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 R= .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.