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Small and medium-sized enterprises (SMEs) are increasingly important actors of the global market and are particularly exposed to be affected in a scenario marked by an ongoing process of deglobalization and impacts of the COVID-19 pandemic. Both of these phenomena potentialize the liabilities that firms experience abroad, namely foreignness and outsidership. Despite extant progress in understanding the challenging aspects of operating in international markets, there is not much knowledge about how firms’ decision logic frames their international behavior as these firms interact with the various liabilities of firm internationalization. In the same spirit of research that have leveraged the study of SMEs’ international trajectories to unveil new aspects of firm internationalization as a phenomenon, the general purpose of this thesis is: To explore what lessons from SME foreign market expansion can help to understand internationalization decision-making under challenging circumstances. Such a purpose makes room for research questions that call for the use of microdata to solve problems with broad implications for a population of firms. Empirically, this thesis builds on a quantitative research design based on survey data collected from 885 SMEs distributed in Brazil, China, Italy, Poland, and Sweden. Analyses of these data were performed with multiple regression equations, structural equation modelling using partial least squares, and multinomial logistic regression. Results help to understand how the liabilities of foreignness and outsidership can be associated with uncertainties that, together with the resources available to be used by the firms, can lead SMEs to adopt non-predictive strategies to operate abroad. In addition to that, they also indicate how elements of those liabilities can be perceived in dynamics that moderate outcomes of the strategies selected by the SMEs. Such findings provide a platform to extrapolate insights and propositions to advance the discussion of internationalization decision-making under modern challenges such as deglobalization and the COVID-19 pandemic. Theoretical implications of this thesis hold potential to touch the more general research on firm internationalization, whereas its practical implications may help in evolving the support tools available for assisting internationalization decision-making.