Given a substantially more volatile, less predictable global business landscape, export-oriented small and medium-sized enterprises (SMEs) are facing intensive pressure to reassess their strategies. In this light, this dissertation consists of four empirical studies exploring SMEs’ export behavior across institutional environments. The first contribution analyzes the pertinence of SMEs’ innovative capacities for their exports. Based on a systematic quantitative integration of around forty years of literature, it uncovers export-enhancing effects of innovation, while also revealing how theoretically deduced institutional moderators matter. The second study examines the nexus of intangible assets and SMEs’ export behavior. Building on a theory-driven, comprehensive model, the meta-analytical findings inter alia show differential effects of human and relational capital, contingent on the stage of export involvement. The third contribution focuses on the role of financial institutions. By combining distinctive streams of literature and drawing on a panel of German SMEs, the analyzes underline the pertinence of bank-based financing schemes in explaining export patterns. Importantly, the results indicate that effects are context-dependent. The fourth paper explores the association of distinctive macroeconomic as well as institutional factors and the share of SMEs in a nation’s exports. Amongst others, the findings suggest that trade openness gains in relevance when more distant markets are targeted. Moreover, the importance of appropriate practices to account for geopolitical risks is emphasized. Consequently, this cumulative dissertation contributes to a more nuanced understanding of the mechanisms underlying different dimensions of SMEs’ export behavior, while adding to the academic discourse and providing valuable practical insights.