Recent work has demonstrated that many offenders will choose to serve prison rather than any amount of a community-based sanction. This primarily quantitative research has found that offender-generated exchange rates are influenced by a wide variety of experiences and characteristics. Missing from this literature is a qualitative evaluation of "why" offenders might make this choice. We present qualitative data from 618 probationers and parolees to explain why those who have experienced imprisonment are less willing to serve community sanctions than their counterparts, and more willing to serve prison. Results hold implications for deterrence, recidivism, rehabilitation, and correctional policy issues. (Contains 3 tables and 3 notes.)