The paper proposes a contextualized approach to local government transparency and its determinants. It starts by briefly discussing the distinction between local government compliance with transparency regulations and broader/more substantial local government transparency. A context-dependent measure of local government compliance with transparency regulation is built for the Romanian case and used to showcase significant variation from one local government to the next. Next, the paper approaches a set of inter-related questions concerning the predictors of compliance: Which previously identified predictors of compliance are also relevant in the Romanian context? Does external pressure exercised by the central government and/or civil society increase compliance with transparency provisions? In a strong leader local government system, how strong is the influence of the characteristics of the political leader in explaining compliance? The analysis finds that Romania has a distinct profile in terms of explanatory factors of local government compliance with transparency regulations. Characteristics of the local political and institutional environment such as the status, size, and financial autonomy of local governments are found to be relevant for understanding compliance in Romania. The paper also provides some points for practitioners.