Non-adherence to health behaviors required for chronic illness self-management is pervasive. Advancing health-behavior theory to include behavioral initiation and maintenance factors, including reflective (e.g., belief- and feedback-based) and automatic (e.g., habit-based) mechanisms of adherence to different treatment-related behaviors could improve non-adherence prediction and intervention efforts. To test behavioral initiation and maintenance factors from an extended common sense self-regulation theoretical framework for predicting medication adherence and physical activity among patients with Type 2 diabetes. Patients (n = 133) in an in-person (n = 80) or online (n = 53) version of the study reported treatment-related (1) barriers, (2) beliefs and experiential feedback (reflective mechanisms of treatment-initiation and short-term repetition), and (3) habit strength (automatic mechanism of treatment-maintenance) for taking medication and engaging in regular physical activity at baseline. Behaviors were assessed via self-reports (n = 133) and objectively (electronic monitoring pill bottles, accelerometers; n = 80) in the subsequent month. Treatment-specific barriers and habit strength predicted self-reported and objective adherence for both behaviors. Beliefs were inconsistently related to behavior, even when habits were “weak”. Experiential feedback from behavior was not related to adherence. Among patients with Type 2 diabetes diagnosis, medication and physical activity adherence were better predicted by their degree of automatic behavioral repetition than their beliefs/experiences with the treatment-actions. Habit strength should be an intervention target for chronic illness self-management; assessing it in practice settings may effectively detect non-adherence to existing treatment-regimens. However, future research and further refining of CS-SRM theory regarding the processes required for such habit development are needed.