In the present study, we examine the manner in which firms’ experiential learning in challenging institutional environments shapes their entry strategies in subsequent international acquisitions targeting comparable contexts. Specifically, our research delineates the nexus between the institutional expertise firms garner from operations in countries characterized by deficient institutional frameworks and the level of ownership they subsequently elect in acquisitions within similarly constituted environments. Utilizing a dataset comprised of 3,577 cross-border acquisitions aimed at emerging markets, spanning the period from 2010 to 2019, we find that institutional experience serves as a moderating variable. This moderation influences the impact of corruption, economic freedom, and political stability on the proportion of ownership stakes acquired during the transaction. While firms are generally inclined to augment their ownership levels in acquisitions where the institutional environment is more favorable, our findings paradoxically reveal that institutional experience amplifies, rather than mitigates, the relationship between extant institutional conditions and the chosen level of ownership, contrary to our initial hypotheses. © The authors.