Building on research exploring repeated risky choice and strategic decisions, we tested what constitutes a sufficiently satisfactory outcome to prompt people to repeat their actions. Our programmatic investigation (total N > 1400) examined incentivised choices between pairs of binary-outcome options, with immediate feedback for obtained and forgone outcomes. Across experiments, we varied the payoff structure for the possible outcomes. Within experiments, we manipulated the probabilities associated with each outcome, either across choice tasks (Experiments 1-3) or unannounced within a task (Experiments 4-6). We compared the roles of disappointment (receiving the lower outcome from an option), regret (receiving a lower outcome than the forgone payoff), and the relative average value of the options, as drivers of choice. Across all experiments and most tasks and conditions, implied regret exerted a stronger influence on subsequent choices than implied disappointment, the ratio of options’ average values, or the absolute magnitude of losses or gains. Our findings illustrate how responding to regret can help people choose well, and suggest how descriptive decision models might be improved.