High rates of rearrest and recidivism, especially among drug-involved individuals, are of grave concern for the justice system and society at large. This chapter looks at the factors affecting recidivism rates of substance-involved individuals involved in the justice system. We begin by considering the complexity of measuring recidivism and the meaning of this concept; the term is fraught with difficulties due to the complexities of generalizing findings across studies with varying sampling frames and time-frames for follow-up, and differences in the types of recidivism events studied. Recent research illustrates that recidivism rates among drug users vary by drug of choice and are typically higher among individuals who use amphetamines, heroin, and/or cocaine. Recidivism rates may also vary depending on the presence of certain comorbid factors, although this is an emerging area of research. Factors that appear to elevate recidivism rates include personality disorders, co-occurring substance abuse and mental health disorders, other psychiatric disorders, and other serious mental illness. The location of an individual’s residence also appears to impact the recidivism rate, possibly mediated by the presence or absence of various protective factors in the community. While the nature of the relationship between drugs and crime is still unclear, the same is true for our understanding of recidivism among substance users in the justice system. There is a need for a greater understanding of the relationship between substance use and recidivism, in order to fill existing knowledge gaps.