Munchausen Syndrome (MS) has been widely recognized as a severe manifestation of factitious disorder, a condition where individuals intentionally fabricate or exaggerate symptoms for psychological gratification. It represents a complex diagnostic challenge due to its elusive nature and intricate relationship with various medical conditions. We present a clinical case of a 44-year-old woman observed in the context of Liaison Psychiatry, demonstrating the intricate interplay between chronic medical conditions, psychiatric factors, and the challenges in diagnosing and managing MS. The patient exhibited a history of recurrent hospitalizations, difficult-to-heal injuries, and a pronounced preference for surgical interventions. Despite diagnostic difficulties and poor therapeutic adherence, a multidisciplinary team approach involving plastic surgery, orthopedics, physical medicine, and rehabilitation, alongside Liaison Psychiatry, led to the diagnosis of MS with chronic osteomyelitis, ultimately necessitating a transtibial amputation. The case underscores the importance of early detection, a multidisciplinary approach, and the role of Liaison Psychiatry in managing MS. While early diagnosis may not alter the disease course, it can prevent unnecessary interventions and mitigate associated risks. The case also highlights the need for continuous psychiatric support and family involvement in addressing the recurrence of self-injurious behaviors. Further research is essential to enhance our understanding and develop effective treatment strategies for MS, contributing to improved diagnostic precision and overall management of this challenging psychiatric disorder.