Study data were obtained from semistructured interviews with 40 postsecondary correctional educators employed by Wilmington College in Ohio. The semistructured interview format encouraged respondents to identify issues central to their experiences, as well as core issues concerning professional and personal histories, social demographics, personal teaching styles, and perceptions of programmatic and institutional relationships. Correctional educators designed individual strategies to manage obstacles inherent in correctional facilities. Two distinct problem areas presented challenges and difficulties in the educational process, environmental limitations and complex inmate-faculty interactions. Most correctional educators said adhering to security measures and lack of adequate facilities and resources made it difficult to pursue educational goals. They also indicated the structure of institutional routines inhibited meaningful interaction with students and other faculty members outside the classroom. How inmates perceived and reacted to instructors, how inmates tested and manipulated instructors, and how cross-sex interactions were structured and managed complicated the work of correctional educators. Inmate perceptions of instructors sometimes led to tensions and interpersonal conflicts in the prison setting. Strategies to minimize environmental and interactional problems are described. 43 references and 1 note