A significant proportion of child sexual abuse perpetration is committed by juvenile sexual offenders (JSOs), a subgroup of offenders whose patterns of offending, or "modus operandi," have been found to be markedly different compared to their adult counterparts (Kaufman et al., 1996;Kaufman et al., 1998). Many of these JSOs commit sexual abuse perpetration while acting as a babysitter, or a temporary supervisor to their victim. The present study investigates the routine activities of JSOs and their victims' caregivers that are associated with the JSO being placed into a supervisory role. The study also investigates subgroup differences in the use of modus operandi strategies between JSO supervisors and non-supervisors. Data from this study included 370 JSO participants from four states. Results indicated that parents needs for childcare assistance predicts JSO supervisor status over perpetrators efforts to get the child alone and disruptions to parents lives. Furthermore, JSO acting as a supervisor was associated with more frequent use of modus operandi strategies overall and more frequent use of bribes and enticements to gain their victims compliance. There were no differences between JSO supervisors and non-supervisors on the threats and coercion subscale. Finally, no victim characteristics, JSO characteristics, or disruptions to parents lives, significantly moderated the relationship between JSO supervisor status and strategic grooming. Findings have important implications for research and policy related to child sexual abuse prevention and intervention.ii