Level II fieldwork serves as a critical component of occupational therapy (OT) student education during which students develop and refine skills to become practicing clinicians; however, research on student characteristics that influence the fieldwork experience is limited. The purpose of this study was to explore student mental health, confidence, and mindful self-care practices throughout Level II fieldwork. Ten OT students completing Level II fieldwork participated in this study by completing surveys during the first week, midpoint, and final two weeks of their second Level II fieldwork experience. Each survey contained Cohen's Perceived Stress Scale (PSS-10), the Student Confidence Questionnaire, and the Mindful Self-Care Scale (MSCS)-SHORT to investigate student stress, confidence, and self-care respectively. Kruskal-Wallis H tests revealed that stress was highest during the first two weeks of fieldwork, confidence increased significantly from the beginning to the end of fieldwork, and self-care practices remained stable over time. Additionally, correlation analyses revealed a positive relationship between confidence and self-care (r[subscript s] = 0.78, p < 0.01), a negative relationship between stress and confidence (r[subscript s] = -0.78, p < 0.01), and a negative relationship between self-care and stress (r[subscript s] = -0.69, p = 0.03). These results have implications for OT students, educators, and fieldwork supervisors as stress reduction techniques and confidence building may be beneficial for student outcomes before and during Level II fieldwork to maximize success through this transitional period from student to clinician.