Montenegro has been praised for advancing the farthest in the EU accession process. Each EU candidate state must align its legal, political, and economic framework with the acquis. The negotiation process has lasted for ten years, and although much has been achieved in harmonizing the legislation, progress reports warn that implementation needs to be improved. The core of the rule of law is effective judicial protection. Montenegro adopted the necessary amendments to its Constitution in 2013 and carried out justice reform as expected by its Western partners; however, the rule of law backsliding has become evident. This chapter analyzes the transition process and its effects on the rule of law. It identifies the extrinsic and intrinsic layers of reform that correlate with the ongoing institutional and constitutional crises. In this framework, the chapter shows the vulnerability of the legal system against political constraints such as ethnopolitical division, partocracy, hegemony, and “stabilitocracy.” The Constitutional Court was held hostage by opposing political blocks failing to elect judges. The chapter suggests that Montenegro is officially in the fourth transition period, potentially presenting an opportunity for a radical turn in political culture amidst the rising populism and contested geopolitical issues. The country needs to be freed from hegemonic tendencies in governance with a new constitutional framework that would secure respect for the rule of law.