Background: Arthroscopic shoulder stabilization is known to have excellent functional results, but many patients do not return to their preinjury level of sport, with return to play rates reported between 48% and 100% despite good outcome scores. Purpose: To understand specific subjective psychosocial factors influencing a patient’s decision to return to sport after arthroscopic shoulder stabilization. Study Design: Case series; Level of evidence, 4. Methods: Semistructured qualitative interviews were conducted with patients aged 18 to 40 years who had undergone primary arthroscopic shoulder stabilization and had a minimum 2-year follow-up. All patients participated in sport before surgery without any further revision operations or shoulder injuries. Qualitative data analysis was performed in accordance with the Strauss and Corbin theory to derive codes, categories, and themes. Preinjury and current sport participation was defined by type, level of competition, and the Brophy/Marx shoulder activity score. Patient-reported pain and shoulder function were also obtained. Results: A total of 25 patients were interviewed, revealing that fear of reinjury, shifts in priority, mood, social support, and self-motivation were found to greatly influence the decision to return to sport both in patients who had and had not returned to their preinjury level of play. Patients also described fear of sporting incompetence, self-awareness issues, recommendations from physical therapists, and degree of confidence as less common considerations affecting their return to sport. Conclusion: In spite of excellent functional outcomes, extrinsic and intrinsic factors such as competing interests, kinesiophobia, age, and internal stressors and motivators can have a major effect on a patient’s decision to return to sport after arthroscopic shoulder stabilization. The qualitative methods used in this study provide a unique patient-derived perspective into postoperative recovery and highlight the necessity to recognize and address subjective and psychosocial factors rather than objective functional outcome scores alone as contributing to a patient’s decision to return to play.