Benzodiazepines (BZ) are often diverted from legal sources to illicit markets at various points in the distribution process beginning with a pharmaceutical manufacturer, followed by healthcare providers, and finally, to the intended users. Little is known about the extent of BZ diversion involving distribution points directly related to healthcare sources versus points further down the distribution chain. The present study examines the scope of BZ diversion, and the association between BZ dependence and the direct utilization of particular healthcare-related diversion sources among a diverse sample of prescription drug abusers in South Florida. Cross-sectional data were collected from five different groups of drug users: methadone-maintenance clients (n = 247), street drug users (n = 238), public-pay treatment clients (n = 245), private-pay treatment clients (n = 228), and stimulant-using men who have sex with men (MSM; n = 249). Findings suggest that those who are ages 26 to 35 years old, non-Hispanic White participants, private-pay treatment clients, those who are insured, and those with higher incomes had higher odds of utilizing healthcare diversion sources. Those who reported BZ dependence had 2.5 times greater odds of using a healthcare source to obtain BZs than those who did not meet criteria for dependence.