This study investigates the pursuit of international entrepreneurial opportunities (IEO), challenging the traditionally linear perception of this process. By utilizing the abductive process research approach and a critical realist lens, we evaluate IEOs within various contexts over time aiming for both iterative and flexible theorizing. The research explores the reciprocal interaction between entrepreneurs and their environments, examining how contexts shape opportunity pursuit and its evaluation, which affect favourable business strategies. In turn, opportunity pursuit influences the way entrepreneurs perceive surrounding environments and act upon that perception. Our findings reveal that opportunity pursuit is a non-linear process which is deeply influenced by integration with context. We highlight three main contributions to opportunity theory: the multiplicity of contexts and their effects, path dependence, and the reconsideration of temporality in opportunity pursuit. The study advocates for a paradigm shift towards recognizing the complex, non-linear nature of entrepreneurial opportunity evaluation, moving away from oversimplified traditional models. Our research advances the IEO discourse by identifying inefficiencies in current debates and suggesting pathways for further investigation.