OBJECTIVE: Although the Social Security Administration frequently assigns family members to serve as representative payees for relatives with psychiatric disabilities, few studies have examined characteristics associated with these payee arrangements or the perceptions of the individuals involved in them. METHODS: One hundred participants (50 dyads of consumers with psychiatric disabilities and their representative payees from their family) were interviewed for data on perceived benefits and problems of the payeeship, knowledge of payee guidelines, the consumer-payee relationship, arithmetic and money management skills, and payeeship characteristics. RESULTS: Most consumers and payees believed that payeeship led to greater living stability; however, 36% of consumers and 50% of payees reported disagreement and conflict. Some consumers thought payeeship reduced their autonomy, although payees were less aware of this. Consumers and payees showed gaps in knowledge of payeeship, with only 28% correctly recognizing that payeeship did not last indefinitely. Both groups showed deficiencies in money management skills and basic arithmetic abilities; in these domains, there were no significant differences between payees and consumers. Risk of conflict was elevated when consumers had better money management skills and when payees had not completed high school. CONCLUSIONS: Although payeeship was beneficial, the data revealed potential problems in skills and knowledge about representative payeeship among consumers and payees. Efforts by policy makers and clinicians to increase collaboration between payees and consumers and to improve accurate knowledge of payeeship could help address its downsides.