When scholars address the legitimacy question in authoritarian regimes this usually refers to the (quest for) regime legitimacy as such. However, non-democratic regimes are not static; they face specific legitimacy challenges at moments of major policy shifts as this means adopting positions the regime itself had declared illegitimate before. Drawing on empirical evidence from the current Cuban reform process, this paper seeks to analyze the interplay of domestic and international dimensions in the discursive, procedural and material mechanisms by which an authoritarian regime seeks legitimicy for reform from above.