This paper seeks to contribute to the ongoing debate concerning effects of EU democratic and human rights conditionality in post-socialist environments that are least receptive to external democratisation efforts. More specifically, the paper scrutinises the process and outcomes of the EU sanctions enforcement against Uzbekistan between 2005 and 2009. Studies of EU political conditionality commonly draw on rational choice insights concerning the EU’s leverage vis-à-vis third states and regard lack thereof as the main determinant of the EU’s failure to achieve greater results in the countries without the EU membership perspective. This paper goes beyond these traditional explanations and argues that other factors must also be considered in explaining outcomes of EU conditionality. Particularly, the substance of EU demands and their implications for a target regime’s legitimacy and stability may account for the variance in the target government’s compliance with EU political conditions.