Although many interventions are effective for health behavior initiation, maintenance has proven elusive. Interventions targeting maintenance often extend the duration with which initiation content is delivered or the duration of follow-up without intervention. We posit that health behavior initiation and maintenance require separate psychological processes and skills. To determine the value of operationalizing maintenance as a process separate from initiation, we conducted a pilot study of a telephone-delivered intervention to assist people in transitioning from behavior initiation to maintenance. Participants were 20 veterans who had initiated lifestyle changes during a randomized controlled trial of a cholesterol reduction intervention. After completing the randomized controlled trial, these participants were enrolled in the pilot maintenance intervention, which involved three monthly telephone calls from a nurse interventionist focusing on behavioral maintenance skills. To evaluate the feasibility and acceptability of this intervention, we assessed recruitment and retention rates as well as 4-month pre–post changes in health behaviors and associated psychological processes. We also conducted individual interviews with participants after study completion. Although not powered to detect significant changes, there was evidence of improvement in dietary intake and of maintenance of physical activity and low-density lipoprotein cholesterol during the 4-month maintenance study. Participants found it helpful to plan for relapses, self-monitor, and obtain social support, but they had mixed reactions about reflecting on satisfaction with outcomes. Participants accepted the intervention and desired ongoing contact to maintain accountability. This pilot maintenance intervention warrants further evaluation in a randomized controlled trial.