Scholars have recently emphasized that a pro-democratic international order has affected patterns of regime change after the Cold War, but they have also noted that this order is presently weakening. In contrast, the international order in Interwar Europe has been highlighted as a good example of exactly the opposite – an environment that facilitates autocratic rule. But is it correct that the international order in Interwar Europe underwent a significant change in the direction of being an obstacle to democratic stability, and if so, why and when did this change take place? Our main goal in this paper is to present the conceptual and theoretical framework needed to carry out a comparative assessment of these issues. Based on recent works on the international dimension of regime change, we distinguish between two separate dimensions: the first concerns cross-national inspiration with regard to values (i.e., the Zeitgeist) and experiences, the second actual or perceived external pressure from great powers. Both dimensions influence the incentives and capabilities of domestic actors but they do so via very different mechanisms, which we spell out. On this basis, we attempt to identify the most important shifts within the international environment in Interwar Europe on both dimensions. Furthermore, to illustrate the mechanisms at play and to provide a tentative appraisal of the relationship between the international order and political regime developments, three cases – Czechoslovakia, Poland, and Spain – are analyzed. Finally, we briefly relate our findings to discussions about a current weakening of the pro-democratic international order.