Most of the extant literature on prison violence has explored inmate-on-inmate assaultive behaviors rather than inmate-on-staff assaults. In addition, the bulk of this past literature considered only one level of an analysis, the inmate or the prison, while ignoring the importance of prison context on inmate behavior. This study enhances past research by combining both inmate-and prison-level data into a multilevel model predicting the likelihood of inmate-on-staff assaults. Self-report data from more than 1,000 inmates and 30 prisons revealed that, at the inmate level, age and aggression were the most robust predictors of inmate-on-staff assaults. In terms of contextual effects, inmates housed in prisons with a greater proportion of non-White inmates and a larger staff-to-inmate ratio were more likely to assault prison staff members. Policy implications and suggestions for future research are discussed.