© 2018, © 2018 Educational Studies Association of Ireland. This article considers the relationship between differential homework task difficulty, student engagement and performance across four Irish post-primary school sites. A total of 236 participants completed all elements of this study. All participants were junior cycle students, aged between 12 and 16 years. The study employed a standardised test¿retest approach, with a one week interval between tests. Between testing, participants were randomly subdivided into three cohorts. Each cohort received homework questions of different difficulty levels to complete for one week. The results of this study found that Cohort A, who received the least difficult homework tasks, completed the most non-compulsory questions. Although Cohort A demonstrated higher levels of engagement, no statistically significant difference was found in the change in performance scores of the three cohorts. The results highlight the negative impact of increased task difficulty on student engagement with independent homework tasks. The findings suggest that in order to support student engagement it is important that teachers afford ample opportunity for student success when designing self-directed tasks such as homework.