Boundary violations occurring in corrections settings require special attention. There is a unique relationship between officers and inmates, governed by policies and procedures as well as ethics in general (e.g., the lack of ability for a person in a controlled environment to consent to a relationship due to power imbalance). Recent high-profile cases between corrections officers and inmates demonstrate the complexities inherent in these relationships. We examine several recent cases and offer analysis of the factors leading to these dangerous encounters. We discuss how a special relationship develops between a corrections employee and an inmate and how that can lead to blackmail, the introduction of contraband to the prison, or other illegal activity. It is easy to state that one should not engage in sexual encounters, but it is harder to discuss and identify feelings that develop in correctional settings, such as transference and counter-transference feelings in a therapeutic relationship. Lessons of professionalism from the doctor–patient relationship parallel the relationships between officers and inmates.