Self-medication is increasingly prevalent among healthcare students, raising concerns about the adequacy of current medical education in promoting safe medication practices. This study aimed to assess the frequency, motivations, and perceptions of self-medication among medical and pharmacy students and to identify educational gaps. A cross-sectional survey was conducted using a structured, anonymous questionnaire distributed to medical and pharmacy students at a single academic institution. The questionnaire assessed self-medication frequency, substances used, motivations, perceived risks, confidence in knowledge, sources of information, and attitudes toward curriculum improvements. Over 50% of participants reported practicing self-medication at least once a month. The most commonly used substances were analgesics and dietary supplements. Main motivations included recognition of symptoms, confidence in personal knowledge, and avoidance of waiting times. Despite receiving university instruction on self-medication risks, students continued to self-medicate, with many relying on the internet as a primary source of information. Only 8% felt very confident in counseling patients on self-medication. A majority (over 70%) expressed a strong interest in integrating dedicated educational modules into the curriculum. There is a clear need for improved, practice-oriented education on self-medication. Future interventions should focus on interdisciplinary teaching, digital literacy, and simulation-based training to foster safer medication practices.