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This qualitative study explores the challenges medical students face in achieving genuine collaboration during group tasks and identifies key factors that facilitate the transition from cooperation to collaboration. Grounded theory was employed to analyze data collected from 74 students enrolled in a medical humanities course, including online discussion transcripts, individual learning portfolios, and in-depth interviews. The findings reveal that students with prior collaboration training demonstrated more effective interaction patterns and project outcomes. Furthermore, two critical factors were found to influence collaborative engagement: students’ reliance on previous success with task division and the extent to which instructors consistently applied clearly defined assessment criteria. These insights contribute to a deeper understanding of how collaborative practices can be better supported in medical education.