This research is a follow up to an article that I published in the April 2003 (Volume 23, Number 2) edition of Analytic Teaching: The Community of Inquiry Journal entitled "An Integrated Approach to teaching Sociology: Merging Theory and Practice When Studying Women Offenders." It addresses the need to provide experiential learning opportunities for undergraduate students that would result in the enhancement of their critical thinking skills and provide them with a stronger foundation to make informed decisions on complex issues. Specifically, this article focuses on providing my undergraduate students at Pace University with the opportunity to gain formal experience as teaching assistants for college-level Sociology courses that I teach to women at a maximum-security facility in New York. It differs from the first article's illustration of the experiences of students who worked as tutors and mentors and highlights instead the advanced critical thinking skills and analytic outcomes gained by both my undergraduate students and the inmates themselves at the correctional facility as a result if their ongoing interaction. The concepts of Mills, Dewey, and Kolb are applied to the learning experiences and changes in perceptions, particularly in my undergraduate students at Pace, as a result of their role as teaching assistants through weekly and a more than previously structured level of interaction. Specifically, I discuss the accounts of two undergraduate students, one of whom (Marcy) served as a teaching assistant for a Sociobiology course, and the other (Vanessa) for a Topics in Sociology course entitles Women and Work offered at the correctional institution. Finally, I provide a proven methodology for faculty who are interested in incorporating service learning internship opportunities into their liberal arts and/or social sciences courses at correctional institutions. This service learning experience in turn, serves to both provide positive role models for the inmates as well as invaluable insight for the students on the issues that exist within the prison environment.