Prison educators and vocational trainers are instrumental in prisons given their roles in teaching and preparing prisoners for a successful reintegration into the community. Although prior research has explored the impact of vocational and educational programs on offender recidivism, scant attention has been paid to the work experiences of prison educators and instructors. The current study thus examines perceptions of supervision and organizational operations among a sample of 263 educational and vocational staff employed in the Federal Bureau of Prisons. A key contribution of this study is the inclusion of new organizational-level variables (e.g., a prison's average institutional tenure and average institutional commitment) as predictors of perceptions of the prison work environment. Hierarchical Linear Models (HLM) identified that efficacy with inmates was the strongest predictor of perceptions of both supervision and organizational operations. Age, supervisory status, Hispanic ethnicity, and the average institutional tenure were also significant predictors of both outcome measures. Security level, inmate gender composition, average institutional commitment, the amount of contact with inmates, and race had different effects on the dependent variables. The implications of these findings and directions for future research are discussed. (Published Abstract)