This study explored the experience of occupational therapists who encountered counterproductive events during their fieldwork training. Interviews were conducted to gather information regarding the participant's perception of factors that contributed to a negative fieldwork experience. The results were divided into major categories: (1) the role of the supervisor, (2) poor supervisory characteristics, (3) the fieldwork infrastructure, (4) misconceptions in the fieldwork experience, (5) student coping strategies, (6) student responses, (7) positive outcomes, (8) negative consequential outcomes, and (9) cycle of the ineffective fieldwork experience. The results showed challenging supervisory events were the major factor in contributing to a negative fieldwork experience; however, the situation was magnified by other factors such as lack of academic program support. To help prevent this phenomenon from occurring or to minimize negative outcomes, positive resolutions such as solutions to dilemmas presented by the current health care system may minimize the difficulties impinging on fieldwork in occupational therapy.