This dissertation investigates the persistence of strategic sophistication across different scenarios. In daily life, people often make decisions based on their beliefs about other people’s actions, and sometimes engage in iterated steps of reasoning. Open questions exist for how contextual aspects influence strategic choices. When given additional information about their opponents, or the strategic environment, do people’s strategic choices change accordingly? This dissertation uses experimental methods to answer these questions. This work helps to inform foundational models of strategic decision-making. It points to the significant effects of contextual variables on strategic behaviors that must be incorporated into models of choices.