The current study investigated perfectionism and procrastination from the trait and cognitive perspectives and addressed how they relate to components of a personal orientation toward failure. A sample of 327 undergraduate students completed three perfectionism measures (i.e., Frost Multidimensional Perfectionism Scale, Hewitt-Flett Multidimensional Perfectionism Scale, and Perfectionism Cognitions Inventory), two procrastination measures (i.e., Lay Procrastination Scale and Procrastinatory Cognitions Inventory), and measures of fear of failure and overgeneralizing failure. Correlational analyses showed that the composite trait dimension of perfectionistic concerns and the cognitive dimension of perfectionistic automatic thoughts had modest links with trait procrastination but much stronger links with the cognitive measure of procrastinatory automatic thoughts. All perfectionism and procrastination measures were significantly correlated with fear of failure and overgeneralization of failure. More extensive analyses showed that fear of failure mediated trait and cognitive pathways between perfectionism and procrastination, and the overgeneralization of failure mediated most pathways. Other evidence supported a sequential mediation between perfectionism and procrastination (i.e., fear of failure followed by the overgeneralization of failure). Overall, the results suggest that procrastinating perfectionists have a cognitive hypersensitivity to failure and a potentially debilitating form of perfectionistic reactivity characterized by overgeneralizing failures to the self. The theoretical and practical implications are discussed.