A growing body of literature explores how participation in programming in correctional institutions predicts inmate misconduct. Theory and extant research suggest that engagement in structured and prosocial activities promotes positive behavioral and emotional outcomes, while idleness has a negative impact on inmate behavior and well-being. However, the literature that examines these relationships is largely based on qualitative methodology, small samples, and prison population. Using data from the 2002 Survey of Inmates in Local Jails, this study fills the gap in the literature by examining the associations between engagement in various activities in jail and inmate misconduct. This study also explores individual and jail-level factors that predict inmate engagement in different activities in jails. The results show that watching TV and working in jail are associated with lower misconduct, whereas recreation and reading are associated with higher levels of several types of misconduct. The data also reveal that certain personal and institution-level factors predict the extent of engagement in formal and leisure activities.