As the opportunities for online political expression grow exponentially, aggregate levels of e-expression vary strongly across countries worldwide. The paper explores contextual factors enabling or restraining e-expression, particularly media dependence, democratic experience and civil society robustness and combines them with micro-level demographics, capacities, and motivations. Based on multilevel logistic modelling of 2014 ISSP 'Citizenship II' data [ISSP Research Group. 2016. "International Social Survey Programme: Citizenship II - ISSP 2014 (Version 2.0.0) [Data file]." GESIS Data Archive.], it shows that e-expression is not dependent on a robust civil society, but on the years spent under democratic rule and the level of media dependence. The latter mediates the predictive effect of political trust, which is negative but ceases in countries with dependent and unfree media. The findings challenge assumptions on the mobilizing potential of digital tools in less free countries, particularly for critical citizens who wish to express grievances outside the circuit of official but closed or monitored channels. In contrast, a reinforcement effect is not only found on the individual-level but also in terms of a democratic digital divide between free and consolidated as well as dependent and young/no democratic regimes. Thereby, the paper contributes to our theoretical understanding of the institutional factors shaping e-expression