In recent decades, a good part of the literature on civil disobedience has challenged John Rawls’s classic liberal model of civil disobedience by normalizing disobedience as part of democratic politics. It has little to say, however, on how courts should deal with normalized disobedience. I showcase how Taiwan’s courts have dealt with disobedience since 2008, a time when social and political movements began to be energized by a government seeking closer ties with China. I analyzed how the courts negotiated legality, social legitimacy, and political divide. I identify five models of judicial responses, which include “static formal law”, “conflict management”, “tolerance”, “dynamic formal law”, and “adjudicating change”. I argue that step by step, Taiwan’s courts were driven to adjust and relax legality in order to accommodate disobedience, and yet such tampering with legality poses risks to the institutional legitimacy of the judiciary and further aggravates political polarization.