In order to improve the effectiveness of offender supervision many studies have been conducted into risk factors for delinquency. Evidence was found that debts and crime are interrelated. However, understanding of potential underlying risk factors in this relationship is limited. Results of an analysis of client files (N=250) show that debts among probation clients are highly prevalent and problems with respect to education, work and mental and physical health seem to be important underlying factors in the relationship between debts and crime. In addition, interviews were conducted with both probation workers (N=33) and clients (N=16) to get insight into the possibilities to adequately support clients with regard to debts in order to stimulate successful resocialization. Results underline the importance of paying attention to possible underlying factors to effectively supervise clients.