African American (AA) adults are disproportionally affected by type 2 diabetes and are diagnosed at an earlier age, but are less adherent to diabetes medications compared with the general population. This qualitative study sought to describe the experiences of taking diabetes medications among midlife AA men and women with type 2 diabetes and to identify factors that influence these experiences. Fifteen AAs completed semistructured interviews. Using the Roy adaptation model, thematic analysis coded for both adaptive and ineffective experiences. Adaptive experiences included self-confidence in one’s ability to control diabetes, a belief in the value of diabetes medication, assuming responsibility for one’s health, developing a routine for taking medication, and positive relationships with the care team. Ineffective experiences for medication taking included: feeling powerless over diabetes, self-blame, and fear. One’s self-concept as a person with diabetes, as well as assuming the role of “medication taker,” were prominent themes.