Although a recent update on the functional theory of counterfactual thinking suggests that counterfactuals are important for behavior regulation, there is some evidence that counterfactuals may not be functional for everyone. Two studies found differences between maladaptive and high personal standards perfectionism in the functionality of counterfactuals and variables relevant to behavior regulation. Maladaptive but not personal standards perfectionism predicted making more upward counterfactuals after recalling a negative event and was linked to a variety of negative markers of achievement. Maladaptive perfectionism was associated with making controllable, subtractive, and less specific counterfactuals. High personal standards perfectionism moderated the effects of maladaptive perfectionism on counterfactual controllability. Generating counterfactuals increased motivation for personal standards perfectionists relative to a noncounterfactual control group but had no effect on motivation for maladaptive perfectionists. The findings suggest a continuum of counterfactual functionality for perfectionists and highlight the importance of considering counterfactual specificity and structure.