In 2008, almost 40% of Aboriginal and Torres Strait Islander students enrolled in the Graduate Diploma in Indigenous Health Promotion at The University of Sydney failed to complete the course. Although this was not considered unusual when compared to previous years, the decision was made to investigate why so many students struggled to meet the expectations of a course that was pedagogically progressive, culturally affirming, taught by highly regarded academics and strongly supported by the university and its stakeholders. A qualitative study using in-depth semi-structured interviews was conducted, and many complex and interrelated issues were explored. One issue that was raised both unexpectedly and emphatically by almost half the study participants who completed the course was the unintentional stifling of individual student effort and achievement through the development of co-dependent relationships between academic staff and students. This article presents the data relevant to this particular issue, reflects on the findings, and outlines some of the strategies implemented since this study commenced that have contributed to a healthy completion rate of 98% over the past 3 years.