parole revocation in the beginning led to an overhaul of the prison system in the end. This article argues that, through four interpretations of the Constitutional Court and the legal opportunity structure shaped thereby, including the split between courts, creation and expansion of inmates’ access to court, and the support from allies, the prison reform was eventually achieved. Theoretically, this article makes two contributions to the literature: (1) the combination of inactive legislature and reactive executive branch as the political context is decisive to the openness of the legal opportunity structure for it increases the receptivity of a proactive judiciary; (2) the international human rights frame incorporated into the legal stock by the Constitutional Court made the prison reform an ongoing process rather than a done work.