The keystone of the rehabilitation process is the emotional adjustment to blindness; thus, this adjustment is the overarching goal of Structured Discovery adjustment-to-blindness training. This manuscript proposes a context-specific definition of cheating based on that overarching goal. Major reasons why students cheat include (a) insufficient self-trust, (b) fear, (c) convenience, (d) shame, and (e) not believing that a task is possible for anyone. Students know when they are intentionally selling themselves short, and relationships with students help instructors to understand students’ actions and decisions. Instructors strive to prevent cheating by having good rapport with students and talking to them about it proactively. Training center culture can influence the likelihood of cheating. Instructors must also be able to detect and then correct cheating, and they must be careful how they talk about suspected cheating. Since emotional adjustment is the overarching goal for each student, the emotional adjustment must take priority over skill development and task accomplishment. Illustrative examples are offered from literature and the author’s professional experience.