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Over the last decade, mental health probation caseloads have become increasingly common - focused on working with offenders with mental illness (OMIs). As a result, scholars have examined the structure and design of these programs, investigated their overall effectiveness, and considered how probation officer demographics and personality traits can impact the experience of OMIs. Less attention, however, has been placed on investigating how the OMI’s assigned to these programs consider their experience. The current study uses a convenience sample of OMIs on a mental health caseload to explore the perspective of the individual offender. Semi-structured qualitative interviews were completed with a convenience sample of 111 OMIs on a mental health specialty caseload in the state of Arizona between 2012 and 2013. Using the constant comparative method of analysis, the offender’s perspective is examined in detail regarding individual viewpoints about the relationship with his/her probation officer, and the overall experience of being a person with a significant mental illness on a mental health caseload.