There have been significant alterations in the EU enlargement policy when it comes to the western Balkan countries mainly related to the scope of the criteria and approaches towards application of the conditionality policy. The paper aims to illuminate EU political conditionality’s application in the accession processes of the western Balkan countries, concentrating on the conditionality instrument of benchmarking and monitoring. It examines whether the EU political conditionality is the driver enabling the western Balkan countries to advance in the accession process, and looks for patterns of consistency in the application of political criteria and related conditionality in the judiciary and fundamental rights policies. The methodology utilizes a comparative case study approach, identifying innovations and principles governing the negotiation process of Croatia and Montenegro, the application of political conditionality related to the judiciary and fundamental rights policies, and actions taken by these countries in order to meet the political criteria. In addition, it makes an analogy to the case of Macedonia, which has not yet started accession negotiations, drawing parallels and examining the comparable instruments and approaches which in major part concern the rule of law area.