Although performance feedback is widely employed as a means to improve motivation, the efficacy and reliability of performance feedback is often obscured by individual differences and situational variables. The joint role of these moderating variables remains unknown. Accordingly, we investigate how the motivational impact of feedback is moderated by personality and task-difficulty. Utilizing three samples (total N = 916), we explore how Big Five personality traits moderate the motivational impact of false positive and negative feedback on playful, neutral, and frustrating puzzle tasks, respectively. Conscientious and Neurotic individuals together appear particularly sensitive to task difficulty, becoming significantly more motivated by negative feedback on playful tasks and demotivated by negative feedback on frustrating tasks. Results are discussed in terms of Goal-Setting and Self Determination Theory. Implications for industry and education are considered.