Objectives: This article describes a pilot test of an individually tailored program to improve community living and health self-management skills in older adults with serious mental illness. Method: This study provided the Helping Older People Experience Success—Individually Tailored (HOPES–I) intervention, an adaptation of an empirically supported, manualized, group-based skills training program shown to improve community functioning, psychiatric symptoms, self-efficacy, and receipt of preventive health. HOPES–I targets 5 skill areas: leisure time, communication, independent living, friendships, and health self-management. We enrolled 47 adults age 50 and older (mean age = 62) with serious mental illness (38% schizophrenia spectrum, 62% mood disorders). Trained HOPES–I coaches evaluated participants’ skills and functioning and engaged them in shared decision-making to select which curricular areas to receive. Participants received 1 HOPES–I session per week for 9–12 months, with assessments of overall psychosocial functioning and the 5 skill areas targeted by the program at baseline, postintervention, and at 3 and 6 months. Results: Participants with baseline impairments in overall functioning and in each of the skill areas targeted by the program demonstrated significant improvements on related outcome measures. Selection of specific HOPES–I curriculum was not associated with level of impairment in associated skill areas at baseline, but participants with more impairment overall chose and completed more curriculum modules. Conclusions and Implications for Practice: The results of this study support the feasibility and potential benefits of an individually tailored skills training program for the rapidly growing and vulnerable group of older people with serious mental illness.