Objective: This study examined predictors of medication administration hassles reported by intergenerational dementia family caregivers. Methods: A sample of 53 women who aided a cognitively impaired older adult with healthcare and who identified as inter-generational caregivers provided self-report medication management and psychosocial data. Results: Hierarchical multiple regression analyses revealed that six independent variables hypothesized for this model, the total number of prescription medications managed by caregivers, educational attainment, care-recipient functional impairment, care-recipient cognitive impairment, caregiver depressive symptomatology, and self-reported feelings of preparedness for the caregiving role together significantly predicted caregiver medication administration hassles scores F(1, 48) = 4.90, p = .032, and accounted for approximately 25% of the variance of self-reported hassles (adjusted R2 = .247). Discussion: Future interventions may reduce medication-related hassles by providing psychoeducation about healthcare, medication management, and strategies for coping with care-related stressors and depressed mood.