This study explored the feasibility of covering nicotine replacement therapy (NRT) and paying for pharmacist-delivered smoking cessation counseling at the time of NRT pick-up for low-income, managed Medicaid and Basic Health Plan (a state insurance program) enrollees. A prospective pilot intervention was used at two community health centers (CHCs) and two community pharmacies. Participants were adult managed-Medicaid or Basic Health Plan enrollees who attended the pilot CHCs and smoked. An innovative insurance benefit that included coverage for NRT and $15 payment to the pharmacist to deliver cessation counseling with each prescription fill. Proportion of eligible patients who used the cessation benefit and patient and pharmacist satisfaction with the intervention. During the 9-month intervention, 32 patients at the pilot clinics were referred for NRT and pharmacist-delivered counseling. This number represented roughly 5% of eligible smokers. Of these, 26 received NRT with concomitant pharmacist-delivered cessation counseling at least once. Recipients reported a high level of satisfaction with this intervention. Pharmacists indicated they would continue providing counseling if reimbursement remained adequate and if counseling lasted no longer than 5–10 min. However, 12 (38%) who were referred were no longer insured by the sponsoring plan by the end of the 9-month pilot period. Pharmacist-delivered cessation counseling may be feasible and merits further study. More importantly, this pilot reveals two key obstacles in our low-income, culturally diverse setting: low participation and rapid turnover of insureds. Future interventions will need to address these barriers.