Great technological leaps in computational capacity and machine autonomy have increased the business community’s expectations of simulators. In joining the conversation on simulators’ ability to reproduce the reality of actual, possible, past, and future worlds, this paper draws on the literature in analytical philosophy on counterfactuals. It identifies three functions of simulations (training, advising, and forecasting) and further inquires into their ontological and epistemological assumptions to show how they limit the quest for reality of higher-performance simulators in each of these three areas. This argument is not only meant to contribute to adjusting scholars’ and practitioners’ expectations and uses of simulations; it also calls for a more in-depth and critical study of the social implications of relying on them.