Using a cross-sectional design, this study examined the relationships between parental guilt, shame, need frustration, and homework stress in students with learning disabilities (LD) and typically developing students (TD) and their parents. One hundred and eight parent-child dyads (54 LD, 54 TD) completed questionnaires to assess homework stress, parental need frustration, guilt, and shame. Parents of students with LD reported more stress, need frustration, shame, and guilt than parents of TD students. For the LD group, shame mediated the association between parental need frustration and parental and child stress whereas guilt mediated the association between parental need frustration and parental stress. The theoretical and practical implications for lessening homework stress for students with LD and their parents are discussed.