In many work and decision situations, realizing cooperation among individuals is important. However, decision making environments of individuals are far from stable, resulting in changes in task complexity and the social settings they encounter. We argue that past experiences with cooperative behavior can result in different cooperative norms and expectations about the behavior of others and will have an effect on an individual’s subsequent behavior in new situations. This study experimentally investigates these dynamics of cooperative behavior in social dilemmas and addresses the role of communication to provide empirical evidence about a cognitive mechanism that may lead to these spillovers. Specifically, the experimental design randomly assigns subjects to one type of repetitive interactions in the first social dilemma (single partner or different partners) and we then examine how this impacts the propensity to behave cooperatively in subsequent social dilemmas with unfamiliar partners (either single or different). Because of the variety in complexity of decision-making environments in practice, we do so by examining behavioral spillovers across three different social dilemmas that vary in difficulty to make cooperation successful. Our findings show that individuals cooperate more during initial interactions with a single partner. More importantly, this has positive spillover effects for subsequent behavior and communication, even to settings without repeated interactions with a single partner. However, environmental conditions affect the ability to transfer established norms of cooperation to subsequent interactions, as an initially learned cooperative norm is gradually replaced by a more competitive attitude when individuals start to interact with unfamiliar others in a setting in which cooperative success is more difficult to achieve. Our findings illustrate the power of repeated interactions for establishing and sustaining cooperation in other settings and enhance understanding of how cooperative decisions can be shaped by both incentives and the broader behavioral context of individuals.