Purpose The purpose was to identify trajectories of medication taking among patients with diabetes and investigate correlates of these trajectories using the information–motivation–behavioral skills (IMB) model. Methods This study employed a descriptive correlational, longitudinal design using convenience sampling. The participants were 96 adults with diabetes from an outpatient diabetes clinic at a university-affiliated hospital. Medication taking was assessed at 3 time points: baseline, 6 months, and 12 months. At baseline, study variables based on the IMB model were measured: medication knowledge (information), motivational readiness and social support (motivation), and medication self-efficacy (behavioral skills). Group-based trajectory modeling was used to identify medication-taking trajectories, and multinomial logistic regression was used to assess factors associated with medication-taking trajectories. Results Three distinct medication-taking trajectory groups were identified: “high medication taking,” “increasing medication taking,” and “low medication taking.” Higher medication knowledge was associated with the high and increasing medication-taking trajectory groups. Motivational readiness was associated with the high and increasing medication-taking groups. In contrast, higher medication self-efficacy was associated only with the high medication-taking group, not with the increasing and low medication-taking groups. Conclusions The findings suggest that knowledge, motivational readiness, and self-efficacy are essential in IMB model-based intervention strategies across dynamic medication-taking patterns to enhance medication taking. Health care providers can help patients with diabetes improve medication taking by understanding their medication-taking trajectories and their correlates. Strategies that enhance medication self-efficacy are essential for patients in the increasing and low medication-taking groups.