Inherent complexities exist when providing therapeutic services in correctional settings. Working within a correctional setting can also be demoralizing due to therapeutic, systemic, and ethical issues that are rarely encountered in most other settings. One way to minimize this discouragement and help ensure successful treatment when working with inmate-clients in these settings is developing and attending to the therapeutic alliance. However, there are unique threats to the therapeutic alliance that the correctional mental health clinician must consider, but also unique opportunities. From a psychodynamic perspective, this paper explores the many challenges and opportunities to building, strengthening, and repairing the therapeutic alliance likely to arise in correctional settings. A case vignette is used to illustrate several therapeutic alliance experiences that can manifest while working with inmate-clients, including factors that have the potential to rupture and/or repair the therapeutic alliance. Suggestions for establishing and maintaining the therapeutic alliance with inmate-clients are then offered and discussed.