To determine patient characteristics associated with achieving and sustaining blood pressure (BP) targets in the Adherence and Intensification of Medications program, a program led by pharmacists trained in motivational interviewing and authorized to make BP medication changes. We conducted a retrospective cohort study of patients with diabetes and persistent hypertension in Kaiser Permanente and the Department of Veterans Affairs. Using two-level logistic regression, baseline survey data from 458 program participants were examined to determine patient characteristics associated with (1) discharge from the program with a target BP (short-term success) and (2) maintenance of the target BP over a nine-month period (long-term success). In multivariable analyses, patients who screened positive for depression or had a higher baseline systolic BP were less likely to achieve short-term success (adjusted odds ratio (AOR) 0.42 [95% confidence interval (CI): 0.19-0.93], p?=?0.03; AOR 0.94 [0.91-0.97], p?0.01; respectively). Patients who reported at baseline one or more barriers to medication adherence were less likely to achieve long-term success (AOR 0.50 [0.26-0.94], p?=?0.03). Although almost 90% of patients achieved short-term success, only 28% achieved long-term success. Baseline barriers to adherence were associated with lack of long-term success and could be the target of maintenance programs for patients who achieve short-term success.