Counterfactual thinking involves reflecting on how a given outcome may have been different. Such thoughts are centred on how the outcome could have been better (upward counterfactuals) or worse (downward counterfactuals), with most previous research focusing on a specified direction of these thoughts in response to a negative outcome. The current research explored how considering either one or both directions of counterfactuals after a positive outcome in an anagram task may be related to changes in affect and subsequent task performance. Undergraduate psychology students (N = 86) either imagined only better or worse counterfactual alternatives in response to their anagram task performance, or considered both better and worse alternatives. Mood ratings before and after counterfactual generation were assessed, with self-efficacy, preparedness, and task performance also examined. Mood ratings significantly declined in the upward only and downward followed by upward conditions, with no change occurring in the downward only or downward last conditions. Upward counterfactuals also resulted in a significant increase in the proportion of time for anagram task completion. The findings demonstrate that the expected preparedness effects of counterfactual generation did not prevail after a positive outcome, and that a recency effect on mood occurs for the last counterfactual generated.